From Swag To Drip: How Memes Have Shaped The Way We View Men's Fashion

When we think about what our all-time most memorable memes are, it’s unlikely that the focus is on what their protagonists were wearing (if they even wear clothes at all). Yet, there is a storied history behind the fashion in certain memes that goes above and beyond what is expected of them.

Some of the most legendary images ever distributed online were propelled to fame due to their fashion sense. If you can break it down into a starter pack just by looking at it, you know it’s made more of an impact than you might expect — as the era-defining examples here show us.

Scumbag Steve (2011)

Summary: Patron saint of small-town losers.

For a dedicated slacker, Scumbag Steve was a lot of things to a lot of people. This infamous photo of Blake Boston came to represent everyone from the mooch in your friend group to your douchebag former classmate who you may or may not cross the street to avoid.

He could never have carried such a heavy burden without a look to remember, one which was as offensive as it was bland. His all brown, fur-lined ensemble was versatile enough to front a MySpace album cover and a complaint about people who put their feet on your seat at the movies. This was what flamboyant meant when you were a complete dick in every single situation.

His no-good attitude was epitomized in the jauntily angled hat, which took on a life of its own as a spinoff meme that shamed everyone from politicians to your pet cat. It even inspired a quest to find the exact brand of Red Sox cap that had taken over image macros everywhere. Ironically, it turned out to be pretty rare.

The Fedora (2012)

Summary: M’lady. Tips Fedora

Whether it was because it made easy photoshopping or the symbolism was too irresistible to ignore, headgear ruled as the accessory to pick on when it came to memes in the early 2010s. This style of the hat had been mocked since it had begun to experience a style renaissance in the late '90s when people began to suggest that wearing one did not in fact turn you into a Humphrey Bogart lookalike.

When it really hit its stride as a meme though was in the golden age of Tumblr. It came to represent an approach to life completely at odds with the notoriously progressive platform, and the single-topic hate blogs were there to prove it.

The average fedora wearer was strongly associated with white knighting, anime and overzealous atheism and usually packaged with a neckbeard or perhaps a samurai sword if he was particularly theatrical. This was the sadsack loser that had haunted the internet since forever in a different costume.

Unlike the rest of the memes on this list, the fedora was not associated completely with any one individual. It acted as a signifier instead, a way of showing up every proto-incel or racist weeaboo that refused to develop more self-awareness. Sometimes, it was just a way of dunking on a nerd you didn’t like who was probably ugly anyway.

You didn’t even have to show your face to be crowned with a fedora-wearing status, so easily was it implied. A prime example was everyone’s favorite piece of atheist philosophy, In This Moment, I Am Euphoric. Offering classic Reddit cringe, it was referenced on many a fedora-donning meme. This hat was something you earned as much as it was an accessory you chose to wear. And no, I’m not a professional "quote-maker."

You Know I Had To Do It To Em (2017)

Summary: Not all kings wear crowns.

"Iconic" is a word that gets thrown around the internet a lot these days, but if anyone is deserving of this adjective, it’s Twitter user LuckyLuciano17. Never before had a flex failed upwards with such spectacular beauty as when he shared his most famous image on social media.

You Know I Had To Do It To Em was, in essence, an OOTD post gone wrong. Naturally, this meant it was all about the look. His bold, color-blocked outfit was as if Scumbag Steve cheered up and went outside, and the flashy watch and boat shoe combination screamed wannabe status symbol.

If this meme is defined by anything though, it’s the pose. The elusive "it" that so many have speculated on was brought by his clasped hands and slightly too far apart feet, which numerous spinoffs have paid homage to.

As the most avid Luciano fans know, the image debuted on Instagram before its legendary Twitter outing, with the caption "Real men wear pink." Perhaps the photo was meant as a commentary on the often limiting boundaries of men’s fashion trends?

Whatever the reason, it was vital enough to make a guy posing on the sidewalk become an overnight thesis on how to shitpost about modern masculinity — and that would never have happened if he had had a less prominent sock tan.

Doomer (2018)

Summary: If depression was a Halloween costume.

Wojak was not a fan of clothing before the Oomer Wojaks came along. If anything, he was defined by his complete blankness that enabled memers to project whatever they felt like onto him.

When the Doomer arrived on the scene, he represented an official upgrade to the dress-up doll, with a fashion sense that was a lot darker than any of his MS Paint predecessors. With a lot of his original comics focused on his inability to win over the Doomer Girl, his basic drip arguably took some inspiration from the virgin in Virgin vs. Chad. He also did his best to bring the hat back into the meme discourse, although it’s more a means to hide from the world than a comment on the person wearing it.

The cherry on top is his omnipresent cigarette. At a time when all the Zoomers had moved onto Juuling, he was damned to be part of the last generation to think smoking is cool. It was a difficult task to make Wojak more angsty than he was to begin with, but the Doomer made a success of it.

Bernie Sanders In A Chair (2021)

Summary: Grandpa has had enough of your political agenda for one lifetime.

If 2016 kickstarted the Bernie Bro meme machine, then the 2020 campaign trail secured his place in meme history across an even wider part of the political spectrum. People marveled at his living room having a chair dedicated to laundry and his fundraising plea became one of the most recognizable image macros of the election.

However, it was not until Joe Biden’s inauguration that Sanders secured his place in the fashion hall of fame. His outfit suggested he had errands to run after the swearing-in of the 46th president. It was quickly realized that he wore the very same coat featured in I’m Once Again Asking For Your Financial Support because so many great memes are built on outfit repeaters. Meanwhile, the mittens brought the wholesome novelty factor, knitted by a teacher as a campaign trail gift.

As with Lucky Luciano, the key to its success was all in the stance. Hunched over in the cold, Sanders’s posture was, according to some, more comparable to waiting for his wife at the department store than celebrating the incoming president. Of course, it is exactly this everyman quality that makes for a memetic style icon: the cool factor isn’t necessary when you have an attitude that makes up for it.

These looks may not be high fashion, but their ambitions are almost as big. Each meme here is emblematic of a different phase in meme culture because its main character distills so much through how they are dressed. Memes aren’t likely to take over from influencers when it comes to stealing their style, but they can be one of their most powerful critics. It’s not about the fit, it’s who is wearing it.

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