I’ve said it before and I’ll say it again: going Full Send is the best way to get dressed.
This approach brings together two major tenets of my clothing philosophy: we should use the coded themes found in clothing to our advantage and to always dress with an intentional POV or character in mind. This is incredibly easy to do with elements of classic and vintage menswear. White and brown suits often feel “old school” but also express different things (vacation/summer and country/rugged respectively). OCBDs are ivy while spearpoints are 1930s-1940s. Full Sending simply means to fully invoke the themes (or semiotics, if you’re feeling pretentious) in our outfits.
For me, going Full Send has typically meant to dress in a way that feels creative. I do not mean in terms of breaking boundaries but in terms of showing off a creative spirit. Typically this does invoke ivy or trad in some sense in a subversive yet slouchy way. But as I look back at my menswear tenure, it’s also clear that I’ve had the hankering to be more than that. Going Full Send here means to put slouch aside and instead, posture a bit more severity and power.
I’m talking of course about the Chalkstripe & Pinstripe suit, a garment that imbues power within its stripes. It represents the epitome of going Full Send in menswear, being the definition of corporate attire. Leaning into it is all a part of the fun. And as odd as it may seem, it also somehow connects me with what it means to wear menswear, giving it a special place in my heart.
In that way, it also coincides with the other themes that have characterized the recent output of the blog: nostalgia and coming full circle.
It’s hard not to deny the appeal of Chalkstripe and Pinstripe suits.
First off, the stripes themselves are just inherently cool, their off-white or cream lines adding visual vertical interest to an otherwise “basic” suit color (brown, grey, or navy). They state the wearer’s presence with authority, the volume of which depends on the taste of the wearer. Pinstripes are quite striking but typically have a thinner line. Chalkstripes have a softer appearance but have a subtly bigger width. We also can’t forget that the spacing between the lines themselves also plays into the “voice” of these hallowed suits. In fact, this power ultimately makes them easy to wear.
Like a checked jacket. The inherent visual interest of Pin/Chalk-stripe contrasts smartly with other patterns, making it go with any type of tie; a quick look at vintage photographs and illustrations proves the “theory” behind matching. Scaling tends to be key here but most ties and shirts employ different widths, which makes triple stripes an effortless combination if you don’t mind the visual “complexity”. Even bowties (keep em patterned btw) feel natural to wear with one of these garments. Of course, solid accouterments are the ultimate no-brainer since plain ties/shirts/knits are enveloped completely by the Pin/Chalk-stripes.
The vibe is up to the wearer and their choice of base. SB notch is normal and trad. DB or SB with peaks certainly up the ante, rewarding your gumption for elegance as you lean into what the Stripes are all about. There’s also the color of the base itself. Stripes on navy and grey feel formal or corporate while using brown makes for a fun vibe on something seen as more “casual” (relatively speaking). These basic menswear semiotics provide prompts for subversion of leaning into. But as was the case with white suits and bucks, suits are more than just color and pattern. They have meaning!
It is obvious that Pin/Chalk-stripe suits are inherently coded thanks to their cultural history over the past hundred years.
Menswear media always shares that they are the de facto look for everything business, finance, and law, no doubt due to the power found within their pattern. We apparently have English bankers to thank for that, as it has been said that it literally was their uniform in the 19th century. It’s almost as if wearing the garment would give you that gravitas. This was adopted by gangsters in the 1920s-1940s as a show of legitimacy that ultimately “backfired” into becoming the classic look for such criminals, both in fiction and real life.
What’s interesting is that when we look at Apparel Arts and Esquire’s Encyclopedia of Menswear, striped suits were simply suits that were striped, picked simply due to their color coordination properties and visually slimming nature. It is true that they were seen as garments suited for the City rather than the Country (mainly navy and grey), but overall, Pin/Chalkstripe suits could be found advertised (and worn) next to plain suits and checked ones with pattern being their only difference.
Yes, you could see pinstripe suits styled conservatively with plain or silver ties (or the trad way with regimental stripes), but you could also see them worn slouchily (AA would call it “semi-sports” with boater hats and abstract ties. Hell, you could even see them worn as jacket or trouser separates with ease! They were indeed just another type of suit to be worn, proven with plenty of photos of movie stars and regular people alike.
To my eyes, it was the 80s and 90s that cemented the thematic identity of the Pin/Chalk-stripe Suit, particularly the ones with a grey and navy base (business colors obv). With the rise of corporate america and the casualization of mens dress, striped suits doubled down on being firmly for business, almost to the point of hilarity. In other words, suits in general were no longer an obligation but certain mfers (Wall Street?) leaned into the Pin/Chalk-stripe Suit. With the glory days of business attire far behind us, it makes sense for a Menswear Guy to want to send it up and relive it through wearing such a suit, whether or not they actually lived through that era. After all, the Stripes stretch toward the heavens, almost helping you reach the aspirational corner office on the 50th floor.
