Even though I’ve been writing this blog for nearly ten years, I’ve realized that I haven’t done much on footwear.
At the very least, they haven’t been talked about in the same, pseudo-philosophical way (read: pretentious) as I’ve talked about other garments. The blog posts about shoes, like the ones about Paraboots and Chukkas, have just been about appreciating something specific, the journey to buying them, and then making the outfits I’ve always wanted to make with them. But perhaps it’s time to dive a bit deeper, especially now that I’ve largely “completed” my shoe collection and have since focused on just…wearing them. (I also don’t think that each of my purchases requires a blog post).
I was reminded of this sentiment when a few months ago, my internet-menswear friend Acute Style asked me if I was planning on how I pick the “right” shoe when I make my outfits. Like I said, I do have a sizable collection that is more than just a dress shoe for suits and sneakers for being casual. Picking the “right” shoe was set to be a great topic worthy of a typical Ethan deep dive.
After all, when you’re a beginner, the “right shoe” is mainly about getting something that has good make and has a bit more of an intention design and perhaps is pointed more directly in a general aesthetic. It’s about upgrading your Ecco Helsinki into something at least like an AE Park Avenue (though a Bass Weejun will be more interesting and will most likely get more mileage). But we’re not beginners. We’ve graduated past bike toes and cooked exercise sneakers. You have developed taste and hopefully a POV. And like me, this has probably resulted in a hearty collection of good shoes. So what does the “right” shoe mean now?
Shoes may take up such little “real estate” in our outfits, but that doesn’t mean we get to gloss over the effect that shoes can have on your outfit and your overall style. I’ve often heard of the idiom “shoes make the outfit” but I guess I haven’t really been critical of what that means, which is surprising considering the importance I place on expression and cohesiveness. But that’s where this blog post comes in, where we’re able to get pretentious and exercise our own experiences with semiotics to see just how we look at footwear and what goes into picking the one we wear with our chosen outfit.
And spoiler alert, picking a shoe is actually quite easy. It should be second nature, almost like a reflex.
Shoes as Anchors and On Formality
A grey suit, plain shirt, and solid tie is quite formal. So black shoes it is!
Simply put, I consider footwear to be the anchors of an outfit’s vibes and ultimately your POV. This is the simplest way I can put it and if you disagree with this premise, you can probably just skip the entire blog post.
Formality is obviously one of the biggest factors in determining vibe. In menswear, most leather footwear tend to be considered “dressy” and “formal” whereas sneakers are considered casual. While there is still a bunch of nuance thanks to the current world that no longer adheres to strict formality rules (loafers and oxfords are more or less perceived as the same in the mainstream), the broad ideas are immediately helpful in narrowing down your choices or at least pointing you in the right direction to go.
It definitely helps to decide what vibe you want as you make the outfit, since it makes every decision flow quickly and naturally. Wearing a conservatively styled suit with a black leather dress shoe helps firmly plant you in the “formal” realm, relatively speaking. Wearing jeans with canvas sneakers is an easy way to say that you are dressed casually. Simple, right? It can also get a little fun as you add nuance to your outfits’ expression.
A wool suit with knit wear (a relatively casual outfit compared to one with a tie) can either emphasize a semblance of formality with a leather shoe. Or it can be subverted by pairing it with sneakers, making the suit a bit more casual (again relatively speaking). Jeans, khaki chinos or even shorts (all casual things) can be “dressed up” by wearing leather lace ups or loafers.
Of course, this gets interesting when you get even more nuanced with your vibes/formality, like a merch tee with a blazer and a trouser, fatigues with a tie, and so on. It can seem shoe, but that’s why the “right” shoe will be based on what formality level you want to anchor down on: leather dress shoes to reinforce formality (relatively speaking) and sneakers/non-dress shoes for being casual.
On that note, I’ve been told that friends, even non-menswear ones, are often told that they look dressed up simply by wearing a leather shoe with their jeans. As a result, they often play that up when they want to elevate a look even if they aren’t wearing a trouser or sportcoat. I know that I’ve had the same experience. I feel formal in a leather shoe and I feel casual in a sneaker or other (non-dress shoe), even if the other elements of the outfit may have “traditionally” stated otherwise.
This means that the “right” shoe choice will not only anchor your aesthetic in terms of formality but in mindset as well, even if it’s playing “tradition” straight or if you want to be a little subversive with your choices. Shoes are quite powerful indeed.
On Shoe Color
Brown shoes here are not just about playing up the casual-tailoring but also the overall earth tones of the outfit!
The color of our footwear is also an important consideration, especially as it is inherently linked to our perceptions of an outfit’s formality. This is especially true when it comes to leather footwear (aka ”dress” shoes). Broadly speaking, black is formal, brown is “casual”, and other colors even more so. Of course there is nuance here as well, such when we take material into account (skin leather vs suede), but it is still a useful guide.
But a shoe’s color is more than just checkboxes stating whether you are “formal” or not. They are still garments, components of an aesthetic-object (the outfit). Pretentious language aside salad, the actual “color theory” function is still at play (I’m using this loosely), where tones and hues can provide contrast and ultimately visual weight to the effect of an outfit.
This is best shown when we think about how we play into or subvert the color-temperature of your outfit. In most cases, this does go hand-in-hand with formality, where a navy suit (a cold-toned business suit) is emphasized with black shoes. There is the opposite case where you can wear a black shoe with a taupe or khaki suit, which provides contrast while still functioning as a visual color-anchor, drawing the eye down (or something idk). Of course, you can also forgo strong contrast and instead, use a tonal shoe to anchor the entire color palette of the outfit. Think of a white buck or cream canvas sneaker with a tan suit (or even a white linen one), which yes, is casual, but also shows some fun with color theory (I think??).
