As I reflect on what I’ve written (and podcasted) about during this past year, it seems clear that my essays are inching toward understand the “why” behind dressing. Obviously, wearing clothes as a hobby is not a fine art but like photography or tinkering at the piano, creative expression is still at play. And with such activities, discussions of societal intent and effect are bound to arise, especially in a no-context world where it seems that anything in fashion can go.
With fashion’s democratization and use as a hobby, it opens itself up to rebranding, changing clothing from being functional (aka to not be naked) to present personal commentary. For my purposes, commentary is positive— I wear clothes to show that I like certain things, whether it’s through merch or design details like spearpoint collars. But what about when we want to spin fashion on its head? What if we want a bit of irony and subversion: two very loaded loaded terms are admittedly very confusing (and subjective).
Please remember these are my opinions and are definitely not applicable in every case. I’m just trying to define how I use differentiate these terms for the sake of my blog and podcast.

Irony typically refers to an IFYKYK relationship between the wearer and the viewer of clothing, where the intent is usually the opposite from what you’re presenting. High fashion and designer brands like Balenciaga are typically the poster children of Ironic fashion, as they have been at the forefront of pushing the boundaries of both fashion and anti-fashion with intentionally “ugly” pieces and collaborations with video games and animated shows. It goes against convention, with everything being apart of some sort of “joke” that only a certain crowd will get. Sometimes entire “bad” fits are still “good” simply by the effect of being “bad” and that luxury can be friendly with mainstream pop culture— even if it’s just for the memes.
I’ll admit that I don’t actually mind the confusing nature of ironic fashion. In fact, I appreciate irony/subversion more the deeper I get into describing menswear as an aesthetic hobby instead of a “correct” form of dress. It may not be my thing, but someone else may like it (it’s all a matter of personal taste after all). I also do find humor in absurdity and “intentionally bad things”, which is why I’m a huge fan of Scott Aukerman and Comedy Bang Bang. It definitely involves a bit of exclusivity involved where only the people “who get it, get it”. This feature may even get you to like it even more.
Classic menswear is not immune to irony, though it’s obviously diluted and altered to reference it’s storied past as the lingua franca of clothing. It may not be wholly intentionally “bad” (like a Triple S) or weird (like chainmail tops) but menswear does try. Obviously some lookbooks and shoots do hinge on being “fashiony”. There’s also the whole fake merch trend that is still going on through Drake’s and Rowing Blazers, allowing suited dudes to get their streetwear jimmies off while remaining firmly in #menswear. We can’t forget about terry cloth blazers, fake crests, or a plaid tweed based on an infamous aperitif. There’s definitely a joke and in-crowd involved, though it hinges less on being “bad on purpose” and being more about “soft” irony and self referential humor.
Subversion is slightly different, in that I see it as a vehicle for styling or design choices. It can contribute to irony, but that’s not always the case. There is a whole myriad of things that can be considered subversive: a suit in cotton drill that isn’t a chore coat style, wearing a denim western shirt with a tie, or wearing white socks with loafers…and dress trousers rather than jeans or chinos. Most of these actions act to take down the formal connotations of menswear, which is why subversion (in my eyes) tends to break hierarchical tradition in clothing conventions and punch up instead of just subversion for subversion’s sake. This is why subversive styling is quite common in contemporary classic menswear— it’s a way to keep the genre “fresh”.
Both of these qualities seem to be quite common in our circles as the menswear industry tries to stay relevant (or at least be seen as attractive) to contemporary fashion enthusiasts. But with the current “no-context” conditions and the fact that irony is becoming overplayed even in general fashion, will menswear become just as lost? If anything goes, then everything should go right? What’s to stop us from going overboard with absurdity? Would we not lose what makes menswear, menswear? Won’t irony lose it’s effect the more others become “in the know”? Isn’t subversion lost the more common it is?
One major critique of irony in mainstream fashion is that it becomes a tool in defensive dressing. Ironic outfits are meant to mask your true intentions and only signal to others in the know; it also defends “bad” as “good”, allowing you to [seemingly] get away with anything under that excuse. In other words, “you can’t critique me because I actually don’t really care”. While this can be admired from an artistic perspective (as well as just a thick skin), I find issue with this mainly because I approach menswear with more of a celebratory (read: fanboy) mindset. In other words, I think that you should always wear what you like!
Derek even hinted at this in his own essay on irony four years ago. He talks about gag gifts and how at a certain point, a gag is not a replacement for intent. Instead, he calls for a return to sincerity, which is a much stronger root not just in clothing, but in all forms of expression: “films, art, and even social relationships.” It’s good to be authentic even if it can be a challenge to be yourself for others to perceive; perhaps that’s why most people I know have no issue with standing out.
That’s where irony and subversion get to come into play. Like with cool or [perceived] effortlessness, irony shouldn’t be the only reasons for dressing, but rather an additive that makes the “statement” of your fit more interesting. Things become ironic or subversive because of your context and preferences, not just based on society, whether we’re referring to the mainstream of even the niche subcultures of menswear. Trying to dress strictly for irony just seems exhausting and even worse, doesn’t really signal what you genuinely enjoy.
I also think that menswear, at least in its current form, is inherently ironic. There is no “real” reason for us to wear neck ties, lace-up leather shoes, or even lapeled jackets but we do it anyway because we like it. It’s also funny that garments that used to be seen as everyday wear has now been relegated to only the most conservative or formal of environments. Garments are now closer to luxury goods; this is especially true for ties!
