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Your Hipster Style Guide + Outfit Ideas for Alternative Fashion

Last Updated: August 17, 2022

Fashion is a fickle mistress, but there’s no doubt that your relationship with it says something about you. If you want to say a little something more than your average trend follower, you might just be a hipster. 

But what exactly does that mean and how do you dress like one? Going outside of trends doesn’t mean you have to go it alone, and we’ve developed a comprehensive hipster style guide to give you some direction.

What is A Hipster?

In the broadest sense of the word, a hipster is someone who doesn’t follow the mainstream. If your average person’s style is defined by what everyone else is wearing, a hipster’s style is defined by what everyone else isn’t wearing. 

Anything rejected by the mainstream for being too niche, too old, too quirky, or too ugly can be reclaimed by hipsters and transformed into something that represents authenticity and uniqueness

Keep in mind that all this is not to say that hipsters don’t follow trends, they absolutely do. It’s just that these fashion trends occur either outside of or in opposition to the mainstream and function as a part of this particular subculture. 

Since hipster clothing varies pretty widely depending on which trend in the subculture you’re using, we’re going to break this down into a few subcategories of common hipster aesthetics. These are:

  • The Classic Hipster
  • The Beatnik
  • The Pinup
  • The Techie
  • The Kitsch
  • The Bohemian
  • The Creator
  • The Vintage Hipster
  • The Indie
  • The Free Spirited Hipster

Of course, these aren’t the only types of hipster aesthetics out there, but this is a great jumping-off point if you’re interested in alternative styles and ways of living. Let’s get into it!

Hipster Styles

The Classic Hipster

The image of the classic hipster has become so ubiquitous over the years that it’s sort of debatable whether it qualifies as hipster anymore. The “classic” hipster look has actually become so popular over the years that it has ironically fallen into a more mainstream category.

What the classic hipster wears can actually be quite broad, but the general hallmarks are vintage silhouettes, unconventional textiles, and clean lines

If you want to go for a more basic hipster look that’s become popular over the years, think oversized glasses, skinny jeans, and cardigans. 

The Beatnik Hipster

Apologies to anyone who thought they were the original hipster, but your grandparents did it first. Beatniks were the hipsters of the 1950s, defining themselves in opposition to both the suburban conformists and the rock and roll rebels of the decade. 

Prior to a wave of Dior-inspired francophilia in the mainstream, beatniks developed french sensibilities with an academic twist, gathering in Greenwich Village coffee shops to discuss the existentialism of Jean-Paul Sartre and Simone de Beauvoir to the tune of smooth jazz. 

Beatniks were known for berets, breton stripe tops, turtlenecks, and cropped slim leg pants. When you think about a stereotypical image of an artsy French person, that’s what the beatniks were trying to imitate.

The Pinup Hipster

A testament to how ever-changing trends are, this next trend was scoffed at by the beatniks, but picked up by modern hipsters in the mid-2000s. 

As everyone else was clamoring to participate in the burgeoning fast-fashion market, hipsters retreated to vintage (or at least vintage-inspired) shops to get their hands on the poodle skirts and wiggle dresses of the past.

For this particular aesthetic, you’re going to want something with what modern audiences would consider a high waist. After that, you can pick either the full skirt or the pencil skirt that identifies the wiggle dress.

The Techie Hipster

Not every hipster likes to hang out in the past, so this next one we’re going to cover has elements of the future. The techie hipster owes a lot of its style queues to the rise of business casual in Silicon Valley during the 2010s. Mainly a rejection of formal business wear, the techie dresses like it’s casual Friday everyday.

If you want to look like the ultimate techie, throw on a hoodie (preferably a zip-up), some tight jeans, and some practical sneakers. Or, for a dressier style, go for printed socks, a skinny tie, and a latte in hand to complete the look.

The Kitsch Hipster

In lieu of the classically inspired academia that we’re used to associating with the hipster, a kitschier take uses the bright primary and secondary colors that we associate with more modern academia.

The kitschy hipster can rock gaudy, over-the-top, eccentric clothing pieces and make it look good while doing so. Many people consider anything kitschy to be lowbrow or tasteless, but a lot of kitschy hipsters will wear these styles in an ironic sense to make a fashion statement.

Think bold prints, colors, and patterns that don’t really go together but somehow come together to make an outfit into an art piece. 

The Bohemian Hipster

Before Coachella became an annual destination for the likes of Kylie Jenner, bohemian hipsters were embracing the rugged and romantic aesthetic of the late 1960s in a pared down, wearable way.

This can take a couple different routes. The first is the more casual and rugged aesthetic and the second is the more feminine and romantic style. You could say that one evokes the bohemian lifestyle and the other evokes the bohemian spirit.

For a more casual, rugged look, try out some raw, cut-off jeans shorts, leather, fringe, and a dark color palette. A more feminine style would include crochet crop tops, floral prints, and macrame dresses.

The Creator Hipster

This is the type of hipster who hangs out in art museums and always tries to work Van Gogh or Fitzgerald into a conversation. 

They probably have their own Etsy shop, book of poems, or handmade jewelry to show off, and show it off they will. Their style has to be conducive to creating art, so their outfits might not be the most put together. 

A simple dress over chunky boots, a pair of utility overalls and a bandana, or a turtleneck and cuffed jeans are perfect ensembles for this artsy look.

The Vintage Hipster

The vintage hipster’s style is more than vintage-looking pieces or exclusively authentic vintage brands. Although having genuine retro pieces from back in the day really tickles their fancy, they also scour thrift shops for secondhand fashion instead of spending their money on poor quality, fast fashion.

These are the hipsters who make you look bad for giving into trends like crop tops and crocs. Even though vintage-inspired clothing is all the rage these days, a true vintage hipster only has eyes for the real deal.

Their style usually encompasses retro shirts, dad sweaters, color-blocked windbreakers, and basically any other pieces that scream blast from the past. To find vintage and secondhand clothing, search your local thrift stores or check out the best online thrift stores

The Indie Hipster

Before you loved that alternative-turned-mainstream band, the indie hipster followed their Spotify account and knew all their lyrics by heart. They’re the music junkies who wear band t-shirts and actually know who they are. 

If you want to be a *real* indie hipster, you better start researching the bands on your shirts taking up space in your closet. They also have a bit of a grunge look, typically going for darker makeup, deconstructed jeans, and oversized tops. 

The Free Spirited Hipster

Finally, we can’t forget to mention the free spirited hipster who truly embodies a typical hippie. They love nature and reflect this in their clothing in more ways than wearing a “hug a tree” t-shirt.

Today’s free-spirited hipster is into sustainable brands that incorporate natural materials into their wardrobe pieces. They definitely won’t be picking up anything leather, but can be found hunting for organic cotton and Tencel

Although the term “hippie” might bring up images of tie-dye and mandals, a free-spirited style is more comprehensive than that (although I wouldn’t turn down wearing a real flower crown). Think minimalist, eco-friendly, and earthy designs and styles.  

Final Thoughts

It’s important to note that there isn’t a specific way that all hipsters dress, even with these hipster style guidelines above. After all, the term hipster in itself means someone who doesn’t follow mainstream culture and, since that’s always changing, hipster style will always be evolving as well.

There are definitely hipster aesthetics however, each with their own unique and individual style components.

To truly dress in a hipster style, follow the beat of your own drum and get creative. Hipsters aren’t into people-pleasing, especially with their fashion choices. It’s all about defying mainstream culture and fast trends that aren’t here to stay.