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100 Cool Hipster Outfit Inspirations for Your Next Street Look

Hipster fashion has a great impact on street style and pop culture—think of distressed jeans, acid washed cutoff shorts, flannel shirts, combat boots, vintage denim, beanies, and motorcycle jackets. If you want to inject some edgy yet effortless vibe to your wardrobe, draw inspiration from hipster fashion. A great thing, with a few styling tricks, you can make the old look new again. So, keep on reading for the 100 cool hipster outfit inspirations for your next street look.

What is Hipster Fashion?

Hipsters are known for rejecting mainstream fashion, for where they dress the way they want without the influence of culture and trends. According to experts, hipster outfits are the result of expressing one’s idea of fashion regardless of the style rules and trends. Also, hipsters are not afraid of mixing and matching their wardrobe staples, layering their most favorite pieces and even experimenting with accessories to create a certain look.

If your music interests and fashion choices fall outside the mainstream, then you’re probably a hipster who loves hipster outfits. Most likely, you also have an alternative lifestyle since hipsters reject the established culture. However, hipster outfits look pretty basic—think of cargo pants, beanies, denim jeans, vintage tee, distressed cutoffs, flannel tops, leather jackets, and such.

Yes, hipsters deeply influenced culture, fashion, and music. Most of the time, hipster outfits are associated with people who loves modern rock, and alternative music. If you love a polished, classy style, then, you’ll find hipster outfits not so appealing. If you usually buy clothes from fast fashion stores and high end shops, hipsters go for vintage and thrift stores.

Unfortunately, there are some negative connotations associated with hipster outfits. In fact, most hipsters were featured on films and television screens, and they were not the good guy of the story. A great thing, hipster fashion is broader nowadays as you can still have your typical office job wearing suits on weekdays and sporting hipster outfits on the weekends.

Brief History of Hipster Fashion—and Modern Street Style

Do you know that the term hipster is actually translated as “up to date” in the 1940s? In fact, hipster outfits are known for the traditional outfits of jazz musicians and fans. Nowadays, hipster outfits might sound dated since they are associated with the jazz musicians in the 1920s. In the modern times, you’ll see the typical Londoners and New Yorkers wearing hipster outfits. But still, the street style and hipster outfits won’t define the country or city itself.

In fact, there are different versions of hipster fashion and outfits. While some cities define hipster outfits as rugged outdoor-as-indoor look, others go for grunge and bohemian inspired fashion. In Russia, hipster outfits meant thick soled shoes, bright colored outfits, and vintage clothing.  In fashion, everything evolves and hipster outfits became known in low-slung pants in the 1960s and bohemian-inspired touches in the 1990s.

More than that, hipster outfits became associated with the hippie look during the Vietnam War in the 1960s and grunge look in the 1990s. Until the 21st century, The New York Times used the term “bohemians” to replace the term hipster, and Time Out New York publication referred them as the “arty East Village types”. In fact, the hipster fashion is more associated with having a different look rather than copying what’s your style icon or television star is wearing.

If you want to dig deeper into hipster fashion and create hipster outfits of a certain era, let’s travel back in time. In the 1940s, men and women were inspired to channel the jazz music culture through their clothes. Have you been a fan of Emo music and pop-punk bands—Fall Out Boys and Green Day—in the 2000s? You might sported band tees, hoodies, flannel shirts, and Converse shoes just like any hipster did. In years 2002 to 2003, hipster outfits are associated with men and women sporting tattoos.

In 2005, hipster outfits were completed with spectacular spectacles and boots. In 2007, hipster outfits got a retro throwback where men and women go for vintage stores with a huge collection of flannel shirts, retro floral dresses, and old denim jeans. In 2009, hipster outfits were transformed for where leather vests, skinny jeans, slip-on shoes, and plastic-framed glasses became popular. In the 2016 and so on, hipster outfits became trendier yet more minimalist—think of monochromatic outfits and streamlined designs.

Signs Hipster Outfits Are Just Perfect for You

Your beliefs and interests revolve around the hipster ideologies.

Do you know that hipsters have a deep interest in conserving the environment and turn to vegetarianism or veganism? In fact, women who love hipster outfits tend to be politically and socially liberal and think of global warming, conserving energy, and even recycling. Yes, hipsters are up-to-date regarding the social issues, art, and even food.