Of course, this is all just a surface level way of thinking of how shoes play into an outfit. I don’t want this to come across as some cold formula that is devoid of personality. There is obviously more at play here. After all, we don’t get dressed to just be formal or by putting together colors that we like. Outfits are a mixture of authenticity, context, and personal narrative, making clothing an opportunity for storytelling instead of just functional communication. I’ve discussed as much with Cinematic Dressing where we leverage the history and codified nature of our garments and outfits to express a facet of who we are and what we like.
And that brings me to the main tenet of my approach, where I see the “right” shoe as the anchor for your particular outfit’s Theme (and its Variations).
Shoe Semiotics, Contextual Roots, and Playing it Straight
A khaki 3-roll-2 suit, button down collar shirt, and repp stripe tie almost cries out for penny loafers.
Shoes are just like any garment found in classic menswear: each type of shoe is full of history and context which not only ties them to particular levels of formality but to certain genres and subcultures. Every shoe points toward some kind of aesthetic. And since they are the “last” item that you put on (but not necessarily the last one you may have chosen), shoes function as the thematic anchor (or capstone) to your outfit. It’s the final word in your outfits story and I believe that they carry just as much gravitas as you would expect.
It’s also quite easy and almost like a reflex to most menswear enthusiasts.
Let’s look at penny loafers. They are not just casual leather shoes (at least in comparison to oxfords and derbies) but ivy-trad/preppy casual leather shoes. Wearing them as part of an outfit is a great way to point toward the ivy look and perhaps even double down on it. Add in color (brown is casual, black is “more formal”) and you’re adding nuance to your ivy outfit! So you see, the “right” shoe choice is not just about formality or color, but about continuing the fun exercise of expressing a Theme or Narrative. It just makes picking the “right shoe” incredibly easy, especially when you’re trying to pick from a collection (that you no doubt have).
If I’m wearing something stereotypically ivy-trad, like an OCBD and repp tie, it just makes sense for me to choose penny loafers as the “right” shoe to wear as it doubles down on the Theme. If a lace-up was needed, then longwings or split toes (per historical photos and illustrations). In that same vein, if I’m going for something western with jeans and a denim shirt, naturally a pair of cowboy boots is the way to go; this would also go well for a 70s look, where there was plenty of western influences). A yuppie wears horsebits where as a contemporary trad-menswear guy would lean on tassel loafers; #menswear favors suede loafers. Esquire Man illustrations have a penchant for brown suede lace ups (especially single monks).
There is obviously some nuance with casual shoes, but the same sort of Thematic Uniform still applies. Ivy-trad casual would probably wear canvas deck shoes or wallabees; desert boots would be worn if you wanted to bridge the gap. Contemporary ivy-casual likes a vintage dad sneaker or something rugged like Danner boots. Converse looks good when going for a general “vintage casual” (1940s-1960s) look. Whatever the case may be, there will always be a natural pick for an Outfit that is grounded in a POV.
But how do you pick a shoe when your outfit isn’t strictly following a tried and true menswear “core”?” After all, Mixing genres of garments and adding nuance to an outfit is a big part of this little menswear hobby. But if you’re like me, it helps to add some semblance of a theme, to reign in the different ideas of the outfit. And the “right” shoe will do that, all through Forced Versatility.
On Nuance & Emphasizing Internal Character
Fair isle, pinstripe, and cowboy boots might not traditionally go together…but perhaps it would for a cowboy who decided to get a little preppy and yuppie.
As I’ve shared before, Forced Versatility is the concept of wearing something “incongruous” with a certain genre (or genres) and making it work as a part of a personal narrative. It actually operates on a similar approach to the “following the script” example I shared earlier, but in an internalized way that only manifests through the shoes. In this practice, the “final word” of the outfit isn’t a coda of what you’ve already stated (such as playing ivy straigh with pennys with ivy), but rather an opportunity to state who you are, especially when your outfit is made up of a few different things. In other words, a nuanced outfit is where the anchor function of footwear truly gets to shine.
Let’s have an example. A guy wearing leather oxfords with a suit and tie is playing it straight. But a guy in a suit and tie and cowboy boots certainly has more to say. Cowboy boots are rugged and sleek due to their heel and long shaft that goes all the way up, but they are also western. Wearing them points directly toward that context, even if the rest of the outfit isn’t fully western. After all, in states like Texas, people wear cowboy boots with everything as it’s a part of that heritage; people from such states often keep wearing them even when they’re not in that state anymore.
So because anyone can wear cowboy boots now (Apparel Arts even has a few illustrations suggesting you wear them), which means that we can wear them to leverage that western vibe (or semi-equestrian) and add something more to an expression than just being “casual”. To me, their inclusion in a fit shows that the “base person” is western (or at least likes it) and is keeping that theme alive through their shoe choice. A pinstripe suit can feel quite yuppie…until it’s worn with cowboy boots. The outfit is perceived differently. This western character is anchored by the shoes.
A menswear guy may want to wear a vintage tee and military fatigues but keeps his “menswear-ness” by wearing tassel loafers. You can see this vibe turned up to 11 when done with slippers or opera pumps by guys like Ethan Newton and Tony Sylvester. A streetwear enthusiast may wear a wool suit but reinforces his ties to casual-ness alive with New Balances or Salomons. The vibes can also be more vague as well. Paraboots with a suit can feel a bit Alpine; sandals and a suit point toward a summer context, even if you’re wearing a tie.
All of these fits would have been perfectly fine with other choices, but it’s about picking something with discernible character. Personally, I try to keep something thematic through each fit so that the shoe choice still feels natural rather than abrupt, which ultimately means a nod to formality if not a character, just to give some narrative direction. So while a chambray shirt, wool tie, or chore coat aren’t exactly western, a cowboy boot gives it a western spin without having it come out of nowhere. In effect, the use of cowboy boots creates a Thematic Variation of your other western fits!
As every shoe is connected to something, the “right one” helps you double down and anchor exactly what “character” you are, helping frame how the rest of the outfit is perceived.
Ethan Preferences
Lace-ups make the most sense with 1930s attire. Especially if its suede!
