# Stylish Tips on How to Dress Like a Hipster

Hipster wearing a black hoodie jacket is sitting at the center of rail road

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If you’re going to upgrade your personal style, you might as well take the plunge and finally get around to learning how to dress like a hipster. Learning how to achieve the hipster look is peak millennial culture, but let’s be real – actually dressing like a hipster takes some guts, and pulling it off well takes a little effort. For both men and women, learning how to dress like a hipster is one part learning fashion trends and two parts being bold enough to walk out the door with confidence. But don’t worry, learning to dress like a hipster is mostly about attitude.

What Is a Hipster?

What is a hipster? Honestly, finding a perfect definition of a hipster is difficult, especially since hipsters are sometimes the butt of pointed jokes about millennials who are trying too hard. Individuality is the root of hipster culture, but it has occasionally been appropriated in a way that leaves us with a “hipster standard” that is just as conformist as any other style. Aside from the traditional definition, there are a few things that make a true hipster – including hipster attitude, hipster habits, and hipster individualism.

Hipster Definition

Oxford dictionary defines a hipster as “someone who follows the latest trends, especially those outside of mainstream culture.” Others add onto this definition by saying that hipsters are a subculture that both is and isn’t part of the mainstream culture. Hipsters are basically on the cutting edge of whatever the mainstream culture is at the time. Essentially, hipsters are extremely hip.

For example, hipsters have been infamous for their love of artsy coffee shops. First, they patronized Starbucks and made it mainstream. Now Starbucks is the mainstream culture, so privately owned coffee shops are frequented by hipsters because they are unique. These coffee shops are common hipster stomping grounds these days, whereas Starbucks is regarded as being so mainstream it’s almost “tasteless” to visit one if you think of yourself as a “true hipster.”

Another good example of how hipsters lead mainstream culture through subculture is men’s beards. When hipsters first began creating a subculture, hipster men began growing out their beards because the mainstream trend at the time was a smooth-shaven face. Hipsters created the beard trend that has now been adopted by the mainstream so thoroughly that there’s even Movember: a month dedicated to growing beards as a way to bring awareness to prostate cancer.

Hipster Attitude

What is hipster attitude? Confidence is a big part of being a hipster. Hipsters do what they want without any care to how they are judged by the mainstream (or at least what they perceive to be mainstream). To be a hipster, you have to embrace an attitude that will allow you to be yourself with your head held high.

Hipsters shun the mainstream. They like different music, wear different clothes, and eat different foods than most of their demographic. However, hipsters can sometimes get so caught up in shunning the mainstream that they end up forcing themselves to like things they don’t actually like and conform to a kind of “hipster” standard. For a hipster, it’s a slippery slope.

Hipster Habits

Hipsters like to call themselves ironic. The whole point of hipster subculture is to undermine set expectations of how people should be or what people should like. Hipsters have a habit of trying new trends simply because they can and because people might not expect them to. Common hipster habits in recent years include drinking craft beer, putting avocado and kale on everything, and adopting traditions from other cultures. Hipsters like to do the unexpected.

Some hipsters also tend to adopt new trends and then drop them once they’re too mainstream – chunky black glasses are a good example of this, as many hipsters now embrace wire or tortoise-shell glasses instead.

Hipster Individualism

At the end of the day, being a true hipster is all about individualism. Hipsters do what they want and hipsters like what they like. Hipsters are unapologetic about this dedication to individualism, which is actually very freeing. Being a hipster is about being able to express yourself without apology – you are who you are and that’s the end of it.

But this is another slippery slope, some hipsters get so caught up in being “unique” that they view those in the mainstream as being inferior to themselves, which actually goes against the grain of hipster attitude. Any expression of individualism, whether or not that individualism is subculture or mainstream, should be respected by hipsters. Hipsters value independent thinking above all else.

The Evolution of Hipster Fashion

Hipsters have always been around. We can actually trace the word hipster back to the 1930’s, where a hipster was defined as a jazz dancer. Over time, the term hipster has also referred to the hip-hugging pants popular in the 1960’s and the 1970’s. Why does this little history lesson matter when we’re talking about the contemporary hipster? Because over the last decade, hipster fashion has changed in a big way. Before you learn how to dress like a hipster, you should probably know how hipsters used to dress.

