On Dressing Authentically

Despite the variety of styles, I think we all dress authentically. Whatever that word means!

A common theme of my essays (and the podcast) is this idea of authenticity. In the beginning, a lot of the blogs were done around a specific authentic basis: period or Golden Era tailoring. As time went on, the message about authenticity became about different aesthetics like ivy or International Classic (via The Armoury), still revolving around specific cues or items. However now, authenticity to me (if I’m even using it correctly) is simply about…well, me. I stress that the clothing you wear should feel easy, natural and ultimately, it should make sense for your life. In short, authenticity really means nothing, since the deciding factor is literally made by you.

Take a listen to the discussion I had with Spencer on the podcast below. It will help frame the writing that follows!

This can seem wild but it involves everything I’ve been into throughout the course of my menswear journey: berets, milsurp, gabardine shirts, high waist/wide legs, white socks, and wallabees. Pretty authentic!

I say this in the podcast, but the this idea of “dressing for yourself” is a rather new idea. That point came up when I was having one of my many discussions about menswear in my Patreon Discord (which is accessible to subscribers). It could have been about figuring out how to wear a beret or trying a wide leg opening, but most likely, it was related to the POV essay where we talk about using clothing to look like “the person you want to be”. I call that personal authenticity.

To be clear, the term “personal authenticity” is a loose one, but like slouch (and a lot of other things I talk about on this blog), that’s entirely the point. To me, authenticity simply means being aware of your choices and being able to act on it. For the sake of clothing, this just means dressing how you want and presenting your aesthetically in the way you see fit. My definition of authenticity is intrinsically linked to slouch, POV, and practicality with part each playing into and informing the other in a (hopefully) natural way. There is some effort and self reflection involved, but over time, you’ll begin to know what is authentic to you, whether its trying a completely new style or simply enhancing your existing one. I also think that it’s perfectly fine to adjust your authenticity based on different contexts, so it helps to keep the use of the term quite varied and open.

I also think that many people today (as evident in the comment section of my feature on Permanent Style) have the odd thought of connecting authenticity to being as completely original as possible. Ergo, if you acknowledge someone else doing something, you can’t claim that as authentic. That’s completely bonkers to me, since interest and inspiration is key in trying anything for yourself! To be clear, my definition of authenticity hinges on how much you like something and how confident you are in applying it to yourself; being aware of your inspirations is just helpful in realizing why you like something and how you got the push to try it for yourself. Fashion (and music, like most art forms) will not pass that authenticity test, at least if you have have that rule for it. What matters is that I know what I like and what intrigues me!

As I reflect on those conversations, it seems that for a long time, dressing was based on external forces and not really a personal hobby. I personally see this as a lack of personal authenticity, at least when compared to how I act on it today. Tailoring and classic menswear was considered the de facto uniform of the world until the midcentury, where casual style (like jeans and designer focused clothing) diluted the uniform. Even then, dressing for individuality or for your authentic self was rare (yes I do know that a few Golden Era movie stars used their own clothing, I’m mainly talking about regular people).

You had to dress a certain way to fit in, whether it was socially or professionally. If you really wanted to wear a certain thing, you better damn be sure that your career or context could fit it. For example, I knew early on that I liked suits. My parents told me that the only way it could happen was if I got involved in corporate America; they preferred law or finance. The idea that a creative or someone not involved in big corporation could be into wearing suits is typically considered odd. I never liked that. It felt like other people were dictating my personal authenticity.

That’s why I’m very happy that fashion has become a personal endeavor, almost completely free from outside contexts. Guys at huge tech companies can wear Dickies workpants. Painters can be tailoring enthusiasts. I generally praise the death of dress code and am largely supportive of the fact that we are seeing a new wave of people incorporating classic menswear into their style, even if it is tangential and different in specific execution. We can dress however we want, career or context be damned- That’s true personal authenticity for you. Clothing become a creative endeavor, one that while malleable by mood or context, can still be used to exude what you intend.