Though it goes without saying that there is still a lot more at play! It’s impossible to try and distill an entire shoe philosophy into something succinct. A lot of what I said here (and across the blog) is based on the expressive connections I’ve gathered through my own observations and experiences. This is where it gets personal, taking the process of picking the “right shoe” from a formula or cosplay guide to something instinctual. That’s why I’m sure many of you will have your own approaches. And to me, that’s the best part of this: menswear is about expressing your taste and shoes are certainly a big part of that.
For example, I like simply like suede footwear when it’s fall/winter, especially when its a suede lace-up. There’s something about sweaters and flannels that makes suede much more suited to those seasonal outfits than spring/summer ones (when most menswear guys like to wear suede). This could be a texture thing, but I also think its because so many “country” outfits (especially ones in Apparel Arts) showcase suede with such attire.
On a similar note, I also like wearing suede loafers with contemporary menswear outfits, especially when it’s something inspired by Jake Grantham and his brand, Anglo-Italian. If you’re familiar with him, you’ll know that he’s addicted to wearing suede footwear with his attire, even though his palette and garment combinations are pretty conservative. So when my outfits are a bit of a send up to his style, it’s nice to continue the reference with suede footwear. I’ll even wear suede with plain worsteds; I don’t need flannel or texture to find the need for suede.
If I wear a brown suit, I’m almost always in black shoes. It anchors everything down!
But fun taste “guidelines” aren’t always about Cinematic Dressing; it can also be a about a preference in color and design expression . For example, I tend to just prefer dark colors across the board, as they help me in my anchoring approach. That’s why so many of my shoes are black or dark brown (or color 8). I perceive that gravitas to be mature, helping me rein in my Esquire Man-approved triple pattern mixing or to double down on my minimal, Armani-inspired looks. Dark shoes are also preferred when wearing spring/summer outfits, where I always feel like I need to anchor such outfits’ light tones. And in general, I like wearing black shoes with brown suits.
I also prefer almond shaped lasts rather than ones that are too round/stubby or too sharp. There’s just something about that silhouette that I find elegant and versatile, which I find works perfectly with my preference for wide legged pants. My adherence to this taste allows me to wear almost any shoe in my closet with both casual and “formal” (tie-wearing) outfits, leaving the specific choice down to simply what POV I want to express that day. Other elements like low toe-spring and low vamps also apply here as well.
Of course I own shoes that don’t necessarily follow those preferences, such as my LHS penny loafers which have a much rounder toe than my full strap pennys (almond last). As a result, I see my full straps as an elegant loafer that happens to be ivy whereas the LHS is the straight forward ivy one that is more casual. I guess I can’t escape my character-based choices!
There are also my wallabees that are certainly shaped differently than my other lace-ups, which are usually worn to send up 70s casual vibes or more contemporary pairings (as they are remain popular as an “in” shoe, similar to Paraboots). Though that being said, I can’t deny that at times, I wear wallabees based on their blunted, soft appearance almost like a chunky slipper that you lace up (I guess I’m referring to a moccasin). That expressive property is interesting to leverage!
Leveraging silhouette is also the main reason I’ve enjoyed wearing boots, specifically my side zips and cowboy boots. In addition to pointing toward specific aesthetics or eras, like the 60s-70s, they also have the a sleek appearance through their lack of lacing, long shaft (lol), that is emphasized with a taller heel. This makes them elegant and sexy without the dainty-ness of a low vamp loafer. It’s a more rugged or masculine way to approach ease. That’s why some outfits, like ones with a flared leg, just make more sense with one of my boots.
Tassel loafers are my favorite and my dedication to wearing them across a variety of outfits is a big part of my Personal Style.
All of this is instinctual because I’ve spent time figuring out which shoes are foundational for “Ethan Style”, or select groups of Thematic POVs that I feel are authentic to my life and my taste. Picking the “right shoe” is easy when you’ve curated a hearty collection of footwear that reflects those qualities. At a certain point, there isn’t room for footwear (or any garment) that you seldom wear. Everything you own should help assist you with executing your POV, whether its through your favorites or your self imposed limitations.
You guys know that I tend to wear tassel loafers (and loafers in general) almost all the time. They are truly one of the main tenets of my wardrobe, being the “Ethan choice” for nearly any genre of outfit. I sometimes find that when I’m wearing an outfit but don’t feel like playing it straight or getting too subversive, I bring it back to tassel loafers. In other words, wearing tassels anchors an outfit as firmly “Ethan”.
I guess I’ve always been enamored with their design, especially when its almond shaped and has a low vamp. They just balance a trad theme with inherent elegance and slouch, serving as a great anchor for my base vibe. Don’t get me wrong; I also authentically enjoy the designs and vibes of my other shoes and so wearing them is still very “Ethan”, but tassels are my root, my default (in a positive sense).
And since they skirt the line for formal and casual, both to me and other people, I’ve realized that I don’t need a black or brown oxford. A tassel loafer can do it all for me! In fact, the onlyblack lace-up I own is a thrifted pair of split toes derbies that are nearly a match for Paraboot Avignons. While they would be fine with suits, I like wearing them with separates, such as military or work pants, since those shoes naturally work with those types of fits (also that’s how people tend to wear Avignons). They also look good for French Ivy.
All my other lace-ups are brown and are usually casual, as that list includes my pebble grain paraboots, camp mocs, and handful of suede shoes like my Armoury split toes, my brown cap toe brogues (my only oxford), my chukka boots, and my single monks. [The latter three are ones I’ve owned since college!] I tend to wear them (and lace-ups in general) as such, being used when I don’t feel like being a dainty little boy with my low vamp loafers. If I want to keep the “elegance”, then single monks are the move. The oxford is for the days I want to be formal and more traditional; the split toe is for the in-between days. Camp mocs are when I want to be casual in a way that points to milsurp, workwear, or the outdoors without wearing boots. And then as I discussed in its own blog post, Paraboots are a great mix of rugged, artsy/weird, and contemporary; my POV or Theme helps guide which one I want to emphasize.
