My toxic trait, other than wearing a tie at all times and being obsessed with “POV” to the point of cosplay, is that I love talking about dating. There is something so deliciously juicy about it, from the banter in the first few days of conversation to the heavy discussion of figuring out if something is getting serious. It’s clear that I’m just a huge gossip who loves hearing the tea.. I’m sure that my puritanical and sexless background through attending Christian Education my whole life (which had a very “don’t worry about it, God will provide but also feel guilty about all sex-related things”) has something to do with my inherent fascination with the topic.
There’s also the fact that dating is the true arena of articulating expression and evaluating the effectiveness of execution. That’s just a pretentious way of saying what everyone already knows: clothes matter because people may make judgements about us. And while we may make concessions for stuff like what we wear to work, it’s a bit tougher to do the same with our dating attire. The outfits we wear when we are dating are an attempt to express something that will intrigue or impress someone while at the end of the day, still being able to communicate authenticity.
This focus on achieving social benefit turns what a fun exercise in self-expression into something pragmatic and potentially anxiety inducing! That being said, it’s also a positive opportunity for us to know ourselves and what we want to achieve with our clothes. To put our social-money where our menswear-mouth is. And that’s what makes dating (and clothes) such a fun topic! 
Before I go on, I do want to say that this is more of a retrospective of my experience rather than a current analysis of the current dating environment. Overall, I do think it’s gotten better to date when you have a bold style! But that wasn’t always the case, especially for me…
As most enjoyers of classic menswear will know, our chosen mode of dress isn’t exactly the most ideal thing to wear when dating. That’s because CM/tailoring suffers from its long history of elitism and class, which makes such attire marred by potentially unsavory preconceptions to many people. There is also the fact that tailoring with ties is no longer obligatory or socially necessary for most social occasions. I think that this has been a good thing for egalitarianism and for the spread of various avenues of expression! But it also lead to enthusiast’s decision to wear it to be awkwardly perceived as overly formal or being a bit of a try-hard, which is probably not want to you want to come across as when going on dates.
Classic and vintage menswear (suits and ties specifically) isn’t bad per se, but since dating is about appeal and external social benefits, there is always the argument that you should probably wear something else that doesn’t invoke overt connotation in order to have a better time, especially if you tend to date people who aren’t into fashion as a hobby. It’s a similar mindset to what to wear to work: be normal and don’t detract from your work. After all, the cardinal rules of dating are to be attractive and not be unattractive. This is harder to do when you’re into vintage/classic clothing as you will always be combating the existing context of menswear.
Of course, all of this is coming from an absurd cishet man who intentionally wears anachronistic clothing and a fedora on a semi-daily basis. It’s no surprise that my chosen mode of niche dress made making a good date fit “harder” than it needed to be!
To be clear, I do think that dating and relationships are more than just the clothes we wear, but since making outfits is inextricably tied to knowing yourself and expressing it, it can be hard not to have a bit of an existential crisis when dating attire is concerned (I’m talking about myself tbh). The “game”, if you can even call it that, is about balancing what you think looks good on you with what should also be read as “good” by the other person. And while sentiment has improved considerably over the past for years, classic menswear and vintage (especially in trad styling) is still rough to be read as “good” when in non-special occasion situations.
I don’t share this just to be negative, but to encourage a healthy amount of self-awareness when getting dressed. So many people, especially young men, have been taught by blogs and Youtube hustlers that putting on a suit and tie is a magic key to getting dates when in reality, its much more nuanced than that. It’s not impossible, as you will go on to read, but it’s definitely a struggle whether you’re in the dating scene or in an existing relationship (as some menswear friends have told me).
It didn’t help that at the peak of my dating 3-4 years ago, I was ever so reminded that my style wasn’t the best for dating. According to a 2021 thread in one of my Asian American groups, the most a guy needs to do is wear a slim-fit button-up with the sleeves rolled up. In all honesty, this is probably good general advice today (especially if you’re in the millennial demo), even if it’s a bit of an agnostic look.
People love that shit. My hot take is that the nearly-universal attraction to the slim fit shirt + sleeves rolled up is actually what keeps us from progressing further in menswear. Thankfully, Gen Z has largely embraced wide fits as well as more expressiveness in overall attire, so perhaps things are looking up for the use of class/vintage menswear in dating (and the overall world). But this “game of appeal” must still be played, even if we are able to wear more of what we like in the current day.