This [relatively] sudden jump into clothing as a sense of personal authenticity is not without problems, as I sometimes butt heads with many people over this concept. Keep in mind that, I am a part of a younger generation where we’ve been allowed quite a bit of freedom in crafting our identity, both in person and online. This, along with the fact that I live in LA, means that dressing authentically to me is quite easy and without many barriers to entry (I’m sure NYC could be similar). And lets not forget that my mode of dress is classic menswear, an all encompassing term that I use for milsurp, workwear, vintage, and tailoring. Compared to all the other styles out there, my clothing is seldom problematic to execute on the daily. I can dress and be the person I want to be without much pushback!

To be quite frank, most people who have issues with personal authenticity tend to be from an older generation or at the very least, operate on a similar mentality where they find it odd to dress completely for themselves. Perhaps that’s why I’ve gotten pushback on the ideas of POV and slouch, though it can be hard to fathom some of my ideas in a conservative place (even if I don’t truly believe your boss is going to call you out for a cotton suit or a rolling OCBD). But hey, that’s why I said my definition has room for concessions! I’ll expand on that later.

Anyway, this problems with the new idea of freely expressing personal authenticity typically takes two fronts. The first is getting authentically into classic menswear in general. This is mainly an issue with newbies to clothing, like on MaleFashionAdvice. Everything outside of a tee shirt and jeans is seen as “too much” and they can’t get beyond the Basic Bastard (which is still perfectly fine to wear by the way). People are scared of not looking like themselves, which to me is honestly quite odd because it requires you to think about what looking like “yourself” even means. And people change, don’t they? Why can’t that guy with the cool clothes be you?

It seems like to me that their issues with authenticity focus on effort. Those that are familiar with the blog and podcast are the main ones who point this out, as being “natural” in clothing is such a big part of my message. I certainly empathize- dressing up can be tough to get into especially if you haven’t done it before. Classic menswear also happens to be a mode of dress that is connected strongly with perceived class or status. The democratization of menswear has helped its wearers become more diverse, but a regular passerby (or friend or coworker) may have some reservations about your attire.

This is why I try to share as many old photos of myself as possible. Menswear, like any other creative endeavor, will always have some effort attached to it, perhaps more so at the beginning. It may not be good, but that’s okay! Mistakes will be made. Honestly, the first step is to get the idea that menswear is the most “stylish” or “correct” way to dress out of your head. It’s also not something you can cheat code your way into. Ultimately, if you aren’t already attracted to the aesthetic, then don’t force it. That’s not authentic!

However, if you do find some inkling into classic menswear, then that counts as budding authenticity to me. Hell, maybe this means that authenticity is something that can grow and develop! After all, knowing that you like abstract jazz (POV) but you gotta start out by playing Suzuki minuets. You can obviously look up jazz standards and other exercises to get into that mindset, but it’s okay to take that first step. You’ll practice, try new things, and make mistakes, but if you really are passionate about it, you’ll absolutely improve. Again, jazz isn’t the epitome of piano music, nor is purely classical sonatas, so it helps if you just look at it as a medium to accomplish the “sound” you want. Translate that to menswear and using it as an avenue to the “look” you desire!

And honestly, people aren’t going to know the context behind your authenticity. People might assume you’re trying to be fancy or that you’re attempting to be an influencer (if sharing fit pics on social is your thing), but only you will know what you’re trying to do. Like with practicality, it helps if you reference your personal life into your menswear, emphasizing the personal nature of authenticity. Workshirts are great if you want the idea of a button-up but without the dressy poplin vibe. Incorporate sneakers or merch (which is definitely the subject of a future pod) as you see fit; a lot of classic menswear is certainly possible with those items.

I definitely believe that classic menswear is broad enough for people to find their way in and get to the fits they want to wear while still being authentic to themselves. And once you get to the slouch, it’s heaven, trust me. You don’t need to be relegated to simply playing with “happy socks”- there are so many details and nuance to play into, all of which are becoming much more prominent and acceptable in the post-pandemic world.