I also have other fun footwear such as my fisherman sandals, opera pumps (crazy eBay find), and my Aurora mary janes “sandals” (flea market). While not all exactly loafers, I find them similar in their slouchy and elegant vibe, which is how I wear them all with ease, across formal attire as well as ones that are bold in general (like Safincore). It can be about playing a look straight (black tie) or about anchoring a type of slouchy (or dainty) character (opera pumps with a suit and tee shirt).
There are obviously a lot of shoes in the menswear canon I don’t own, but at this point, I don’t think that I need to own them. I’ve already found the “right shoes”( or rather a collection of the “right shoes”) for the types of outfits I want to make. I love all of their expressive merit and the character that they bring to the table! And as a result, it’s so easy for me to pick what shoes I’m going to wear that day.
Yes, there are some compromises that are made when I don’t have the specific shoe that a look may “require”, but I always find that my existing wardrobe comes in clutch. I don’t need an SLP black jodphur because my black cowboy boots serve me just fine. In fact, the cowboy boots are perfect not just because they are also sleek and heeled, but because they are tied to Vintage Americana, which is one of my core interests; it also makes sense considering my outfits, even the Going Out ones are a bit more “rugged” than a typical SLP look anyway. So even if they aren’t the “correct” shoe in terms of tradition, they are still the “right shoe” for me.
Conclusion
We all have our own way of picking the “right” shoe for our outfit.
There’s so much more we can say about this, which is why Spencer, MJ, and I discuss it on the podcast below. Since Spencer and MJ both have their own unique collection (MJ especially deviates from a trad wardrobe), they provide even more insight into how they think about shoes and how they ultimately pick the “right” one for their chosen outfit. We also get into things like weather (or what passes for weather here in LA) as well as our little idiosyncrasies found in our taste and expression.
For example, none of us believe that shell cordovan is more casual than calfskin, despite what trad menswear will tell you (this is also a way to tell myself that I don’t need to buy more shoes for the sake of material). I also reveal on the pod that I tend to wear lace-ups whenever I wear hats like fedoras and berets. Since hats are used to shield yourself from the elements (like when it’s raining or when it’s cold), it doesn’t make sense to wear footwear that reveals your feet. Little preferences like that can only aid you in picking the “right” shoe for an outfit.
That’s what this is all about. The goal is to ultimately make the decision in picking the “right shoe”, as well as any other garment,” be an easy one.
I know that this was a long blog post that makes it seem like there is so much thought and effort involved, but believe me when I say that this is instinctual and second nature! It never takes me a long time to pick a shoe to wear nor do I ever regret the shoe I walked out the door with (though I may have felt like this at the end of a day filled with walking lol). This was only long because I wanted to write it out and codify it so that it may potentially help someone reading this…or at the very least understand how my mind works.
Above all, I believe that we should strive to be aware of what we aim to express, as well as the expressive merit of our garments. And when it comes to shoes, the “right” one should ground your POV, serving as an expressive capstone to a fit. It doesn’t matter if the shoe itself is bold , understated, formal or casual. Even if it only takes up a small amount of “real estate”, a shoe is a great opportunity to double down and emphasize exactly what you are trying to “say” with your outfit.
[End of blog post]
Podcast Outline
10:41 – Topic Start
14:27 – How Important are Shoes?
27:45 – How Hard is it to Pick Shoes?
34:17 – Shoes can’t Make/Save an Outfit
42:16 – How We Pick and What We Like
1:32:37 – Outro
Photo Time (there’s a lot)
Shoe choice is just as intentional of a choice as our jacket, shirt, pants, and socks.
Each one is full of context and expression to leverage.
And even though many shoes in menswear can be worn across different formalities and outfits…
…we can’t deny that each one has their own character.
They assist us with the “story” of our outfit, contributing to and even emphasizing the theme we want to express.
It will always help to figure out what your POV is.
But when it comes down it, we all express things differently. Like being casual…
…or getting a little slick when we Go Out. So it’s funny when we try to express the same thing with different shoes…
…or different vibes with the same shoe.
Three similar outfits all with different shoes!
Look at how Chris wears his wholecut loafers! They slightly subvert the ivy theme of his fit.
He then does it in a relaxed way with a terry cloth shirt and chinos.
Jay has the same shoes and tends to wear it with slouchy tailoring.
We all have our signatures!
James loves his black heeled boots. They bring a sleek 70s vibe to everything he does.
They even help make a cardigan fit feel quite Husbands.
Of course it’s interesting to note that when he really wants to dress down, he wears converse…with the garments he typically wears. Talk about Forced Versatility!
This whole thing is about taste, our preferences. Would you wear oxfords with chinos? Cody Wellema would!
Or brown loafers with black jeans?
Your shoe choice will always say something.
It speaks to what “character” you are, what narrative is happening. Travis Bickel does the interesting move of wearing cowboy boots with jeans and a military jacket.
Vibes can always be played straight, like wearing pumps with evening wear.
Or they can be subverted to whatever degree you like. Here, Cary Grant wears penny loafers with a tux. Incongruous, but it does communicate something!
Shoes can provide contrast and anchor the tones of your outfit…
Or can play along with the tones.
A tweed jacket with white bucks? How interesting!
Fun summer ideas here.
Two-tone suede shoes for fall!
It’s always about what look you want to go for. Mark could have worn any pair of shoes here but he went with penny loafers to anchor in the ivy vibes of his overall fit.
Some pairings are rooted in formality, but that makes them ripe for subversion. Menswear traditionalists say oxfords aren’t meant to be worn with separates. But Bruce Boyer does it quite a bit!
It also makes it interesting when he doesn’t wear oxfords.
Most of the time, its nice to follow the “rules” since it makes shoe choices easy. Wearing a 3PC suit in a dark color? Black oxfords it is!
