20 Hipster Style Men Outfits: How to Dress as Hipster?

The hipster style knows NO rules and celebrates individuality, creativity, and free spirit. Hipster-style men are trending like no other. So, if you want to elevate your style according to it, little small changes are enough. So, here is a complete guide to 20 hipster-style men Outfits and How to Dress as Hipster?

Let’s have a look!

What is a Hipster Style?

The history of hipsters dates back to the beginning of the 19th century, when a long-forgotten word burst into the fashion world: Hipster. By the middle of the last century, this trend originated in America in the 1940s and was quite well known.

It has notes of Bohemian culture and looks punk and very stylish. You may have everything in your wardrobe you need to pull hipster style as it’s all about the right pairings and attitude. Mens hipster style has evolved and become mainstream and very attractive. So, keep reading for every detail about this style to rock the hipster look.

Different Types of Hipsters 

Hipsters have a particular sense and have different types. There are many popular celebrities who are hipsters and celebrate their unique kind. So, here are different hipster style men which are quite popular:


As the name says, natural hipsters, let the style come to them organically. The natural men hipster style has a balance of clothes with casual and some iconic accessories like trending men’s necklaces. Some classic celebs with natural hipster looks are Joaquin Phoenix, Gwyneth Paltrow, Parker Posey, Johnny Depp, and Morgan Freeman.


Newbies are the coolest hipsters who are common in college. They are young, free, and have eyes full of dreams. They can rock any hipster look. To style them, get tattoos, a skating board, loose t-shirts, baggy trousers, and lots of dashing bracelets on your wrist.


Academic hipsters are smart, intelligent, and have immense knowledge of certain subjects. They have semi-formal style, classy glasses, stylish watches, and accessories. They’re less distracted and very much focused. Some examples are Wes Anderson, Philip Seymour Hoffman, and Rivers Cuomo.

DIY Hipsters

DIY hipsters are bold and attractive. They start doing anything they love and begin it from scratch. It can be music, dance, or any form of art. The characteristics are free nature, bold makeup, bright clothes, and lots of zest for life.


Vintage hipsters are period people who follow the trends of the 50s and 60s. The checks, apparel, and style resonate with retro fashion, giving an impression of a thoughtful, deep, and charming personality.


Health-ster is trending and becoming very popular. These hipsters focus on yoga, meditation, exercise, and a good diet and prefer rich living. In addition, their thoughts are unfiltered, and they have a unique fashion sense. 

Hick -ster

Hick-ster is the epitome of being a hipster. They have multiple tattoos, use bold language, have many accessories, and are kind at heart. They love art, expression, and freedom in all forms. They are more like bohemian hipster-style men and stand out in a crowd.

20 Hipster Style Men Essentials you should Have

  • A T-shirt With a Print

Hipster-style clothing for men has prints that can be either image of fairy tales and cartoon characters, fantastic animals, schematic animal outlines or light inscriptions, or a picture of London.

  • The “granny” Jumper

A long or short jumper in a large knit (ideally – stretched) is a must-have in the hipster man’s wardrobe. You can also replace them with a vintage-inspired knit or printed jumper. Hipsters respect homemade pieces. Hand-knit clothes are ideal.

  • Trendy Necklaces

The urban hipster style men call for layering the neck with trendy necklaces. Single, multiple, or chains with pendants look super cool. They go with all casual and formal wear. So, elevate your outfit with these minimalistic to bold necklaces to achieve a hipster look. 

  • A Plaid Shirt

A plaid shirt has a criss-cross of color threads to form delicate checks. These look best in flannel fabric and are available in all slim, regular, and loose fits. It looks great and has lots of character.

  • A Long Cardigan

Hipster winter style men and long cardigans are a great combination. They can be monochrome, have checks, print, and designs. They go well with jeans and shirts. The relaxed fit portrays a free mind and attitude.

  • Skinny Jeans

Skinny jeans are especially great for novices and hick-sters. It goes with loose upper wear and looks very stylish. Pair it with nice boots, and you’re good to go.

  • Viking Accessories

Nordic mythology and Viking accessories not only complement vintage hipsters but everyone. They have lots of personality and area available in dashing Viking bracelets, necklaces, rings, etc.; the symbol of Thor’s hammer, etc., looks very charming.

  • Cool Watch

A watch can never go wrong and especially complements the hipster persona. It became popular in hipster style men 2015 and is making a huge comeback. Casual, formal, or funky watches complete a unique hipster personality.

  • Statement Earrings

Visualize loose t-shirts, rugged denim, Chelsea boots, and cool statement earrings. Well, it looks so clean, stylish, and appropriate. Small to large earnings go with various outfits and look very expressive.