This brings me to the second issue: trying new pieces/style moves once you’re already in menswear. This problem is probably discussed most of all in existing communities rather than newbie ones. The problem here is that these guys tend to already feel like they’re being authentic, so when they’re confronted with the possibility of trying something new, they feel resistant to it. It feels inauthentic to try it out, but this time instead of being sold on an completely new style, it’s about specific pieces like the beret, short jacket, or a cotton as a suiting fabric. Perhaps incremental change is the hardest to do!

I know this was a big problem for me early on. As you recall, knit caps were my first piece of headwear that wasn’t a fedora (and even back then, I didn’t wear fedoras nearly as often as I do now). It was tough, because at that point I was concerned with the traditional ideas of classic menswear. Sure, I was already contemporary rather than period-accurate, but it was still much more formal in execution. But yet, there was simply something intriguing about the knit cap. It was useful but also decidedly more casual, echoing the cool vibes of my skater friends and the indie girls I had crushes on. I authentically liked it and incorporated it, even if it wasn’t congruous with my tailoring.

And guess what? It eventually became authentically congruous with my style, which ultimately lead to my adoption of the bucket hat and beret. With that throughline established, it lead to a gateway to other things which are now tenets of my take on classic menswear. Now that I think about it, that first use of the knit cap probably lead to a much more casual approach to menswear in general. All still authentic to me! It’s not an exact step-by-step process (especially since I process clothes weirdly and there isn’t an endgame per se), but there seems to be a theme when we look at how Old Ethan became Current Ethan.

Again, the issue about authenticity is solved by having an open mind, both about authenticity and menswear. On the former, its important to understand that authenticity can be built; it’s also impossible to truly know what’s authentic to you if you haven’t tried it. Nothing is completely natural to you at the get go, so it will involve some effort on your end. you shouldn’t shy away from this, especially if you consider clothing an artistic endeavor. All art has some effort to do, and the more you do it, the more natural it becomes; the effort becomes all the micro decisions you’ve already played out.

The former is solved by having an expanded view on art (here being in the form classic menswear) itself. Like I said earlier, I don’t consider classic menswear to be a monolith of tailoring. In reality, so many things fit into it, presumably because a lot of men’s clothing is based on classic designs. Chore coats can resemble sportcoats. Workshirts have spearpoint collars. Military chinos and dress trousers have pleats. Doc Martens look like work boots.

Let’s not forget that there has been plenty of historical precedent for many style moves as well. We might think of sweatshirts and sneakers to being streetwear only garments- photos of 1960s university students will prove otherwise. The plethora of documentation proves to me that classic menswear truly is a wellspring of ideas, all of which I consider to be strongly linked with a cohesive throughline. As a result, I’ve been able to add many things to my personal style in a way that is still authentic to my love of classic menswear. It didn’t feel like I was betraying my older tastes so much as simply adding more aesthetics/references to pick from, akin to how adding more tools to your tool box doesn’t mean you’re betraying the first hammer you ever purchased. And if you look out into the world of menswear, you can see plenty other people who approach style in the same way.

As I said in the introduction, clothing is no longer linked to specific careers or hobbies. It’s almost completely an aesthetic pursuit. This is why everyone I’ve met has had a widely different context and lifestyle, a fact that I celebrate and emphasize when introducing menswear to someone new. Spencer is a journalism student who wears milsurp and workwear. Chris is a barista. Henrik is a professor. Yung Chomsky is a podcast producer. Peter is an electrical engineer. Marco works in tech. Jamie is a photographer. Joshua is a guitarist. I work in gaming media. Broadly speaking, none of us have (or should?) be wearing classic menswear, but it’s what we like to do! Sure, some of us may play into the stereotype of a typical enthusiast in some regards, but personal authenticity is what truly makes each clothing choice interesting and ensures that we don’t dress like a monolith.

Maybe this just means that a “uniform” is simply dictated by the wearer, rather than external forces!

Obviously our contexts do dictate how we approach classic menswear, but again, the genre is so broad that we’re able to make it work and still be authentic to our tastes. There is that concept of Forced Versatility I talked about in the Practicality essay. Sometimes you like a piece of clothing so much that you adapt it into your style, even if it isn’t naturally congruous. Or you find a compromise to introduce your clothing habit into other parts of your life to make it more coherent.