Oxfords just have that vibe.
But again, its fun to see when people forgo oxfords and opt for something else, like tassel loafers!
Or when they double down on oxfords.
Oxfords with a suit…and polo shirt!
Kamoshita-san wearing oxfords with separates. Perhaps suede is key here?
I always loved this photo of Mark wearing suede oxfords with a tuxedo. Feels quite Esquire Man!
Or what about how different people choose to wear black shoes?
Do you like to wear your pinstripe suit with brown or black shoes?
Black shoes with brown suits is a popular choice
I enjoy the gravitas it provides.
Its also nice to play it straight and wear black with black. Makes things easy!
Sometimes things can be incongruous, but then it starts to make thematic sense the more you think about it. The loafers here anchor the trad menswear-base. If Shinn wanted to emphasize the overalls, he might have gone with engineer boots or sneakers.
Loafers with this fit reinforces this as a “menswear guy who loves metal”.
Makes sense coming from guys who wear a lot of tassels already.
Newton even does loafers when layering up!
Velvet slippers and double denim is an interesting pairing, but it makes sense for who Ethan Newton is.
And now slippers with everything is a discernible Bryceland’s move.
Playing it straight is also a good move. Jeans and sneakers are good friends!
Just like oxfords and 3PC suits.
But mixing it up is where the fun lies. Our adherence to our preferences is makes personal style!
Shoes are more than just formality or utility; it’s about expressing a character and showing narrative or thematic decisions!
I like how this sleek Sexton suit was paired with a mid-brown penny loafer. Convention would say to at least wear this with a boot, but I like the choice! The pennys make this feel a bit more “trad”.
Stephon wearing huarache style shoes help emphasize this vacation-inspired attire.
Sandals in general have that effect. Most of the time its worn with super-casual attire.
It’s a “subversive” move that points toward an inner appreciation of elegance (whatever that means) but also characterizes a bit of the NYC menswear subculture.
Tony Sylvester does his own “high low” by going very rugged and casual with the clothing and then going very formal with the opera pumps.
Our choices and preferences end up being a signature, much like Ralph and wearing jeans and cowboy boots with tailoring.
Its one thing to wear jeans with a sportcoat and another to double down with jeans and cowboy boots.
It really helps point toward Ralph’s POV.
I mean cowboy boots just have such a strong context that is easy (and fun) to leverage! Chase does it well here.
These are Ropers but thjey still provide a western anchor point to an otherwise ivy outfit.
The cowboy hat and cowboy boots help end-cap the barbour and bengal stripe shirt.
Our choices end up being a signature, like Jake (and Anglo-Italian) and suede loafers.
I like how the shoes (a cool take on horsebits that aren’t too crazy) help the fit make a nod to menswear.
Sneakers with trousers are cool vibe!
Its an intentional narrative choice!
Even though there’s a tie and sportcoat here, the sneakers emphasize just how casual this is meant to be. And with the ball cap and vibrant jacket, it plays into intentional youthful vibe of the outfit!
Things can just be fun too, like wearing animal print paraboots with a relatively monochromatic base (though the plaid coat does match the shoes).
The horsebits function simialrly here, with the hardware being a visual contrast to the plain outfit.
Suede shoes always point Esquire Man to me.
They call them “buck-skin”.
Its a bit of a sporty and dandy shoe choice that is definitely apart of this Theme.
Or when its rugged sole but worn with largely trad tailoring.
No matter the size of your collection, picking the “right” shoe for your outfit is all about figuring out what you want to dress as.
We have so much menswear history and precedent to leverage.
Shoe choice definitely says something about your POV!
I like how Ivan wears black chelseas with a 1930s suit. As was the case with James, it points his fit to the 1970s.
Even if he’s in a tee shirt, the heeled boots play into the slick vibes of the dark pinstripe jacket. Wearing this with sneakers would have made for a totally different look!
Sam wears black cowboy boots with a guncheck jacket!
Husbands uses footwear to great effect. Using sharp, cuban heeled shoes help show that their “office” themed fits are still quite chic and pointed into their aesthetic.
It’s the “right” choice for Husband’s.
I love that even though they did a very casual (and tonal) outfit, they kept the black boots. It keeps the fit firmly anchored in their base POV.
Saman Amel uses suede shoes in light tones to emphasize their minimalist and earthy POV.
The “right” choice for them is about not having much contrast. Also the suede plays into the “plush” aesthetic that Saman Amel has.
It reminds me of Danny Kaye’s grey canvas oxfords that match his suits color exactly. (Its a black and white photo but watch the actual clip).
Kamoshita-san pulls a similar idea here, as his black suede oxfords help anchor the charcoal plaid suit, allowing the purple tie and lavender shirt be the focal point.
But contrast is fun too!
Marco is an expert with shoe choice. Here, he has chunky, black Tyrolean shoes that help anchor his slouchy chore suit.
His colorful-sneaker boots contrast against the loose nature of his outfit but are a great match for the colors!
Of course some pairings are just based on his own instinct and taste. We can learn a lot from him!
Tyrolean shoes with a crop top? Genius!
He also likes to play things “straight”, like wearing engineer boots with a leather riding suit.
And like the rest of us, Marco also has a favorite type of shoe that he wears across a lot of his outfits: clogs.
They’re clunky, slouchy, contemporary, and different. Perfect for Marco and his style!
You gotta love how often he wears them!
MJ has just as much fun with shoes as he does with his other pieces. He has a soft spot for trad loafers (like pennys)…
…but he tends to also like fun shoes (like the 2120 wholecuts that a love of our pals also enjoy).
He also has some clogs, which certainly tie his fits more to the Zeitgeist.
But if he had a favorite, they would definitely be paraboots!
They’re “dressy” in the sense that they are a leather lace-up shoe that sorta looks like a typical derby. However, they are chunky and rugged, which makes them a fun choice with Vintage Americana.