Yesteryear’s Hipster

Contemporary hipsters first emerged around 2003 in a haze of plaid shirts, thick glasses, and beat up Converse shoes. Yesteryear’s hipster made a point to take ironic risks in fashion, usually by wearing graphic tees that had witty phrases on them. By the time 2009 came around, hipsters were responsible for popularizing the lumberjack look of overgrown beard, overlarge plaid shirt, and usually some kind of knit beanie.

Hipsters of yesteryear are also responsible for making chunky black glasses popular and for making it okay to wear scarves indoors even during warmer months. The fashion of the yesteryear hipster was laid back and almost-grunge; a way to counter the popular fashion of that time, which was an ultra sleek, clean-cut preppy style or an ultra-sweet, bubble-gum pop sparkle.

Today’s Hipster

The hipsters of today are a bit of a different beast. While the beards and windswept haircuts haven’t gone anywhere, today’s hipsters have taken a turn from grunge-genre fashion and have found inspiration in vintage trends. Casual-smart dress with an unexpected twist is the calling card of hipsters in the current day – we’re talking suspenders attached to jeans, the return of velvet and satin, and a resurgence of overalls.

Hipsters of today have also adopted new hairstyles, new music, new foods, and other new counters to what is “accepted” in the mainstream culture. But the hipsters of today have aged into their hipster lifestyle, which means that there is something a little elevated about the overall style

How to Dress Like a Hipster

Now that you’ve been primed on how to act like a hipster, it’s time to finally get down to the business of learning how to dress like a hipster. Fortunately, learning how to dress like a hipster is easier than you might think. Just remember that learning how to dress like a hipster is a head to toe commitment.


Take a page out of retro fashion and frequent vintage shops or thrift stores to update your wardrobe. When you’re looking for vintage fashion or vintage-inspired fashion, you want to be looking for patterns and clothing cuts that were popular in the counterculture of the 1960’s, 1970’s, and the 1980’s. For pants, vintage means high-waisted jeans, hip-huggers, hipped skinnies, patchwork or embroidered jeans, and even wide-leg or bellbottoms jeans.

For tops, you’ll want to look for anything highly patterned or bohemian-inspired. You might be able to use vintage colors, like mustard yellow, burnt orange, and other muted shades, and look for different fabrics, like velvet or corduroy to help achieve this look. Using vintage accessories, like belts, bags, and hats, is also a good way to incorporate vintage into your wardrobe.

Modern Mix

Hipster fashion can be achieved by mixing and matching modern clothes with vintage or vintage-inspired pieces. Go ahead and pair your ultra skinny jeans with a loosely-tucked floral shirt from the 70’s, top it with a beanie, and finish it off with Doc Martens that somehow survived the 90’s. Mixing your modern with your vintage means not being overly coordinated – things should go together, but they shouldn’t match. An easy way to do this is to combine different patterns that have a common base shade in common – such as using the navy background in your shirt to tie into the navy lines of your checkered tweed jacket.


Hipsters love a good graphic tee. Whether your graphic t-shirt features your favorite childhood cartoon or a witticism or a political campaign slogan that’s three election cycles old is up to you. The point, though, is that you want to combine your graphic shirt with something that counters its casualness. Add in suspenders or wear the shirt with nicer pants or beneath a structured jacket. You can always layer your graphic shirt with plaid or another patterned shirt if you really are feeling casual.


Hipsters made chunky black glasses with square frames a thing; but for most hipsters, that trend has long expired. However, if you still need glasses because without them you’re as blind as a bat, you might want to look into updating your frames. This is another time where you can borrow from vintage fashion. Hipsters love a good retro frame for both glasses and sunglasses. If you don’t need glasses to see, you can always opt for empty frames or blue-light canceling glasses in a retro shape.


Lately, hipsters have truly embraced hair dye in a big way. Any color of the rainbow is acceptable, for both men and women. For actual haircuts, undercuts, buns, and highly layered styles are good options. Hair is just another form of expression for hipsters and anything goes as long as you like it.


selective focus photography of woman sitting on Volkswagen Beetle parked on beach shore

Photo by Amos Bar-Zeev on Unsplash

If you want to know how to dress like a hipster, all you really need to know if how to dress like yourself. The entire point of being a hipster is being comfortable to be yourself, whether you are trying new trends or borrowing vintage ones. As a member of the modern counter culture, hipsters do what they want and like what they like. There is no “wrong” way to be a hipster as long as you’re expressing yourself honestly as an individual.

Featured Image by Foundry Co from Pixabay

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