As Yung Chomsky stated in what was ultimately the proto-version of this blog/pod, “[On a date] you are showing your social aptitude: the ability to dress one step better than your surroundings, but ONLY one step. That takes skill.” To be clear, this “step” is referring to edge (like sex appeal) and not necessarily formality, even though sometimes it can incorporate such elements. There are certainly items and style moves that make vintage/classic menswear attractive and even sexy! But there are also many things that are not, which makes this a rough game to play. Add in the fact that tailoring is not required for dates of any kind (which is an overall social good, mind you), it just makes the decision to wear it a potentially difficult one, especially if you opt for bolder stylings and are on the younger side.
In a Jackal Mag article that has unfortunately been deleted (all I have are the Reddit comments reacting to it), Aleks Cvetkovic wrote an article detailing how menswear guys love wearing “woman-repelling menswear”. Aleks ends the piece by saying that “[if] you’re single and dating[…]it’s beige chinos and t-shirts all the way.”
The article is a nice testament to how some guys dress for themselves instead of basing it on what is attractive to women (or our chosen gender). But the piece also makes it clear that even storied-menswear folk are aware that their favorite garments have dating and social shortcomings. Even the dudes in relationships say in the piece that they have to save their wild tailoring and accouterments for when they’re not on dates. The struggle doesn’t seem to end even when you’ve found your partner!
All clothes will say something about you but classic menswear tends to say a lot–whether it’s what you intend or not. It’s not even inherently about class, but about the vague ideas about lifestyle and personality we always attach to clothes. And with the rise of social media and online dating, you may not be afforded much chance to let your match know how in spite of your tailored clothing, you’re actually a slouchy and easy-going guy.
It can also be a “curse” to remember that most people’s idea of an attractive outfit (at least for Millennials) is still a slim fit shirt with the sleeves rolled up. Gen Z’s style, as well as the current fashion zeitgeist (like Tumblr) has more shades of classic menswear such as a bigger pant, camp collar shirt, and a Doc Marten loafer…but that’s still not an OCBDs and a sack blazer, let alone a funky foulard ties and fedoras.
In fact, I was so anxious about reconciling my taste with dating (and social) attire. Looking back, my reluctance to dress the way I wanted in a world where you should express yourself lead to a lot of bricked fits and wasted time in my menswear journey.
You see, I used to approach my love of menswear a secret shame. A decidedly open secret, as most people would eventually find my plethora of fit pics on Instagram or tumblr), but one I tried to keep down as much as I could. Much of this was because I didn’t want to be put into a box. Yes, I liked fedoras and wide leg pants, but that doesn’t mean I enjoy swing dancing or watching Golden Era movies all the time; I just like the proportions and intentional styling. And even if I (and my style) was starting to have a bit of attention on social media, that didn’t mean everyone else would be into it too, let alone understand it. What I did know was that I did want to date…and still be myself (kinda).
As a result, most of my early dating attire was rather plain and palatable. I would wear crew neck shirts/sweaters (maybe a sport shirt) with slim jeans and boots (sometimes loafers); the vintage personality would come with my leather jackets. This attire, which was definitely inspired by MFA, was intentional, “currenent”, and contained a few nods to classic and vintage menswear. When I did introduce a suit and tie (which was rare), the styling and fit were always modern and largely within the zeitgeist of the time (vibrant blue with tan shoes) instead of the big fits and bolder, period nods that I actually wanted to wear.
Keeping my sartorial self hidden (but clearly bubbling under the surface) did work to an extent, as I was able to go out with some lovely people and largely escape the “dapper” connotations; I wasn’t immediately swiped left on for being a 18-20 year-old in a vintage suit. I told myself that this was purely pragmatic, a way for me to ease my partners into the person I wanted to be. However, I soon realized my folly.
Since I had made it appear like I was perfectly able to not wear suits daily, it made the days I did wear my suits come across like nonsensical cosplay. My pursuit of expression, writing a blog, and overall enjoyment of flea markets, trunk shows, and other menswear events was considered jarring. I realized that my friends, who were all used to my regular attire regardless of whether they were fashion people or not, actually saw the real Ethan. That’s quite a red flag! And while clothing isn’t a replacement for a personality, it was clear that I wasn’t embracing what was clearly important to me, which definitely lead to and highlighted my other personal issues and generated more inconsistencies. There was a lot to work on!