  • Ankle Shoes

Ankle shoes like deserts, Chelsea, sneakers, and other boots have a great hipster look. They work with both funky and formal dressing. They are with or without lace options and look great with every outfit.

  • Leather Jacket

Leather jackets are essential and are an evergreen statement. You can wear any color and pair it with t-shirts, shirts, and sweaters. The sleek look and shine look amazing and are a must-have in hipsters’ wardrobes.

  • Denim Jackets

Loose denim jackets over t-shirts, shirts and loose jeans look adventurous and cool. Denim shirts can go with various outfits and represent hipsters’ vibes perfectly.

  • Oversized Trousers

Loose, comfortable, and stylish trousers are a must for any hipster. You can go for chinos and cargo, which are breezy and chic. They are best to go to bottom wear which lets you be yourself.

  • Scarves

Summers or winter scarves suit hipster clothing style men and look eye-catching. You can pair them with t-shirts, shirts for men with jackets. Scarves symbolize creativity, art and look very stylish.

  • Checked Wear

Checks are evergreen in hipster style clothing men, and always look smart. Checks in shirts, jackets and even trousers look very stylish. You can go for long checked jackets and checked scarves. Try something monochrome and pair it with loose check trousers.

  • Bold Rings

Rings have been a bold statement for ages. Hispertser love to layer their fingers with simple to bold rings. An artistic skull ring with a basic outfit will look incredible and dominant.

  • Cool Shorts

Shorts which are available in both casual and formal styles look very attractive. It perfectly suits hipster summer-style men and goes well with shirts, blazers, and even t-shirts.

  • Floral Wear

Summer, beach, and tropical floral wear resonates well with the hipster look. It’s for some who are hick -ster and know no rules. This hipster style for men in the form of shirts and t-shirts looks very bright and radiant.

  • Cool Eyewear

Cool glasses, sunglasses, etc., seem interesting and add personality to your outfit. You can try large frames or cool sunglasses. If you are a natural hipster and unframed sleek glass will look great too.

  • Stylish Caps

Head accessories and whispers have a long reaction. You can style your hair with caps, hats, beanies, and more. They give a street hipster vibe and portray the carefree soul perfectly.

FAQ on Hipster Style Men

The key difference between hippies and hipsters is that hippies care less about social norms; they’re content with their limited living and don’t bother anyone. On the other hand, hipsters show social responsibilities, have a social life, and love to follow trends. They are artistic, vocal, and very confident. They are modern and love technology—photography, styling, and yet living a free life.

Right attitude and accessories are very important for a hipster personality. Hipsters love wearing ankle shoes, slip-on footwear, a loafer, and anything that’s easy, bold, and trendy.

Hipster accessories are stylish as they celebrate art, history, and fashion. Some of the best ones are Viking, stone, beads, Celtic, leather necklaces, rings, and bracelets. Cool watches also make amazing hipster accessories and look very cool.

Hipster hairstyles for men are less varied than those for women. The hair is usually cut shorter at the temples, longer at the back of the head, and the fringes are longer. The hair can be styled in a “tuft” or disheveled on the top of the head. Another hairstyle option for men is to comb the hair with fringes to the side, and have a beard and a mustache, although these are not necessary attributes of the hipster style.

Yes, bohemian hipster style is a mix of boho and hipster style. It looks quite attractive and appreciates art and a free mind. People with this style prefer colorful, loose, and trendy accessories. It can be cool jewelry, stylish watches, hats, etc.

True hipsters are the connoisseurs of all fashion trends. They are social networkers, travelers, gadget lovers, sad philosophers, and creative professionals. 

They love to party and can party their hearts out, constantly taking pictures and posting them on the internet. They allow you to consider them bohemians, as they are only interested in what they love. They may or may not work if circumstances do not allow it—London’s main metropolis of hipsterism today.

The new term for hipsters is “Yuccies,” which means young, urban, and creative. They have top-notch fashion, which can be subtle or bold. In addition, they practice creativity through art and knowledge. They are social and very kind at heart.

Hipster-style men’s Tumblr era is coming back to when teenagers used Tumblr for vlogging etc. Now, with other digital social networking platforms, gen Z call hipsters “indie sleaze” or sometimes “yuccie.” These are new lingos and may turn to a new kind of hipster style.


This was a complete guide to hipster-style men and how you can achieve the look. The thumb rule is to appreciate your persona and be real, creative, and active. So, style your outfits with the right accessories and practice hipster values for a beautiful life.

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