It also works for MJ’s slightly-gorpy attire.
It’s even good with his own take on Safincore, which leans more rugged (thanks to his shoe choice).
Other guys may pair a workboot with an A-2 and chinos, but MJ goes with Paraboots!
Its definitely a signature for him.
This is one of my favorite looks from him. And the shoes definitely play a big part of it!
Spencer definitely uses his shoes to play into the vibes of what “character” he’s dressed as. A GI back home would most likely be wearing canvas sneakers with his old chinos and fatigue jacket.
Its usually a no-brainer to wear sneakers with casual clothes, but I think you can tell that Spencer has some method behind it, especially since his casual attire has a specific look.
This would be a nice ivy fit if worn with penny loafers, but he goes even more dressed down with his Converse. It also provides more bit of visual contrast compared to a color 8 loafer.
What I think is interesting is when he wears a sneaker when other guys may have picked a boot. In effect, it makes Spencer’s look feel “softer”and more at ease, which is exactly what he’s going for. You’ll note that here, Spencer played into the faded indigo of his chore coat and jeans with his very well-worn deck shoes.
Also interesting to wear sneakers here when a the overall fit is more Western or Workwear (aka boot outfits).
Another outfit that feels a bit “subversive” with his choice of deck shoes over leather shoes.
Spencer’s use of sneakers is one of his signatures.
He throws them on with everything!
And its good.
That being said, he does actually wear leather shoes, especially when they’re lace-ups. He rotates between derbies and oxfords and wears them whenever he wears a sportcoat.
Longwings feel ivy and Spencer certainly wears them that way.
Oxfords with a sack suit!
It just makes sense to wear a lace-up with a jacket and tie.
When he wants to be slightly dressed down, he wears an old pair of split toes. They’re chunkier and less streamlined than his longwings/oxfords but that’s the beauty of these split toes. Spencer wears them quite a bit!
If MJ likes his Paraboots, then Spencer likes his split toes.
They’re good when he wants to wear a leather shoe that isn’t too casual/rugged or too formal.
Of course all of that makes it quite interesting when Spencer does decide to wear loafers. It certainly makes for a different spin than his typical combinations.
It definitely makes his typically rugged and “hard” style (lol) point toward classic menswear (which is “soft” in my weird brain).
Crazy cool use of tassel loafers with this fit!
The use of penny loafers here makes this feel like an ivy-guy going western instead of the other way around. In other words, it reinforces that ivy was the base theme for this outfit.
However, it seems that ever since Spencer found some cowboy boots, he hasn’t been able to stop wearing them. Not only do they make sense for a lot of his outfits, but they make sense for him!
They obviously help make anything he wears feel western.
This outfit is generally casual and workwear-y…but it goes western with the boots.
Its also perfectly fine for a sportcoat and fun swing tie!
It’s also a shoe a guy would wear in the 1970s.
They’re always the “right” shoe for Spencer.
Ethan’s Turn! Playing It Straight
Picking the “right” shoe is often an easy choice for me as every look has a natural pair. For example, an ivy-esque suit with ivy accoutrements (OCBD, repp tie, tv-fold pocket square) is traditionally worn with penny loafers. And that’s what I’m doing!
Tassel loafers are great for general menswear.
Do it in black when you want to be formal, such as when you wear a grey suit and a black tie.
Suede tassel loafers help send up Jake Grantham and Anglo-Italian, especially when you’re in a grey suit and club tie.
Lace-ups, especially suede ones like these oxfords, are great for Esquire Man and other Golden Era inspired looks.
In fact, you’ll notice that many of my overt vintage-leaning outfits are worn with some type of suede lace up.
They just feel “right” to wear in fall/winter, as their closed up and cozy nature help me lean into sweater vests and tweed jackets.
Overall, it would be weird to wear loafers with this fit. A suede boot just makes sense thematically for the look I’m going for.
It’s the same reason why I wear penny loafers. I don’t think of them necessarily as a casual shoe, but an ivy one. It was fun to wear them with a blazer and tattersall waist coat.
Or with some GTH pants.
Any shoe would’ve been “fine” here, but the penny loafer firmly plants this look as a send up to ivy.
Madras pants? Penny loafers!
I truly think that every time I wear a button-down collar, I’m also wearing penny loafers. It just makes sense!
Of course you can take an ivy fit and point it toward Drake’s (or contemporary) with tassel loafers instead of pennys. Though you can’t forget the purple socks!
A lot of these preferences are internal, but they are a great guide. I felt like this outfit was a bit 1980s office guy, so black tassel loafers were the way to go. They help anchor the formality and also play into the look.
Black horsebits help affirm the 1970’s vibe I’m going for.
The shoes help send up yuppie vibes in this one. I also find that the metal echoes the cream dots in the tie!
As I said before, I only have one black lace-up and its not an oxford. However, it still looks fine for traditional “dressy” looks where a loafer might be too elegant as a choice.
I’ve noticed that I wear my leather lace ups when I want to feel conservative.
Its a subtle choice but one that helps me get into the spirit of what I’m wearing.
They also feel ivy and “rugged” but without resorting to Paraboots. Derbies and bluchers are fun in that way!
I wear suede shoes when I want to play up “country menswear”, which includes fall/winter layering, Esquire Man, and English-trad.
The soft texture and “closed up” nature of lace-ups just feels cozy, which makes sense for them to be worn with layered menswear attire.
They also feel pointed toward vintage, since they aren’t exactly an “office shoe”, traditionally speaking.
That’s why I wear suede lace-ups with pattern heavy Esquire Man outfits. The suede plays into that vibe!
I also like wearing hats with suede shoes. They work together to act as end-caps to the outfit’s Theme, almost like the bread of a sandwich.
And as I said before, I also like wearing suede shoes (specifically loafers) with my Jake Grantham/Anglo-Italian themed outfits. They often add some interest and softness/slouch to an otherwise [delightfully] austere outfit.