If all of this sounds like the ire I experienced during the awkward stages of my overall menswear journey, that’s because it basically is! I only realize now that so much of why I clung to slim fit suits and other things not in my Q-zone was because I wasn’t confident in who I was, at least to the point of knowing that others would accept me, let alone go out with me.
Thanks to Rules 1 and 2, I was convinced that menswear, at least my chosen mode of it, threw a wrench in the dating best practices. I felt that my chosen taste in attire was always going to be jarring and that because I had willing picked something “bold”, anachronistic, and clearly inconsistent with most people’s taste, I would be my burden to forever keep at bay (similar to me being obsessed with listening to/writing film score). What’s funny is that I also didn’t feel good about what I did wear on dates; I assumed they were marginally better because they were more modern. I was clearly setting myself up for failure, not just in how I presented myself but in how I felt about myself.
It wasn’t until I started expanding my circle of friends that I realized that I could still be me and go out on dates. While they weren’t all daily suit and tie wearers, they each had distinct styles that they would seldom edit (at least in broad strokes) when going out on dates. “If she’s going to see me in a sportcoat on Date No. 3 (as well as on my ig), I might as well wear it on Date No. 1”, my friend told me during a hang out where we were killing time before he left on said date. If he could do it, why couldn’t I?
There were also my female and queer friends, who were always unabashedly dressed as themselves on dates (while still balancing appeal). In fact, some of them even told me that they intentionally invoked tropes of vintage styling in order to attract the people they wanted. I admired that they embraced expression and authenticity from the get-go. And even though it’s definitely a different experience for queer relationships, there was still overall sentiment that I found kinship with: Dating will always have its challenges, so we might as well look the way we want to look and wear what makes us happy!
As was the case with my menswear journey, I first eased into Drake’s and various ivy-esque stylings for most dates, wearing jeans with Esquire Man shirt-tie combos as a way to reference my 1930’s styling and my participation in “current” (but niche) menswear while being palatable to an early to mid-twenties audience. It helped that I also felt a kinship with that style outside of dating and considered it a natural extension of my style rather than a cop-out.
It’s also important to note that I’ve always had more traction online dating than generating IRL interest, which meant that I would know which days would benefit from a pragmatic investment. In other words, I would wear my beloved bow ties and white suits on the days I did not have a date.
To be clear I still wore ties, sportcoats, and even full suits when going on dates. After all, it was what I felt good about and the most natural for me. Plus, it just made sense to preempt my potential future relationships about my sartorial habit and understand that it’s just the clothes I happen to enjoy wearing, rather than any social climbing or elitist bit. Instead of keeping it hidden behind “normal guy attire”, it was out there!
Dating will always nerve wrecking for sure and I was well aware that my attire may not do much in attracting more people, but at the very least I felt good about what I wore when I did go out. I started to see that my issues in the past were not about society not liking the suit, but simply my own insecurities in how I dressed. Of course, this probably goes well in hand with the maturing of my style, to know that being casual or not in a tie wasn’t antithetical to my taste; I could still be me in other mods of dress if I simply did careful styling and attention to proportions. It also helped that I started to learn to be more cohesive with my expression with everyday elements glasses and hair, all to ensure I was expressing myself at all times without concession.
My prerogative was to express my personality and my interests. Outfits are not a replacement for a personality, but they do say something. While you may think other wise, I felt like I was excuding a bit of artistic flair, comfort, and fun with my attire in a way that I didn’t do before. While anyone can wear anything and watch movies, write music, and do film photography, I thought my clothes helped further that and add more to the conversation.
At the very least felt like I was being myself, putting it out there, and full-sending it. It helped me be more at ease, which naturally lead to a better profile that was authentic to me (rather than try to over edit myself). To be clear, the overall amount of dates did lessen due to me putting more of myself out there, while wearing clothes that say a lot to being with, but the quality of who I talked to was better, with a more positive reception to my style. This helped me feel even more emboldened to wear outfits that actually matched/expressed my taste. It was proof that if you embrace what you like, other people might like it too, and that it’s possible (but still hard) to be fine socially (which obviously applies to more than just dating)! While I can’t escape some
All of the anxiety from dating (as well as other things) has helped me become more in-tune with my wardrobe and overall style.
All that being said, I sill do a bit of curation when dressing for dates. The curse of Abed-brain is that I will always be aware of the connotations my clothes and outfits will have. While I always feel great in any outfit I wear (and I know I’m at least a little handsome), I know that certain garments, despite my best interest, may be read as frumpy, a little odd, or might have too much to say. I’m talking about stuff like bowties, fedoras, and gurkha shorts. That’s not a bad thing, because sometimes I like dressing like that on purpose. But as I said before, I’ll just save those solo days.