Irony can also change based on your context. For some guys, like east coast teachers or finance guys, wearing classic menswear makes sense. In my life (as well as for many of my friends), it’s definitely more ironic. I have moved away from my accounting and menswear background into a totally new industry, but I still love wearing a jacket and tie…even when I’m working at home where no one but me sees what I’m wearing. How about enjoying ivy style despite me (or my family) never even being around such universities? Or being inspired by vintage clothing despite not having a fancy grandpa who wore 3PC suits? Can’t forget collecting milsurp while being critical of the US armed forces and decades of imperialism. I’m not even speaking about myself; all of my friends have a bit of irony that comes with their enjoyment of classic menswear, which only compounds when you consider the places where we hang out (life doesn’t have a dress code). It’s why putting outfits together is best described as cinematic dressing, where leaning into a character or standing out is all apart of the fun.
Subversion is also an empowering tool as well. It’s a specific way to get at what you like and break convention—to dive deep into what interests you and incorporate it into something else. Like I said earlier, subversion is about punching up and because menswear is built on old rules, it’s ripe for a bit of rebellion. For example, one could like wearing suits but not be into stiff poplin shirts. A subversive move would be to wear “formal” worsted suit with a “casual” oxford shirt; this thought process leads to why workshirts and westerners is popular to wear with tailoring (and even with a tie). It doesn’t stop there: subversion in menswear has lead to adding in sneakers, bucket hats, and merch tees with suits. How about mixing in milsurp or wearing fun pants? We also can’t forget the intentional nods to vintage style when menswear was originally built on being classic and rather “agnostic”. These moves all include things people have liked because they liked it and decided to add it into trad menswear. You might even say that current menswear is built on canonizing subversive moves.
The question then becomes if this this still considered subversive if #menswear is filled with such examples. I’d say no! Hell, menswear today is full of experimentation and “new” contexts for pieces. This happened before the Pandemic; if you look at the niche members of #menswear, you’ll see that these “subversive” moves were always around. Hell, I consider Ametora’s recounting of how Japan adopted and transformed “American ivy/trad style” to be a great example of irony in menswear. All of this discussion about irony and subversion might just be a discussion on “why” trends and specific garments are viewed as attractive and why they come in and out of the zeitgeist.
That’s the thing: subversion, like irony, is subjective and dependent on context. I still find white socks subversive, because I still get random comments from people (both IRL and online) about how that’s improper; the same thing happens when I tuck my tie or when I put my hands in my pockets. Like with “cool“, these moves are obviously still subversive within individual historical contexts and for mainstream audiences, but if we’re looking at subversion in terms of the amount of people doing the move, it doesn’t really pass muster. But that’s not really the point, is it?
Dressing completely for the sake of irony and subversion, even in a classic menswear “context”, seems completely exhausting. It means that you need to keep up with everything in order to ensure your moves aren’t diluted by the audience wising up to your moves; you’ll also need to make sure you’re constantly looking for new ways to be ironic and subversive. That might work for some people, it isn’t just for me.
I don’t really care if the “irony” of menswear is being lessened. It’s simply not the primary reason I get dressed. I don’t deny that some of the choices can be new and subversive (for me and to others), but I primarily like to wear things because I like them. For example, wearing western shirt with a DB suit may be subversive, but I can also like it for the merit of those items instead of just for subversion’s sake. I’m not here to shock people! I didn’t get into vintage just to rebel against slim fit; I did it because I liked the silhouette. Sure, it may have been fun to go against the #menswear tumblr grain, but it was a side effect of me getting deeper into what I truly wanted to wear.
Good dressing to me is about self expression. Like with cool or effort, an ironic or subversive effect comes as a bonus instead of being the primary reason. In fact, I’d rather get to a place where moves don’t have to be considered ironic or subversive but authentic: we do these things or wear these garments because we like them. If all of these moves truly become common place, that’s fine by me. In fact, I want that to happen!
A lot of this blog has been about demystifying some of these “subversive” menswear moves. Not just by giving historical precedent (to show you it’s not exactly new) but to show that other people do it too. it may not be a move you ultimately decide to keep in your “style arsenal” (ugh), but my hope is that you get a better appreciation for why it happens and why others choose to do it. Most of the time, the answer is that we just think it’s cool. Over time, subversive things become familiar, and the amount of “effort” involved becomes miniscule. It’s no surprise that my style truly has gotten “safer” and expected (dare I say, repetitive) despite having been built on “new” things. The thing is, they were new for me.
Anyway, we discuss irony and subversion on the podcast below, diving deep into how these terms apply to our menswear hobby. Maybe it’s ironic for a podcast and blog who claim to be without “stuffiness” to think so hard about subversion, but hey, that’s life! Life is ironic. It ain’t that serious.
Of course, that’s not to say that we discount viewer’s responses completely or actively refrain from pushing conversations, but that’s a topic for another time.
Podcast Outline
- 07:53 – Topic Intro
- 10:12 – Defining Ironic/Subversive Fashion
- 20:13 – Die, Workwear! On Ironic Fashion
- 25:59 – Sprezzatura is Ironic
- 30:24 – Irony as Empowerment/Rebellion
- 43:40 – Our Execution of Subversion
- 1:02:03 – Wrap-Up
Recommended Reading
- Fashion’s Spencer’s Gifts Moment by Die, Workwear
- The Irony of Ironic Fashion – Dukeform
- Our favorite subversive moves (that aren’t that subversive anymore):














































































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The Podcast is produced by MJ.
Always a pleasure,
Big thank you to our top tier Patrons (the SaDCast Fanatics): Philip, Shane, Austin, Jarek, Henrik , and John.
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