Even if we try to remove the corporate connotations of the Pin/Chalk-stripe Suit, it is apparent that the garment feels inherently “old school” or “vintage”. A Pin/Chalk-stripe Suit invokes feelings Nostalgia, business or not. Gravitas brings about agedness, which is exacerbated by rarity, as most guys tend to not wear them unless they want to. Seeing such a suit reminds one of old movie stars and illustrations where they were able to wear character exuding garments with ease because it was “just another suit”. In other words, wearing a Pin/Chalk-stripe Suit has the ability to send up the Golden Era even if you aren’t wearing a fedora or a pinned collar. This is especially true of a brown base variation (as it’s the most uncommon) but it honestly applies to all of them.
Despite its roots being a “normal” suit, it’s clear that today it is more than that. It is something to lean into and embrace, not unlike white bucks or a white suit. The best dressers (in my opinion) have always been the ones who send it up.
Ralph Lauren is a great example of that. You might even say that RL has made this garment a part of their signature look. RL has made the striped suit one of their iconic things, connecting the corporate themes with an aspirational and luxurious lifestyle. Old photos feature striped suits with polo coats and cream ties, providing slouchy drama and gravitas. However, pinstripe suits were also worn in a pseudo-English way, with contrast collars and club/motif ties. RL is also known for wearing striped jackets with white pants, which are also luxury-leisure coded, making Pin/Chalk-stripes look elegant and easy to wear at the same time. In the current world, it’s hard not to think of Ralph when a Menswear Guy wears a striped suit.
Of course RL isn’t the only one. Lots of menswear guys today invoke the power of the Pin/Chalk-stripe Suit. Arnold Wong inherently has a Golden Era charm with his bespoke DBs, seeing as they pair them with fedoras and geometric ties. Chad Park and Ethan Newton have done similar things with their attire, going between corporate and vintage looks based on how he styles them. Like I keep saying, striped shirts (as well as blue/white solids) and a patterned tie is simply the way to go with a pinstripe suit. It allows you to lean into it, making it quite easy to wear. However subversion is also recommended and serves as a great way to get the most out of such a bold garment.
Ethan Newton and his compatriots at Bryceland’s get interesting with their Striped Suits as they frequently pair them with western shirts. Quite a few NYC guys lean into the sleazy attitude the suit affords, wearing their Pin/Chalk-stripe Suits with vintage abstract ties (corporate 80s) or going casual with black button ups or white tees (a bit 80s/90s gangster). On a more subtle note, Jake Grantham utilizes stripes to evoke classic English attire but with his signature ease, combining the power of the Stripes with slouchy construction. To me, this balances severity with nonchalance. I especially enjoy the juxtaposition when he puts a rugged Barbour over his striped suits (instead of a dressier coat). All of these guys add expressive possibilities to the Pin/Chalk-stripe Suit while remaining in awe of its inherent gravitas.
In every case, it is about Full Sending the attitude of a Pinstripe or Chalkstripe suit. I understand that this can be intimidating and can scare off “newbies” who want to dress to simply look “nice” (which a blue or grey suit can certainly assist in). But once you’re passed that idea and you want to exude some power (even if its tongue-in-cheek), the Pin/Chalk-stripe Suit is alluring and easy to wear. It is for the day you want to be serious and edgy rather than slouchy.
And that’s what got me.
If you’ve kept a close watch on my menswear tenure, you already know that I’ve been in love with Pin/Chalk-stripe Suits ever since I started. How could I not! As you can tell, there’s just so much media, both vintage and contemporary, that provided ample Inspiration and stimulation for my outfits. It was only natural that I made sure to acquire it (and its vibes) to what I consider to be “Ethan Style”.
Some of my first vintage purchases were Pinstripe and Chalkstripe, though they were odd jackets (so they were cheap for my teenager budget). I had a matching jacket and vest in a navy chalk stripe as well as a navy DB odd jacket, both of which I would wear with grey and cream odd trousers in order to get my money’s worth. And you know what? I think these looks were pretty good, retroactively working as a “spin” on Morning Dress (a stretch but thats okay). I was hooked!
In fact, my first ever custom suit was a navy pinstripe DB, made by Indochino from linen because that particular cloth was on sale. Even though it seems like a typical dandy mistake that most menswear beginners regret, I actually wore mine a lot. Early on, I didn’t treat it like a summer suit but simply a pinstripe suit, which means I wore it with not just ties and polo shirts but rollnecks as well (lol). This shows a lot of the #menswear influence of which I was certainly not immune.
I soon locked into my POV and most of my outfits moving forward were done in service of the Golden Era or 80s Yuppie, as I wore it quite frequently with striped shirts and foulard ties; the type of tie was what differentiated the two. I even liked invoking true Golden Era style by wearing the suit with a dark shirt and light tie, though I was very aware that I looked like I was in Guys & Dolls or the Party City Gangster. I kept that thing from 2015 all the way into when I had my stint at Ascot Chang.
As time went on, I also ended up getting a few true vintage ones in brown, grey, and navy. The latter in particular was the most interesting as it not only was made of a heavy flannel (which means I didn’t wear it much) but was a mid 30s European model as it had an interesting shape, 4×2 closure, and a mix of belt loops, fishtail back, and side adjusters. As I got more comfortable with my style, I wore them not only to vintage events but to work as well!