On the flip side, I am aware of what outfits are rakish, cool, and sexy, both to me and other people: tonal pairings, black loafers, leather jackets, rayon shirts. They certainly look good on solo days but I also know that they would be great for dates, especially if it was something in the evening. The best part is that wearing those fits never feel like I’m hiding anything or cosplaying, even if it is meant to also appeal to someone other than myself. It’s all rooted in the clothes I already have and the outfits I inherently make on my own!
That’s why I don’t have specific uniform for dates (as some people do), but rather a guiding philosophy to simply think about what vibes I want to put out there, as well as think about the vibes from the date and person. It’s not just about knowing what not to wear (in order to avoid negative connotations), but to also know what works for the intentional and authentic message I want to put out there with my clothes. And honestly most of it isn’t dissimilar to how I [arbitrarily] pair outfits with the Occasions of my everyday life.
Ivy or Esquire-Man makes sense for a coffee date or a casual bite. If it’s even more casual, doing rugged ivy or something western or SFC-adjacent makes more sense; I often do this when I want to play up the “cute” vibes rather than intellectual or artist-inclined (I shuddered at that sentence). If cocktails are suggested, a minimal take on tailoring (like Armani) works to class up the vibe. And if you want some sex appeal, going 70s (or 40s does 70s) with a severely unbuttoned rayon shirt does the trick; I simply decide if I’m doing a suit or doing separates with a flared pant.
To sum up, if its a daytime thing, I try to push for something fun and jaunty. If it’s in the evening, then a darker palette and some edge is the way to go. Obviously the goal is to show the full breadth as the dates hopefully continue. But no matter what, every fit I wear are tied together by silhouette and references to vintage/Americana, so that no matter which one comes first, it all will make sense. No fit will be too jarring from the other! Oh and I make it a personal rule to wear the fit all day; I don’t change just for the date!
In retrospect, it’s funny to think about how much Dating Attire used to stress me out, especially now that I have some gravitas (age) and the teeniest bit of social clout because I’ve been doing this for a long time. It just means that my tie-wearing ass makes more “sense” to people now than ever before! I also can’t escape the fact that the zeitgeist has embraced elements of classic menswear and even made fashion an acceptable hobby for everyone. Overall, I think it’s easier now than ever for menswear guys, specifically ones with bolder style, to date while wearing their favorite clothes.
But even though fashion-as-a-hobby is more popular in the mainstream now, I will say that it still matters to be a bit selective in your dating. Nothing compares to going out with someone who either shares that passion or at least values a bold approach to self-expression. It just leads to more cohesion, coherence, and dare I say it, self-actualization.
That’s why I’m extremely lucky I get to be with Isabel!
Isabel is a major reason why I’ve been able to achieve self-actualization with my style and feel empowered to wear what makes me happy. That’s because Isabel’s own beliefs in dressing for expression and being firmly okay with Standing Out, even if what she likes to wear will be read as silly or even weird.
As you guys have no doubt already seen, Isabel’s style is very cool. You may consider it artsy or even a bit of Bookcore and that’s because it’s authentically tied to her personality and interests. Since she is a freelance editor (and previously worked at a performing arts theater), she is all about supporting independent makers and brands, which means she ends up with very unique pieces. Isabel also likes painting and poetry, which lend themselves to bold colors and graphic tees. She also likes to prioritize comfort, which means she wears wide leg, high-waisted pants, flow-y dresses, and a penchant for layers when she’s cold. And when all that’s said and done, she also likes to wear things for no reason, which is why you may see her wear funky printed socks or leggings with cute animals on them.
Isabel isn’t a “true” fashion mfer but she clearly takes an interest in expressing herself, especially through her clothes. And this was something I noticed right away, both in her dating profile as well as in our first few messages and dates. Picking up on that allowed me to feel comfortable dressing as myself from the get-go. She had no issue with the fact that I wore foulard ties and plaid jackets to get boba in the park or that I was wearing a runaway collar and cowboy boots to the bar. She never read it as me trying to be too formal or being too bold, presumably because she already saw herself as bold. It seems that it was probably a good thing that I dress the way I do, even if we don’t have the same style (or do we).