Suede tassels make this fun rather than corporate. If I wanted to send up the salaryman vibe, I would’ve picked a different shoe!
Speaking of fun, I’ve also enjoyed wearing my white buck penny loafers! They’re perfect for going fullprep.
I’ve also liked wearing them as a nod to swing/rockabilly outfits. They’re just a part of that specific look.
Wallabees are in that same vein, being used to reference an alternative (but still accurate) version of 1970s ivy. Its a no brainer!
Played Straight With Casual Attire
My casual looks also have a guideline of sorts, which makes picking the “right” shoe easy. When I wear western looks, I wear cowboy boots. Easy!
It doesn’t matter if the jean is a bootcut or not; the cowboy boots anchor in the west.
I also wear them for the “off duty 90s movie star” look. So even though I’m not sending up a specific western vibe, the cowboy boots are still a part of a dedicated POV.
But for me, I think I really enjoy playing it straight western.
I also have black ones, in order to provide a sharper contrast to my pants and achieve a sleek look.
They also work for general 70s attire.
Side zip boots are similar. With their more minimal design, they’re the “right” shoe for a sleek, Going Out look.
Desert boots are worn when I want a “softer” approach to boots. They’re still boots but they aren’t as sleek or sharp, which is great for when I do more of a workwear-tailoring mix.
I’m not going for a cowboy or 70s look here. I wanted something more “1940’s casual” which is why the desert boot was the “right” choice.
And when I really want to play up the ruggedness, I’ll wear my Danner boots.
They’re great for a hiking aesthetic (for both fashion and when I’m actually using them).
They just make sense for this type of look.
Sneakers are also the “right” shoe for most of my especially dressed-down looks, where its about sending up vintage casual attire. Like Spencer, I also like dressing like an off-duty GI by pairing Converse with fatigues and an aloha shirt.
As I said before, I like sneakers because they’re not only casual, but they have a “soft” appearance, especially compared to my typical dress shoes (or the expected boot).
I wear them a lot in spring/summer.
I also like the look of soft sneakers with my full trousers.
When I want to get a little more rugged and point to menswear, I wear my camp mocs! They’re not a boot or a true dress shoe, so its a good in-between shoe that feels very sporty, at least by 1940s/50s standards.
I enjoy when I bring them out.
They especially look good with shorts!
But they also just make sense to wear with layers. A loafer in fall can be a bit odd, but these casual lace-ups work!
I think that my leather jacket fits tend to always have some sort of lace-up.
A lot of this is predicated on my preference of wearing lace-ups with overly casual and rugged things, like hearty selvedge jeans.
Paraboots also fall into this casual lace-up category but they have their own pairings and guidelines.
When I really want to be casual, I’ll wear my mary jane sandals. They’re “soft” and slouchy, but not exactly elegant. They’re great for Safincore.
The sandals look and feel quite cozy.
Of course my B&L Sagans are the opposite of the sandals, being a Belgian-esque slipper in a sleek black suede.
Instead of looking comfy and lazy like the mary janes, these have an air of elegance to them. If I want to play up grace and sophistication, I’ll wear the Sagans.
Sandals work here as well, when I want a bit more air flow.
Opera pumps are similar to the slippers and sandals, but I tend to wear them with black tie.
Shoes For Color & Contrast
In addition to being a part of a “look”, shoes also help me anchor a fit. This is done by simply being a dark focal point of the fit, to provide visual weight. This optional, guiding philosophy is why I prefer dark shoes.
I love doing it like wearing color 8 with a white linen suit.
It just looks so cool with khaki.
Black does really well too. Not only are the shoes heeled and sleek, but they’re black.
I just like strong cohesion between my shoes and my trousers.
Though contrast works too! I just find that dark shoes help rein it in.
That being said, there are a few times where I don’t go for contrast. Wearing brown shoes with brown trousers feels “soft” and easy.
It feels nice!
Suede certainly helps in that regard.
I’m definitely playing up the brown tones in this outfit.
It’s fun to lean into every once in a while!
Black shoes would have been too dark and fashion-y; the brown suede split toes help make it more at ease.
I do prefer to wear brown suede with Esquire Man.
Its just fun to lean into the tones instead of contrast. That makes these suede derbies the “right” shoe!
But you guys know I also love black shoes.
Since I wear a lot of brown, I use black shoes to be the “anchor” and provide contrast without being loud.
Brown loafers would have been expected for Ivy, but black is a chic choice.
Brown cowboy boots would’ve been fine here to make things casual and rugged, but black provides a different vibe and more contrast.
Here, black tassels provide gravitas to the fit despite the vibrant shirt and tie combination.
When I do something tonal for the main outfit, I like wearing black shoes.
It just feels right.
It works even when the monochromatic tones are on the lighter side!
I do it whether I’m casual…
…or “formal”.
Of course, black shoes also help anchor things when I have some fun with color.
Whenever I wear “bold” pants, I tend to wear black shoes!
They just help keep things serious. Or at least as serious as I can be!
And when I want to be elegant, black just makes sense.
When colors get muddled together, black shoes jump in and anchor it all down.
White bucks do a similar job in the opposite way, providing contrast and vibrance to any fit they’re worn with.
It’s fun to do a look that would have normally had black shoes…and do it with the white bucks.
Though most of these white buck looks are often pointed toward summer, which makes their choice motivated not just by color but by overall vibe.
Then again, I also like doing low contrast, tonal stuff with my white shoes.
Its a fun thing to lean into every once in a while, when it just feels “right”.
While a dark shoe might have added some gravitas to this fit, I like that the white sneakers make it come across as “soft” and easy.
Its a similar story here, though much more casual due to the white tee shirt.
I also like pairing the white bucks with my khaki suit, for similar but more restrained overall look.
I also occasionally use my wallabees in the same way.