Peter is a great example of that, rocking heavy workwear when he’s out in the field and donning custom tailoring and breezy 18East in his free time; both of these are an authentic part of his life and interests. Marco has definitely had a bit of that, figuring out how to combine motorcycle riding attire into his typically blousy look. And hey, plenty of film directors show up on set dressed particularly well (in their own way). I’ve done the same approach to my own contexts, referencing my plethora of subsets and inspirations, all exuding something dependent on what I’m doing. At this point, I hope that this variety and forced versatility is pulled off with ease. I’m sure it wasn’t always this way, but I knew that all the effort I did before would culminate into a much more natural (and better executed) result.

Even if we try to take all of this into account, the fact remains that only you will know what’s truly authentic. It really makes no sense to overly surmise if someone is experimenting in earnest or being a try hard with trends; typically their actions and what they say will clue you in on that. That’s why its always up to you to decide what’s authentic or not! And hey, with a new world on the horizon, dressing for authentic joy might just trump everything else.

I’m reminded of an unfortunate comment Marco got on Styleforum where someone laid into his style, implying that Marco was either trying to be someone he’s not and that he was going to regret it later. I can see how such comments would deter people into getting into menswear/trying new things with authenticity as the main focal point of the issue. However, that’s all bullshit because I know that Marco’s clothes fit him. he’s a dancer who lives in LA and rides a sweet motorcycle; I’ve also heard that his parties are quite wild. So to me, Marco is dressing exactly the way he wants to and he’s certainly giving off the intended vibe. That’s something I’ve tried to accomplish for myself.

I’ve talked about this before (like on stream), but I dressing like the person I envision in my head is one of my main guiding notions. It’s so much more than simply dressing ivy or workwear, but rather how Ethan would wear ivy or workwear. And being Ethan doesn’t just mean only being a suit guy. Rather, being Ethan involves carrying a film camera with you everywhere, discussing film score, and grabbing boba…all while dressed in classic menswear. Hopefully what I wear feels less like a costume and more like a uniform of suits, making sense for me primarily because I make it so.

It seems again, the issue that people who critique our niche tend to project is that clothing should signal something truthful your lifestyle and that its bad that other people will do the same. I never liked that because it not only makes clothes feel more important than they are and that it discounts your ability to control your authenticity. It’s also leaves no room for irony or subversion.

I also find the costume argument a little silly because that word really doesn’t mean much. It could mean a collection of clothes that cohesively point to a specific aesthetic, but maybe that’s because I relate costume to uniforms or starterpack memes. You could consider a few of my outfits a form of Bryceland’s or Drake’s cosplay! Let’s not forget how people are literally lifting Seinfeld and Sopranos vibes for their own outfits.

And when it comes down to “bold” things like fedoras or 3PC suits, I’ve started to shut up about how odd their are, especially if they’re done well. “Done well” is another loose term, but you know it when you see it; it’s pretty tough to call them out when Ethan Newton and Mark Cho both provide ample evidence of wearing each of these things. You could call them a try hard, but I don’t think it really matters since its authentic to them. It’s just about wearing what you like in a cool way.

Hell, even if you think about it, the difference between being a try hard and a truly stylish guy simply depends on what the dresser’s confidence and overall execution. We have an idea on the Patreon Discord where people often question whether an “incongruous” item feels “swapped in” or feels like a natural extension of style, especially in the eyes of a passerby. But honestly, the conundrum and what other people may think is not worth losing sleep over- that’s I recommend that you surround yourself with people who are on your wavelength. It really helps build that confidence, ease any bricked fits, and if you need it, provides context for your authenticity. Working in the industry definitely helps, but I still don’t think that your job needs to dictate your style (at least within reason).

Even if that’s too idealistic, I really do think that classic menswear still involves a lot of nuance for you to stay true to yourself and still be “acceptable”. You can even subvert the ideas of authenticity, which is what makes it so fun! Owning that idea of fun is a huge step in gaining mastery over personal style. The ability to confidently walk out dressed like yourself is something to celebrate.

