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10 Hipster Fashion Moves That Aren’t Terrible


Brenden Gallagher is a freelance writer and filmmaker in Los Angeles. He writes about television and whatever else seems interesting for Complex.

Image via George Elder for Four Pins

Hipsters have taken a lot of heat in recent years. Since we hit peak Williamsburg in 2005, hipster accessories like suspenders, mason jars, beards, and banjos have grown to become telltale indicators that you’re trying too hard. Whereas hipsters were once viewed as standard bearers of fashion’s cutting edge, these days, the hipster is as tired and mocked as the ’80s Wall Street douche or hippie of the late ’60s. Portlandia has already logged fifty episodes of television sending up hipsterdom and shows no signs of slowing.

Not only has the hipster’s cultural moment passed; hipsters have become cultural pariahs. Ten years ago, the image of the hipster in your mind’s eye was a PBR swilling, fixed gear riding party god, and now the word conjures a bearded thirty-something at the bar by himself talking about when a Pitchfork review “really meant something.” Over the years, hipsters have been guilty of some heinous style sins. We’ve all seen the mustaches that Prussian dukes would find ostentatious and the patterns that even Wes Anderson would dub “a bit twee.”

Despite the hipster backlash, we should admit that some of their trends have had a lasting impact on the culture. What’s more, we should admit that sometimes this influence has been for the better. Here are 10 Hipsters Fashion Moves That Aren’t Terrible.POST CONTINUES BELOW


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In the dark ages between the fall of grunge and the rise of hipsterdom, flannel usage hit an all-time low. While traditional proponents of the fabric like woodsmen and the Amish held strong, there was a dearth of flannel in American style. For a brief, terrible moment, it seemed that work clothes would only be worn by workmen. Thankfully, hipsters fixed all of that. Instead of the billowy, waist-tied shirts that Kurt Cobain once championed, we got slim fit flannels paired with skinny jeans, and the fashion world was all the better for it. Now, flannel has returned to the American fashion mainstream and all is rustic, manly, and right with the world.

Ankle Boots

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In the late ’90s, men’s footwear was very much not on fleek. Chunky skater shoes by Airwalk and Vans fought against those American Eagle boots for space on store shelves. Outside of the odd sneakerhead here or there who actually had respect for what he put on his feet, men’s shoes were in a desperate situation. Hipsters spearheaded the charge towards better footwear by paying particular attention to the various boot options out in the world.

Suede ankle boots, cowboy boots, and old-fashioned work boots came back into vogue as men realized that they could do better than wearing blocky shoes that make you look like a cartoon character. Hipsters helped men pay more attention to their footwear. They did this for the betterment of society. No, they didn’t completely eradicate socks with sandals, but rarely do social movements succeed one hundred percent.

The Casual Blazer

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Hipsters brought college professor chic back into the mainstream. They brought discarded, unloved blazers — blazers with patches and blazers with odd patterns and tweed blazers — back to their rightful place in our closets and hearts. Hipsters recognize that the line between business and casual is grayer than suited up finance bros would have us believe. There are occasions when the business up top, denim party downstairs is the appropriate look. Hipsters know that there is sometimes more of value in your father’s closet that just the family skeletons. The casual blazer gives you an aura of intellectual cool that you just don’t get with any other article of clothing. Just ask Donald Sutherland.

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The hipster obsession with vintage looks has been a mixed blessing to mainstream fashion. Did we really need half a decade of modern men running around dressed as coal miners and Dust Bowl-era farmers? Probably not. But, some vintage looks probably should have never really gone out of style in the first place. Peacoats, for example, contribute to a classic look that is as once masculine and stylish. Some hipsters take the dock worker look too far, adding pipes, nautical hats, and bushy beards in an attempt at full-on sea captain chic, but we can’t let that detract from the dopeness of these coats. 

Image via Fox

The dream of the 1890s shouldn’t be alive anywhere, but certain relics of the past like vests,henley shirts, and peacoats mix well with modern fashion trends. Just leave your straw boater hats, hobo bindles, and Civil War jackets in the past where they belong.

Short-Sleeve Patterned Buttondown Shirts

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Over the last year or so, patterned button-up tees are popping up everywhere, notably from early adopter #menswear brands like Gitman Bros. VintageEngineered Garments, and old hat Hawaiian shirt brands like Reyn Spooner. Now, floral and nautical prints in particular have found their way on the shelves at even the most basic of men’s clothing stores.

Given the sudden glut of these shirts, it’s easy to forget that hipsters dug through Salvation Army racks for tops like these for years. The bold patterned button-up hasn’t enjoyed a revival like it’s seeing right now since the ’80s. Though this look can now be seen on mannequins at the Gap and even Target, it wasn’t long ago that acquiring these shirts required some serious thrift store digging.