Remember, hipsters are the ones who reject the mainstream fashion. Instead of loving what’s the trend of the moment, hipsters tend to go for thrift and vintage shops, protesting against the materialistic society. Most of the time, a hipster closet consists of vintage clothes like graphic tops, skinny denim jeans, and retro accessories. Also, hipsters trend to eat organic and natural foods and some of them even support urban gardening.

You don’t want to look like everyone else.

Do you know that women who love hipster outfits have a deep appreciation for personal style and individuality? Nowadays, most women are influenced by fashion trends, style icons, and even film industry when it comes to dressing up. On the contrary, hipsters want to stand out and look different that is why they shop at vintage stores and thrift shops since shopping at the mall will increase the chance of looking like everyone else.

You tend to use body art like tattoos and piercing to express your individuality.

Do you know that body art like piercing and tattoos used to be unacceptable for the mainstream? That’s the reason why you should complement your style with hipster outfits. Some women even think of graphic tank top and vintage tees to showcase their tattoos. However, it’s better to go for more conservative outfits that will keep you professional at work, or go for more conservative hipster outfits if you plan to travel.

You want to maximize your wardrobe with versatile pieces.

Most of the time, hipsters know multiple ways to wear a basic item or even tie a scarf. Instead of investing in dresses, women go for basic staples like denim jeans, varsity jackets, tank tops, and cardigans to create hipster outfits. Instead of trendy shoes and sandals, hipsters go for effortless converse shoes and ankle boots that you can literally wear with everything. If you want to maximize your wardrobe without spending lots of money, it’s time to think of creating hipster outfits.

You love indie rock and alternative music.

If you know Harry Gibson, a pianist in the 1940s jazz, then you’ll have a better idea on hipster ideologies and even hipster outfits. In fact, his songs were all about drugs, adultery, and drinking, which were banned. Do you know that women in the 40s embraced hipster outfits just to show they are different and they reject the mainstream? If you love the theme of alternative music and indie rock songs, then you’ll likely find hipster outfits appealing.

You want a unique way to show off your individuality.

We all know that hipsters deeply influenced the fashion world, and if you want to stand out on your daily looks, go for hipster outfits. Do you know that hipster women go for the style because they want to be comfortable at the same time hip? If you want to channel your inner hippie, make your hipster outfits more personalized. Instead of going for certain fashion items that are known for hipster style, add some tweaks in your hipster outfits.

What You Should Know Before Wearing Hipster Outfits

We all know that hipster outfits got a bad rap in the past, and wearing the look can draw attention to you in a negative way. Remember, hipsters have certain ideologies that make them comfortable wearing hipster outfits because they make a statement that they want to show the world. However, if you wear hipster outfits and people look on you, you might be sending a different message that you don’t really want to.

Do you know that hipster outfits are known for their tricky to wear trends in real life? Depending on your fashion taste and personality, you can experiment on your hipster style before donning the actual hipster outfit of your choice. Also, keep in mind that most hipster outfits are not flattering for your body shape—think of low slung pants, shapeless dresses, and slouchy tops. The key is to select the right hipster items that will look great on you regardless of trends.

If you want to test the waters before committing to a certain hipster outfit, start with accessories. You may go for retro glasses and cool hat to complete your hippy statement. Or, start with a hipster-inspired print or pattern to channel the vibe effortlessly. Tie-dyes, nostalgic patterns, loud prints, and band graphics are great options too. As a rule of thumb, stick to hipster outfits that speak to your personality, make you more confident, and bring out the best in you.

Do you know that hipster fashion is changing the industry? Nowadays, there are fashion labels that are embracing the hipster style, making the look more of a high fashion and trendy. Most of the time, young women are the ones that embrace hipster outfits, and fashion brands are now making their designs cheaper yet of high quality to let them buy their items. More than that, there are lots of fashion trends that encourage wearing hipster outfits, making us to embrace the culture rooted from hippie lifestyle.

