How to Dress Like a Hipster

The “Hipster” moniker has taken on so many different stereotypes over the years, that it has been relegated back to it’s most simple form: a purveyor of hip culture. It’s no longer headbands and American Apparel hoodies circa 2009. It’s not looking like a Mumford & Sons video extra. It’s not even those who don ironic mustaches and tees.

Today’s hipster is on the pulse, a smart balance of old and new, but even when rocking vintage, always fashionably forging forward. We may have grown up and out of the label, but a new crop is continuously morphing and multiplying after us. Read on to identify and imitate the contemporary counterpart to your own old phase.

Here’s How to Dress Like a Hipster

Steeped in cutting edge culture, the term will always demand being on the forefront of trends. As fashionistas who have been around the block, we know these trends tend to recycle, so it’s no surprise you’ve probably seen a few of these favorites before. Today’s version of the classification is full of 90s kids, meaning plenty of nods to childhood nostalgia. Unlike previous generations who looked to 60s dresses and 70s band tees to fuel and fill their closets, the current Hipster is having a moment with a playful amalgamation of all of the things of their past: sportswear, Seinfeld norm core, club kid, you name it.



Streetwear graphic tees meets jerseys meets plastered sleeves, backs and everything in between. Brand names, tag lines and establishment dates purposely filling as much space as possible pokes a healthy dose of fun at the 90s kids’ affinity for capitalism and corporate culture.  Think Miley, think UNIF, think sports teams.



Where today’s male Hipster would be rocking a cuffed khaki trouser, the girl’s are on a higher fashion tip, with the replay of a billowy gaucho. Preferably paired with a platform sandal or slide and some type of cropped top/sports bra combo, this seemingly questionable style is already picking up steam circa bloggers. Play with proportions, it’s fun, we promise.

Bomber Jackets

Bomber Jackets

Draped over the shoulders or potentially buttoned up top, the bomber jacket-as-cape look works for either gender, providing an equally sporty or classic topper to any combination of layering pieces. If it gets too hot, you can tie it around your waist in replacement of the infamous Hipster flannel.



Shoe-wise, it’s all about the slide. Pumped up with a platform, played down with a Birkenstock or full-blown activwear with a Nike slip-on sandal, the Hipster footwear of choice is all about the easy-breezy. Extra credit: Bucket hats. RiRi’s way ahead of you.


Melissa is creative communication professional with 9+ years of experience writing for the beauty and fashion industries.