I even got a chalkstripe sack suit on eBay, which only furthered how important the Pin/Chalk-Stripe suit was for my style. This was the one that let me lean more into ivy and contemporary menswear with my club and regimental ties allowing me to send up Jake Grantham with ease. Unfortunately, I later found the legs too tapered for my taste (I actually got them tapered when I got them, shame on me) and ultimately sold them to a friend. On a related note, I also passed on my 40s DBs as I wanted something less structured and with a higher buttoning point.
This resulted in a Pin/Chalk-Stripe suit sabbatical. It wasn’t that I no longer liked them but that other things took precedence, such as building up the other things that were iconic parts of my wardrobe: solid DBs, cotton suits, checked jackets, Alden loafers, and big pants. But as you know, this upgrading era eventually slowed. And when the opportunity came to buy new things, it ended up being less about experimenting and instead was more about buying what I’ve always enjoyed. And so came my Atelier Fugue navy chalkstripe DB.
It’s only been a few months since I received my chalkstripe DB (it came in February) but as some of you have seen, I’ve been wearing it quite often. That’s not to say that I was without apprehension. I wasn’t sure that such a “bold” suit fit what I was doing or that my money would have been better spent elsewhere. But I was wrong. This was the right move! It’s like I’ve reconnected with a childhood friend, where hanging out is just as natural as it was when we were kids. It’s all the same things: chambray/denim shirts, knit wear, and a healthy swath of striped shirts and geometric ties. Of course, friendships also develop, and so has my use of the Striped Suit. The garment is ripe for playing, whether its by leaning into the sexiness with an open shirt or adding in casual elements like denim shirt or an aloha. Whatever the case, styling it is just so easy and makes sense for my life!
It certainly feels like a full circle moment where I’m really just doubling down on who I was when I was 18. The outfits with the suit that I’ve worn today are largely similar to what I’ve worn before, with a few being nearly-verbatim send ups of old outfits. I can cosplay as myself as well as make a return to doing all the Apparel Arts and 80s yuppie outfits I’ve always enjoyed. It’s proof that taste has always been there, just with a few executional tweaks. Wearing the Chalkstripe Suit is a way to honor the Ethan that came before. But it also seems to look to the future as well.
In my post about the grey suit, I shared how as I got older, I started to appreciate not just sobriety (in terms of styling) but dressing for the professional I was. After all, it’s easy to see grey as corporate, especially compared to brown (casual) and navy (versatile/agnostic). I’m getting right up against 30. This is my second job as an Account Manager, which plants me firmly in my career. A grey suit fits that “guy”, but a Pin/Chalk-stripe suit doubles down on this stage of life. Instead of it being a fun cosplay (nothing wrong with that), it simply makes sense for who I am and who I’m becoming. (Though I’m sure conservative dressers will still say that I haven’t earned my stripes yet).
The formal aspect lends the Striped Suit for being my natural go-to for Occasions, though like I’ve said before, I don’t often have anything truly special that requires a specific look. It’s always up to me to determine the formality…at least for myself! It’s not that any of my other suit and tie looks wouldn’t work for a work dinner or evening cocktails, but that the Striped Suit simply makes it more special simply due to its inherent vibes.
After all, the appeal of the Stripe Suit is indeed about wanting the power it has, whether you’re ready for it or not. It’s a challenge to be clear, but a fun one that I find quite rewarding both in my expressive activities and my own confidence.
The Pinstripe and Chalk Stripe suit simply exudes gravitas, balancing bold appearance with a sobering attitude, making it stand tall against its solid and checked cousins. It’s not a menswear requirement by any means, but if you feel the allure of the lines, you should definitely embrace it, full force. Its grandeur lies in the fact that it is always saying something thanks to the vertical lines that are ever present on the garment.
For me, the stripes call to mind the pages of a diary, serving as an invitation for me to document our histories and dreams in cloth as we wear them. The lines then become strings, tying me to who we were, who we are, and who we will be.
-End of blog post-
The Pinstripe & Chalkstripe suit is also the subject of the latest episode of Style & Direction! While we do get into the weeds on what exactly counts as Pin vs. Chalk (we should have figured that out earlier), the main focus is about our love affair with this iconic pattern and how we like to leverage it in our style. Unlike me, Spencer has only owned one Striped Suit and he unfortunately passed it on a few years ago; he’s definitely in the market for one if the price and fit align. MJ on the other hand has never owned a Striped Suit but he’s obviously sold on the idea.
It’s been a while since we’ve discussed a specific garment or clothing itself in general, as most of the recent pods have been about philosophy and the approach to dressing. This one is a good return to form and makes for a fun episode!
Podcast Outline
1:25 – Topic Intro/What is Pinstripe?
13:00 – It has Meaning
27:36 – Fabric Types
36:22 – More Connotations and Styling
54:05 – Ethan and Spencer’s Pinstripe Suits
1:13:18 – Wrap-up
Subversive/Casual
Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. Oh and don’t forget, we do a podcast every two weeks!