While I don’t want you guys to have deep meditations and philosophical discussions on authenticity, I definitely think its a concept to keep in mind when dressing- especially since being authentic to yourself is a big component of POV and slouch! Personally, I like the challenge of figuring out what simultaneously intrigues you and stays true to what you already wear. It’s not something to stress about, but to celebrate, with mistakes and wins along the way.

That could just be the creative in me, but hey, dressing up should be creative! Authentically, of course. (Whatever that means.)

Podcast Outline

  • 00:17 – Cold Open
  • 11:28 Topic start
  • 14:06 – What Makes Clothing Authentic
  • 17:33 – Menswear Isn’t Authentic
  • 27:02 – “I could never wear that”
  • 28:42 – Marco’s Thread on StyleForum
  • 31:24 – You’ll Know How Authentic You Are
  • 33:27 – Writers and Artists Wearing Tailoring
  • 25:24 – Variance and cohesion in menswear
  • 39:27 – Big Generational Differences
  • 41:34 – If It’s Authentic, It’s Authentic
  • 42:01 – Menswear has Trends
  • 44:07 – How Important is Consistency to Authenticity?
  • 48:48 – Work Appropriate Clothes
  • 1:02:22 -Trying to Put Authenticity in a Box

As always we followed up the podcast episode with a streamed discussion with our Patreon Discord, where we dive a bit deeper into how others define authenticity and how it differs from simply having a POV. I think Henrik says it best where POV is a preference where authenticity tends to be connected to or personal history. Kiyoshi added that authenticity is done via introspection rather than aspiration. I think that both are correct, leading to the idea that at some point or another, you (or your gut) will know what’s authentic to you.

And again, sometimes you just like it and make it so.

Recommended Reading

Sometimes I want to dress like a dude who wears tailoring, even at home. That’s who I am! I make choices based on that POV.

A 1940’s suit with a modern shirt and 60’s tie. Pretty authentic to my interests!
A good outfit that is practical but still has ideas of what I like from menswear.
Fedoras are something I enjoy, so I still find ways to wear it even if the pieces are more contemporary.
Sometimes when you love something (like a cowboy hat), you just gotta wear it, even if it isn’t congruous with the other items. You make it so.
Leaning into an aesthetic because you like it is perfectly fine.
You always find a way to mix things you love, like trad and milsurp.
I’m sure that having an affinity for dress fedoras can lead to trying other variations, like the silverbelly western style.
Summer means adapting what you like to the weather.
Another great mix and example of “forced versatility” where you adapt a denim chore coat as a top layer over a suit.
Ain’t nothing wrong with jeans and sneakers if that’s what you’re into! However the choices of which jeans and sneakers you pick are indicative of authenticity.
You can be a suit guy who likes unconventional shirting.
Sartorial guys do dress for the weather, just in a way that’s authentic to them.
We both like suits and high rise trousers, just done up in different ways.
Marco is one of the most authentic dressers I know, wearing items that appeal to him emotionally. Even if you factor in his LA lifestyle of dancing, partying, and riding bikes, I think you’ll find that it’s plenty authentic.
He also has items that are practical for his other hobbies.
Spencer and I like sportcoats but we find a way that works for going out for beers.
A classic menswear uniform but done the way Aleks likes.
My take on the post-pandemic look, but with pieces that are authentic to me.
F.E Castleberry is unabashedly himself and we love the dedication (and the plethora of influences). Everything he does is still on the same spectrum.
An Eli Cash look that he co-opted for himself.
I definitely like to meld my love of milsurp with tailoring.
A tee shirt, done my way, as well as fastening the top button. It’s an experiment, but still feels naturally for me.
My casual style is different yet cohesive than my tailored looks.
Another casual look that brings in what I love about menswear. Outfits like these signal my more creative side.
Jonny is also a great dresser who has an eclectic style and still experiments in a way that appears natural. It also signals that he is a creative.
A basic look, but the details signal Jay’s authentic enjoyment of certain menswear details. He works in Finance but doesn’t dress like a typical drone.