Throwback Sportswar

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We’re talking about Starter jackets, varsity jackets, vintage windbreakers, and everything Mitchell and Ness. Hipsters and nostalgia are directly correlated, and minority hipsters in particular have prided themselves on the ability to throw together ’90s-induced fits that would make the Fresh Prince of Bel-Air seethe with jealousy. It’s become all the more easier to find throwback satin varsity jackets or reproduced jerseys from the time when Michael Jordan was the G.O.A.T. basketball player and not a multi-billion dollar brand known for shoes that resell for 700x the price.

Now, brands like Concepts and OVO are having fun with the idea of throwback jerseys, playing Frankenstein with our childhoods and coming up with things like basketball jerseys with hockey team logos, and Palace is using their adidas Originals collaboration to remake the hooligan gear of their youth. There’s never been a better time to dress like a sixth man.POST CONTINUES BELOW

The Man Bag

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In recent years, a man’s bag has become a key accessory. It wasn’t always this way. Before hipsters made messenger bags, man purses, and designer backpacks stylish, all but the most fashion forward stuck either to a boring briefcase or a ratty knapsack. Initially, the trend towards man bags was viewed as feminine, but over time, a solid bag has become a masculine power move. Today, the male bag game has an embarrassment of riches. Each new season brings with it a company that’s trying to change the way we carry out shit from point a to point b. It doesn’t matter what type of bag you like, whether you prefer backpacks, briefcases, saddle bags, or messenger bags. All that matters is that you appreciate that in 2015, the bag makes the man.


Image via Gentry NYC

Perhaps hipsters gentrified your childhood neighborhood, but they have also revitalized the sweater. Ever since Rivers Cuomo, the Ur-Hipster himself, first opened broached the topic with “Undone (The Sweater Song),” men across America have returned to their woolen roots. Sweaters existed before hipsters, but hipsters have done the most for the breadth and depth of the American sweater than anyone since Mr. Rogers.

Cardigans occupy a special place in the hipster’s wardrobe because they are a compromise between the sweater vest, a jacket, and hoodie. It’s the perfect fusion of casual, dressy, and alternative. It’s easy to get a vintage wool one and rock it oversized like Kurt Cobain, or go totally high fashion and get an artisan indigo-dyed patchwork denim masterpiece from Junya Watanabe. The cardigan pairs as well with a plain white tee as it does with a slim buttondown. It’s equal parts nerdy and grandpa-like, and that’s why it’s stood the sartorial test of time.

Vintage T-Shirts

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Lots of progress has been made in the21stt century. We’ve come so far in terms of technology, social issues, and humorous pictures of cats. One area where we haven’t improved is T-shirts. On these digital pages we’ve often discussed what a terrible influence MMA has had on T-shirt culture. The Internet has produced a series of snarky sayings t-shirts that aren’t a great look either. Even shirts from tourist attractions are worse than they used to be. No matter where you go in America, they try to sell you the same shitty looking dad-style tees.

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As a society, we’ve improved many things, but the T-shirt game is simply not one of them. It seems we hit T-shirt perfection sometime between 1978 and 1996, and we’ve been declining towards a dark age ever since. Hipsters were the first to understand that they just don’t make them like they used to. There’s a reason why vintage aficionados like Brian Procell can sell T-shrits like this for upwards of $500:

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It doesn’t matter if it is a 70s band shirt, ’80s NBA Championship tee, or ’90sprofessional wrestling promo tank top,  T-shirts were simply better in the past.  Now, the brilliance of prior decades’ graphic design is influencing modern designers (see Urban Outfitters et al.), but this influence was hard-won after hipsters spent years raiding thrift stores.POST CONTINUES BELOW

Jeans That Fit

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Let’s get one thing straight: Not all “skinny jeans” are technically “skinny.” That term has somehow been applied to the notion of getting jeans that fit and complement your body, which isn’t the same as trying to see how much you can size down in a pair of denim until you look like you’re about to burst out of a pair. There is such a thing as too skinny jeans, especially for hipsters on the wrong side of their late 20s showing off way too much of their … endowment. In fact, recent studies have shown that can actually be harmful to your health.

But before you complain about the tightness of male jeans, I would invite you to remember pants before the rise of hipsters. The ’90s brought us JNCO jeans (which are on their way back, because hipsters). The early 2000s gave rise to boot cut jeans, often with awful fades and pre-worn holes. After years of denim foolishness, hipsters oversaw a sensible denim reformation. Jeans that fit were once again in vogue. Sure, like any partisans, some skinny jean zealots took things too far. But, ask yourself a question: Is male pant fashion better off than it was 10 years ago? Given the dearth of excess fabric hanging in our stores, and the lack of parachute pants in the streets, you have to think that most of us would say yes.