Shoes To Anchor The Intended POV
Of course the best part of this is nuance or when you either affirm or subvert your own tastes. It doesn’t have to have a large effect, like how a suede tassel loafer takes the ivy root of this bowtie fit and gives it more of a #menswear spin (to me at least).
A suede desert boot not only contrasts with the grey, but it also helps move away from the corporate connotations of the suit and play into the “casual” items like the sweater vest, checked shirt, and club tie.
Some outfits simply have fun with shoes!
And others fits just use shoes to double down on the POV.
Here, penny loafers help give this look an ivy nod.
Same goes here, though penny loafers are already inherently tied to the school boy look.
Horsebits are not just yuppie— they are also quite popular in Japanese Menswear circles, when you wear a tailored jacket with fatigues! It’s a part of that look.
Horsebits also help emphasize the base 80s/90s tonal suit vibe even when I’m wearing a kimono coat.
Suede tassel loafers point me toward #menswear, even if the outfit is more trad.
This would’ve been fine with penny loafers, but I went with suede tassel loafers!
Even though an aloha shirt and full cut trousers can be vintage, the use of a suede tassel loafer brings the fit to a contemporary context.
I do this exercise often, especially when I’d find a lace-up too hot to wear when its sunny!
Though sometimes I just like to wear it.
Again, it will always feel a bit #menswear. I like to double down on that from time to time!
Wallabees help affirm a 70s vibe.
They take up such a small amount of real estate, but the effect is there! That’s the power of picking the “right” shoe.
It also feels quite contemporary. I love it with a tee shirt and suit.
I like that they help point me in a specific direction.
And its usually something a bit zeigiesty or at least more contemporary.
Its fun to wear!
A different vibe from wearing horsebits.
I also find wallabees a little artsy and comfy due to their plush appearance.
Again, its fun to lean into. It’s all about deciding what you vibe you want to do.
In that way, its about anchoring a look. Loafers or a derby would’ve been fine here but cowboy boots plant this firmly as western.
The side zip boots help push this as a Going Out look and not a vacation look.
Boots, whether they’re side zips or cowboy boots, have so much character to leverage.
This one is a no brainer!
This could be a bit of a random fit of fun things worn together, but the boots state the outfits’ western theme.
Same goes for this one!
Sometimes its obvious…
…and other times a little less so (because of the beret).
Cowboy boots are also a bit contemporary, so they can also help point your fit in that direction.
This one isn’t western or super 70s, but the cowboy boot still feel like the right choice.
However, most of the time I think the intended theme was apparent from the start.
Paraboots are also loaded with context.
In addition to being a rather funky shoe, they also feel quite Drake’s.
They also feel a bit Alpin and European Apparel Arts.
I like to wear them when it rains.
As I said before, they also feel quite contemporary (thanks to the Zeitgeist), so I like leveraging those vibes when I dress Vintage Casual.
This is a very 70s Marvin Gaye fit, but the Paraboots place me back in the 2020s.
So when it comes down to picking which one is “Right” for the fit, you just know. This could have been Drake’s with the Paraboot, but I decided to go more “normal” with the camp mocs.
But there’s nothing wrong with getting inspired by Drake’s!
Some schoolboy looks are good with blucher mocs…
…and Paraboot with others!
Longwings are more “normal” than Paraboots and are also a pretty conservative choice. So here they affirm the vintage 1940s vibe without going too western.
They also help anchor down this slightly wild preppy fit.
Black lace-ups are good for French Ivy.
Again its all about vibes and character. The sneakers in this fit help emphasize the slouchy ease.
Sneakers help reinforce how casual I want to be, both aesthetically and mentally! This would’ve been fine with loafers but a deck shoe is the “right” choice.
While the vest is workwear, the sneakers work with the madras pants, OCBD, and bucket hat to play up the base character of casual-prep.
Sneakers instead of loafers here makes this feel plush and comfy instead of elegant. I like that!
Not every menswear fit has to be a loafer one!
Sandals have been great to swap in, to give it even more of an at-home vibe.
Fisherman sandals play up the elegance, making a rather casual combo (tee and suit) look artsy.
My shoe choice helps me emphasize the POV that I want. This definitely has a bit of a home-garden vibe.
This feels a bit rugged and artsy but the sandals say “comfy”.
My slippers help me emphasize that this is meant to be a version of Black Tie, even if they (and the cummerbund) are the only true black tie pieces in the outfit.
Wearing opera pumps with casual things plays into the days when I feel like a Dandy.
Though I think my favorite “middle ground” has been my black fisherman sandals. Due to their design, silhouette, and color, they’re fantastic to wear across different POVs.
A Very Ralph Look…but with sandals.
They help play up the summer vibes in a way that loafers just can’t.
It probably makes the most sense to wear them with open shirts and slouchy suits.
I certainly do that often.
But I also like what it says when I wear them with a jacket and tie.
Or when I wear them with socks!
Wearing them with black tie is going to be a common thing for me, especially when its warm.
Tassels
But when all that is said and done, my signature shoe (if you can call it that) has to be the tassel loafer. I wear it all the time, even if its not exactly what someone would wear in the 1930s/1940s.
They inherently tie me to my central POV of just being a menswear guy. Even here, when I mix a sawtooth western with a pinstripe suit and kimono, I’m still wearing tassel loafers.
They’re just so easy to slip on. I can make them feel casual…
And they’re good with a tie!
Open shirts…
…no jackets…
…and even with Safincore!
I wear a tassel loafer most days of the week! I wear the black ones…
…the suede ones….
…and of course my beloved Color 8s.
Because even if I’m dressed in a 1930s Apparel Arts way, I want to bring it back to Ethan. And that means wearing a tassel loafer.
Doesn’t matter if the outfit is a little dandy…
…or conservative.
When the POV is meant to be “Base Ethan”, I wear a tassel loafer.
Because in the end, the “right” shoe will always be the one that emphasizes exactly what character you want to express. Of course when you want to express multiple things, you may find that you’ll need more than just one style of shoe…
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