On Irony & Subversion


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.

You don’t have to wear this to hang out. You get to wear this!

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.

Ironic, subversive , or both? Either way, I like the fit.

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

The wolf tee is the best example of bad fashion becoming good by sheer irony.
Tiktok kids would kill for this shirt.
The use of tee shirts and tailoring is subversive, but its really rooted in just combining two things you like.
Maybe the irony is in matching metal shirts with luxury garments.
In fact, wearing merch shirts with menswear is the only way I actually get to wear them.
Blazer and Star Wars tee? Yes! Subversive? Sure! Ironic? Maybe to some, but I genuinely love both.
It’s not as ironic when you find pieces that you connect to. Doug prefers Picasso tees instead of other IPs.
“The Ivy Club” cap (worn by Filip) is a fun and definitely a bit ironic, considering ivy has evolved past the style of Ivy League universities in the 1960s to being its own subset of contemporary menswear. I guess that makes it a club!
The Bullshot Book club and its exclusive-but-not-really approach to merch is a fun use of irony.
I remember when people would get upset about untucked shirts.
It was a subversive and defining move of the 2000s.
But they’ve always been a thing!
Is this my own take on Untuckit (which I grew up with) or just doing the 1960s ivy look? Who knows!
Sometimes its just about playing into the desired proportions instead of simply being subversive.
I actually hoped to piss off the untuckit guys with this one.
Normcore! A fashion move today based on “normal” attire from the 1990s.
It’s ironic but also not really, because George always dressed well. ALD seems to have him on the mind.
I know that this is a look but it’s also based on what old people would really wear.
Now it’s a fashion thing!
Maybe it’s just about treating your clothes as “normal”?
Ugly dad sneakers are a big part of “normcore” and are quite subversive to wear with trousers.
It’s subversive to see sneakers with ties, but maybe we just like ties and sneakers?
Bryceland’s “subversive” take on menswear is iconic. Here he wears velvet slippers with hearty selvedge jeans, a western shirt, and blazer.
Wallabees with “dress” trousers isn’t as subversive, but some people don’t like them.
I wear them with worsted suits!
Ties too!
But I do find they look best with knitwear.
It’s subversive to wear black shoes with cotton suits since black is typically reserved for business or formal looks, but I just like the effect.
Cowboy boots with preppy clothing is a bit ironic, especially when the boots are loud!
For Spencer, it’s just about combining what you like: westernwear and ivy.
Chukka boots and tailoring are a milder version of this subversive move.
Espadrilles and a tie might be pushing it.
Speaking of pushing it, Belgian slippers (a house shoe) has become a menswear darling worn with everything from wool trousers to jeans. Talk about high/low (or is it low/high)!
White socks and menswear weren’t always seen as improper.
I do like wearing them with outfits that use ties.
Adam takes it a step further by wearing white socks with sandals. It’s more about comfort here!
Sandals outside of shorts contexts are always going to be subversive to some.
The short suit may be seen as an ironic take on menswear.
But real heads will know that this existed well before Thom Browne.
Was inspired by vintage or doing my own version of Thom Browne?

All this talk about subversion and irony can be traced to Agnelli and the sprezzatura #menswear loves.
The tie tuck is a good example of a lightly subversive move. Some people may find it ironic, I find it practical since most ties are long and I don’t’ like thick knots.
FE Castleberry seems to do an ironic take on preppy menswear, but it does stem from what Fred genuinely enjoys.
I don’t think its completely ironic when it is really a good fit.
A big part of ironic fashion is taking elements out of their original contexts or co-opting those designs for more “fashionable” things. The utility vest is a great example.
I’d count Todd Snyder x L.L Bean a “soft ironic” pair that makes sense.
No one is actually going to fish in these. But you can look like you would!
Rugged “fun pants” with tailoring are a good move too. I have weeks wear I wear these more than my worsted wool trousers!
Military jackets were commonly seen at protests against the very war they were made for.
Then they became worn during protests in general, being quite ironic.
Now, the fact that military jackets are worn with #menswear items like sportshirts and paraboots is even more ironic.
I even like them with a tie (but I love wearing a tie with everything).
ALD is masterclass in lookbook creation with how they combine pieces that don’t make conventional sense but still look cool. That’s fashion!
How about hoodies and tailoring?
Jorts were derided for years…
But tiktokers unironically brought them back (though I do think there’s a bit of irony involved still).
Menswear has always had ironic shoots, like this Drake’s one in the Scottish Highlands. Though perhaps this is what the UK actually wears when next to the sea.
Hats can be ironic….or not (like how Spencer wears the captain hat for a pool day).
Are bucket hats and tailoring ironic?
Big suits can be ironic.
Not exactly the same, but the cut is at least subversive when compared to mainstream suiting.
I definitely think there was a bit of loose irony involved with some of the exaggerated silhouettes of the 1930s.
The 40s definitely loved building up shoulders.
Novelty suits did exist!
The denim tuxedo. A garment brought about by sheer irony that actually is pretty good.
Insert article about the irony of punk rock guys making waves in classic menswear.
The irony of white socks and a beanie with bespoke black tie (complete with dainty opera pumps).
The king of subversive black tie.
Drake’s made a black corduroy tuxedo that looked amazing. Ben even plays into more with a chambray shirt.
Subversive black tie was always a thing…even if some of it only existed in illustrations.
Barbours were used for hunting and now menswear puts them on with crisp navy suits!
I do try to keep a bit of “casual” flair with the OCBD and tweed jacket.
Ethan Newton again going further by wearing a military parka with a sportcoat.
Western shirts with suits and ties is a bit subversive.
Western wear and milsurp…with Alden loafers.
The jacket is the subversive part here!
Adam has never played baseball, but he enjoys wearing this vintage baseball tee in the summer.
Spencer doesn’t work and I am not in the boyscouts, but here we are with our jackets.
Tee shirt and drawstring pants with loafers and a blazer.
Military cap with a blazer and tie? Sure!
Maybe there’s some irony that friends with wildly different fashion tastes are good friends!
Ironic lapel pins from the 1940s. They knew how to have fun back then!
How about the ironic goodness of some vintage ties?
Apparel Arts even wrote about how paint stains are cool!
Sometimes its fun to lean into the absurdity. Like being fully aware you’re dressed like Belloq.
Or going fully 70s.
Or dressing like a Pointdexter.
Or a 1950s tycoon?
A teacher in 1972?
A scout leader?
This is ironic because I’ve never been to Oregon in my life.
Okay this one was definitely a bit too edgy lol.
Absurdity is pretty fun. It’s a different way to entice people to get them “in” on the brand.
That way, they’ll buy anything.

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): Philip, Shane, Austin, Jarek, Henrik , and John.

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