When he doesn’t have a client meeting, Jay dresses quite fun!
A sportcoat, but done practically, in a way that Spencer likes. I’m not sure what journalists typically look like, but at least Spencer makes his own aesthetic.
Movie Directors have no uniform, so they can wear what they want.
A navy cotton suit is another example of blending my taste with a conventional choice.
Of course purple cord is purely driven by how much I love purple (and corduroy).
Getting the most out of your clothing by wearing it with different things is a good way to expand what it means to make a “you” outfit.
My DB has retained its vintage details, which helps provide my POV and authenticity.
Peter’s Menswear Man Vs. Workwear Man illustrates staying true to yourself despite being into two different aesthetics. However if you look closely, you’ll be able to see how they relate to each other.
The rise of the pants are quite similar. Authenticity!
And then sometimes you just gotta be yourself.
Sneakers, but my way.
A good example of my desired silhouette that I’ve stayed true to.
Glenn does a great job of staying true to his love of American trad but done his way (in his brand Junior’s).
My Ascot Chang suit is a contemporary one, but I make it look vintage. Even the use of a checked shirt and striped tie feels more “me”.
A 1960’s inspired look, but more authentically me (with no 60’s pieces).
A slouchy, monochromatic look that is authentic to me.
All the ideas of tailoring I like but done casually.
Michael is a law student and intern, but he finds ways to make his love for trad menswear to come out.
A navy office suit, but in cotton twill.
I knew I liked vintage sportshirts but it took me a while to get into wearing them with modern pieces rather than period clothing.
I wear loafers regularly, but I occasionally wear longwing bluchers. Introspecting on why I like them led to me experimenting with these chunky Tyrolean Yuketens. I’m sure my experience with Wallabees also helped that journey!
Chase illustrating forced versatility by wearing cowboy boots with a neo-trad outfit.
Two different looks but still appears personal and authentic to them.
A casual fit that combines things I like: cotton jackets, vintage sweatshirts, and selvedge jeans.
My interest in ivy got me to try these camp mocs! Might have been weird earlier in my journey, but they make sense now.
Jake is pretty authentic. He’s a shirt maker that dresses for himself.
Damon is a lawyer who dresses corporate, but done his way.
Adam is a film editor who dresses with ivy/milsurp/workwear. Not exactly the look of an editor, but hey, he likes it (and looks good wearing it!).
Shorts done my way.
A merch shirt and sneakers, but done my way.
Scott Fraser has stayed true to authenticity for a long time.
Henrik is an academic who wears pieces that are true to him.
If you dress authentically, even a dog walking fit will still be “you”.
I’m sure many of these pieces were initially hard to get into, but if you know you like it, you’ll find a way to make it work.
Dr. Andre Churchwell is a doctor, but he still dresses like himself. I’m sure some of that is dressing for context, but he knows when and where to do it.
Evening attire, done in a way that we each felt was right.
Cotton suits, two ways.
Two great looks.
I like when lookbooks have a variety of styles and even encourage their shop guys to wear things that they like!
Rob has dressed the same way for a long time. It looks natural, rather than a costume!
Benton works in tech (I think?) and opts to be ivy-trad.
Our styles exude what we like from menswear.
Cody is a hat maker and dresses in tailoring.
Jamie is a photographer and likes wearing menswear, though he does twists to make outfits to his liking.
Chris dresses with authenticity and its clear.
Buzz of the Anthology loves menswear and dresses in a way that evokes classic style and yet a playful demeanor that works for his young age.
Just like Peter, Buzz’s casual style seems removed…until you see the similarities in fit and detail.
Even though he’s a young guy (two years my junior), Buzz still dresses with an obsession for classic menswear. Pretty damn cool!
Even in old age, Hockney still seems to dress with the same themes of slouchy fit and color. That’s pretty authentic to me!

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. We also stream on Twitch and upload the highlights to Youtube.

The Podcast is produced by MJ.

Always a pleasure,

Ethan M. Wong

Big thank you to our top tier Patrons (the SaDCast Fanatics): Austin Malott, Philip Gregard, Audrey Jessica, Shane Curry, Jeremy Osztreicher, and Jarek.

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