Apart from media, culture, and music, hipsters are now influencing fashion globally. Have you noticed that hipster outfits are not exclusive to hipsters nowadays, but actually became a fashion trend that can be worn by everyone? Even though the real hipsters were not embracing fast fashion and shop at vintage stores, you can now see a lot of hipster clothing on your favorite retail outlets. More than that, haute couture is now introducing hipster touches in their collection, making them look old, rugged, and slouchy.

Fashion Items You’ll Need to Create Hipster Outfits

Hipster outfits mean differently for everyone, but you can still go for key pieces that can channel the style and fashion you love. Most of the time, a flannel shirt or a vintage tee is enough. Do you know that flannel shirts became the transitioning piece during the fall of grunge fashion and the rise of hipster fashion? Flannel shirts might be known for a Western American style, but it also made the hipster fashion more stylish.

Also, hipster outfits are known for vintage tank tops, 70s band tees, and even 80s NBA championship t-shirt. A great thing, you can go for more modern graphic design that will channel your hipster attitude while still looking modern. If you love a sporty look, then varsity jackets and starter jackets are perfect to channel your hipster look. According to experts, hipster outfits and nostalgia strongly connected, so feel free to sport your retro and vintage pieces.

If you’re looking for a fashion piece that does it all, go for cardigans. In fact, cardigans are the perfect ensemble whether you wish for a casual or dressy hipster outfit. Or, opt for a casual blazer or a peacoat to make your hipster outfits more polished. In fact, your old blazers with patches and odd prints are perfect for creating your college professor chic look with a hipster twist. To complete your hipster outfit, go for suede ankle boots or even cowboy boots.

If you want a more modern way of creating hipster outfits, then think of distressed denim and sneakers. Depending on your personality, you may opt for denim pieces with exaggerated rips, along with high waist style bottoms. Instead of a vintage band tee or flannel shirt, think of relaxed tank tops and slouchy cardigans. You can also trade your converse shoes with fashion sneakers with metallic accents, leather trim, or even bold colored designs, making your hipster outfit trendier.

You may even create a smart-casual look on your hipster outfits. The key is to team your hipster outfits with sleeker pieces to dress up your looks a bit. Some women even keep their hipster outfits simple yet ladylike by incorporating feminine touches like floral prints, ruffles, and even lace ensembles. If you like, add some sexy vibe to your hipster outfits with spaghetti tops, crop tops, and sheer blouses. Or, make your hipster outfits more relaxed and off-duty with casual tees and track pants.

If you want to create hipster outfits without going too far from your style comfort zone, start with the pieces that you already have in your wardrobe. One of the best fashion items to create hipster outfits is your distressed denim jeans. Yes, the fashion staple is versatile and iconic, and it won’t be a big leap wearing them on the streets. This also includes denim jackets, denim vests, and even chambray shirts. If you have a limited budget on updating your wardrobe, simply visit your local thrift store.

To level up your hipster statement, trade your basic denim jeans with patterned pants and printed jeans. Think of floral prints, leopard prints, and even paisley patterns that will showcase your hipster-inspired style. Or, think of denim overalls that can give you a casual, effortless, or even sexy look depending on how you style them. Overalls are best worn with crop tops that will give you the statement-making hipster outfit.

If you want to showcase a mix of influences in your hipster outfits, think of Hawaiian prints and even other bohemian patterns. Just make sure you know the origin of those prints, so you won’t present a certain culture in a negative way. If you want to level up your hipster outfits, then incorporate some plaid patterns on your looks be it a shirt, a skirt, handbag, headband, shoes, or even pants. Most of the time, plaid scarves are the easiest way to channel the hippie look, not to mention they are practical enough.

To make things easier for you, go for accessories that will complete your hipster outfits. Most of the time, oversized blanket scarves are enough to create a hipster outfit, and they are versatile in the colder months too. When it comes to your shoes, you could never go wrong with Converse shoes and Doc Martens boots. They are just perfect for creating a hipster statement, and edgy enough to add some flair to your feminine style.

Even though hipster outfits get a bad rap, you can always make them more fashion-forward and chic. All you need is to be creative and fearless on your style choices. Indeed, hipster fashion is making a big comeback this 2019, so be inspired with our style guide for you to create cool hipster outfits on your next street look without trying too hard.

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