This continues to today, where we largely wear whatever we want on dates. I follow my little vibe guidelines and so does she! Sometimes she takes the opportunity to match them or wear something fun. Other times, she dresses purely comfort, as we both work from home and don’t need to leave the house (though even her comfort looks are a vibe). We always dress as ourselves and we know to expect that from each other. Neither of us are ever caught off guard and no one feels insecure or feels the need to edit their style…at least when it’s just us. That being said, we both like the the challenge that External Occasions presents us and so far, we’ve been just fine!
And when asked “if Ethan Style is actually attractive”, she said that she felt it was definitely appealing. Due to her push for expression, she admired the fact that I had a style and enjoyed the challenge of putting things together. It never read to her as overly corporate or try-hard, which can be attributed to my inherent slouch and maximal approach to menswear, but also the fact that we are clearly on a similar wavelength. I think the way I dress shows an affinity for art and creativity as well as fandom, two things that we both are into. So while it wasn’t necessarily the specific clothes I wore, it was clear that dressing as myself allowed me to put out the best vibes, which was attractive to her. It is possible to balance authenticity and appeal— it just takes finding the right person!
This makes her enjoyment of my fits a definite bonus, even if she doesn’t always know exactly what “Esquire-Man” is or what comprises true ivy canon. It might be selfish but important note), but I’m just glad I no longer need to have two separate wardrobes: one for my gf and one for me. I don’t have to look forward to the days I’m not around her in order to wear what I want! That being said, the one outfit/style she isn’t the biggest fan of is the school boy look. And you know what? That’s a fair assessment. It’s silly, but I love it!
I’m just happy we got together when my style had already matured. I’m not sure she would’ve enjoyed the existential crises of authenticity that I had when I was younger (and for that I apologize to my exes, who didn’t deserve to be put through that lol).
In the end, it’s all just clothes, which do not make or break a relationship. But dating attire will always be about expression and articulation, whether you’re making fits for first dates or figuring out how to keep your menswear hobby while still making your partner comfortable on date night. I know that everyone gets into menswear and their relationships at different times in their life, so there isn’t a right moment. But that shouldn’t be a negative.
Like I’ve said many times on this blog, I truly believe in the expressive merit of classic and vintage menswear. So while it may not be the sexiest thing to wear, it can still be something cool to invoke in dating attire. It should always be fun! The best advice I can give (and I’m not qualified for that in the slightest) is to always be aware of your vibes as well as the type of person you’re going out with. I will always prefer to dress like myself instead of over-editing myself just to get a date. And if you ask me (or Isabel), I think I dress cute!
As I said before, things are much better now than they were when I was a teen in college looking for a date. As fashion has become an egalitarian hobby, we’ve seen more opportunities to get bold and expressive when going out on dates. And that means we can wear menswear on our dates, provided we’re going out with people who at least won’t be put off by it. I can honestly say that if I was single, I’d be just fine wearing what you guys see me wear on a date today!
To that end, I talked to Spencer and MJ for their thoughts on Dating Attire. It’s a really fun episode, especially considering the fact that both of them are currently in the Dating Trenches. In other words, they have more to lose (or gain) from wearing a bold outfit on a date. I’m not immune however– I also get more in-depth with what I wear with Isabel and explain in her own words, why it all worked out.
Yes, I actually discussed all of this with her in preparation for this article! She just didn’t want to be on the pod…yet. For now you’ll have to enjoy the pod, this blog, and all the photos showing that perhaps Dating Attire isn’t a complicated topic so far. It’s best to dress like yourself and find the right person.
Podcast Outline
- 14:31 – Topic Intro
- 17:18 – Effect of Dressing Up
- 28:26 – Dressing for Who You Want to Attract
- 42:55 – The Importance of Dressing “Nice”
- 53:17 – Moving Into Dressing How We Want
- 57:47 – Relationship Attire
- 59:16 – Spencer’s Speed Dating Experience
- 1:10:51 – Ethan’s Dates with Isabel
- 1:30:52 – Wrap-up
Recommended Reading
- My Valentine’s Day Series, written in college during the first few weeks of my blog.
- A blog post where I tell guys not to wear a tie on Valentine’s Day, for fear of offending.
- We’ve also talked about Dating Attire and perceptions of Menswear back when we used to stream!
Thanks for listening and reading along! Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord.
The Podcast is produced by MJ.
Always a pleasure,Ethan M. Wong (follow me on IG)