15 Hipster Fashion Trends That Are Actually Stylish

Meghan Blalock
15 Hipster Fashion Trends That Are Actually Stylish
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Hipsters as we currently know them emerged in the early 2000s like one messy-on-purpose, fauxhemian hurricane, leaving overturned fixed-gear bicycles, record players, flannel shirts, and SLR cameras in their wake. But hipster fashion didn’t exactly have us at “hello.”

From trending pieces like acid wash denim cutoff shorts to beat-up old T-shirts proudly paraded around as thrift store treasures, the aura of the hipster has long included a tendency toward making the old look new again. So much so that if you head to just about any store in the contemporary market, you can probably find more than your fair share of pieces that are brand-spankin’ new, but were crafted to look old. For that, you can thank the hipster.

MORE: 25 Pairs of Stylish Denim Cutoffs

Their effect on culture (and on Brooklyn, where they pretty much started) has been discussed ad nauseam, but one thing’s for sure: Their mark on fashion has been indelible and undeniable.

We don’t need to go on at length about what hipster style entails—we’re sure you’ve made a joke about it at one point or another—but it is a fact that stores such as Urban Outfitters, American Apparel, and even Topshop have benefited greatly from the trendiness of hipster fashion, selling mass amounts of items like cutoff vintage denim shorts, beanies, and floral headbands to people wanting to replicate the look. Nonetheless, there tends to remain a disconnect between what’s considered cool in the repurposed word of the hipster, and what’s actually considered stylish amongst those who consider themselves purveyors of serious fashion.

MORE: How To Wear Summer Vests

That said, we’ve rounded up 15 hipster fashion trends that are actually stylish—click through the gallery to see what they are and how to wear them!

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When worn correctly, flannel can be incredibly stylish. The key is to not rock a hugely oversized man's flannel shirt, which tend to be too big in the shoulders and long in the arms. Instead, choose a more fitted cut, unbuttoned at the top to show a bit of skin, and sleeves rolled up to mid-forearm or elbow. Of course, you can't let your hipster status get away too much, so pairing your flannel with '70-style high-waisted jeans is okay in our book. 

Image via Orchid Grey

The Headband.

The flower crown is a staple in
the hipster closet, recalling music festivals and other sun-frolicking activities. For a chicer take on the trend, try a
solid turband or head scarf, and pair it with a muted day dress and heels.

Image via Do the Hotpants

Photo: Pinterest.com/ampsalms

The Crop Top.

There's definitely a wrong way to wear a crop top, so a good rule of thumb is this: the lower the waist on your pants, the longer the top should be. In other words, a really short crop top deserves a more high-waisted pant, and a lower-waisted pant (as seen here) needs a bit of a longer top.

Image via The Berry

The Wide-Brimmed Hat.

For this most ubiquitous of hipster fashion trends, the key is to stay classic: Stick to an all-black hat, or (at most) one that is a solid, dark color with a contrasting stripe around the bowl. Steer clear of wild colors and vivid patterns, unless you intend the hat to become your only statement accessory.

Image via Electrix Fashion

The Collar.

Shirts with buttoned-up collars are the cornerstone of the hipster penchant for the girls-wearing-boy-clothes look. The contrasting collar has now become more mainstream, so for maximum chicness, stick to light on dark or dark on light.

Image via Orang Free

The Thick-Framed Glasses.
Any hipster worth their salt rocks a pair of Buddy Holly-style frames (whether they need 'em or not), but when they're not paired with an excess of flannel. beanies, and skinny jeans, they can look quite stylish, as evidenced by J. Crew honcho Jenna Lyons, who wears hers with everything. 

Photo: Stephen Lovekin/Getty Images

Southwestern-Inspired Jewelry and Accessories.

From heavy metals to copper-toned baubles, a flavor of the Southwest is no stranger to hipster style. Wearing just one piece at a time might seem a bit out of place, so try stacking the bracelets and rings and maybe even a necklace for maximum effectiveness.

Image via 2 Bandits

The Overall.

One of the most divisive of the hipster
fashion trends, the overall can indeed be chic. Stick to classic denim washes and fitted styles, and be sure to
wear a pair of low heels or flats.

Image via From Paris to London

The Oversized Sweater.

Hipsters love baggy clothes, and the most well-loved of the baggies is probably the grandpa sweater. For a stylish take on the trend, try wearing the fall essential so big that you don't need pants, then pair it with a set of sleek pumps and a slouchy bag.

Image via Galeene

Giant Round Sunglasses.

Oversized round shades are another hipster staple. In order to avoid looking more kitschy than chic, avoid frames in tribal prints, neon colors, and other loud patterns, sticking instead to classic white, black, or tortoiseshell frames.

Image via The Berry

Ripped Jeans.

Speaking of the love for baggy, nothing gets more love in a hipster closet than ripped boyfriend jeans. The key is to not get too baggy with your look, pairing the pants with a basic tee, sleek blouse or and blazer, and a solid pair of booties.

Image via Serve Me Now

The SLR Camera.

Whether a trained photographer or not, a good hipster always carries her camera with her when hitting the streets. Camera-as-accessory is a distinctly hipster fashion phenomenon, and especially useful during Fashion Week.

Image via Elle

The Chambray.

A button-up in this lightweight, pale denim fabric is a necessity, and looks super-stylish with a pair of lace shorts and a set of low-heeled lace-up Oxfords.

Image via Holly Dolly

The Patterened Jean.

Flower-splattered jeans, especially of the faded variety, are to be worn with a casual, solid-patterned shirt (see: Chambray), a good pair of shades, and a sleek pair of heels or sandals.

Image via We Heart It

The Vest.

The cropped vest is one of the most easily re-purposed accessories in the hipster catalog. It can stylishly be worn with a cute sundress, a crop top and shorts, or a T-shirt that's tied at the waist with a flouncy skirt.

Image via Obaz

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