How to Dress Like a Hipster

Last Updated: July 5, 2021

Feeling out of place in your local coffee shop? Wondering if you dress like a hipster? Planning a trip to Portland in the near future? Or are you just looking for a little change in your day to day style? While being a hipster is much more complicated than simply dressing like one, this article will help get you on your way to becoming "totally deck."

Method 1

Method 1 of 3:

Being a Hipster Girl

1
Raid mom's closet for vintage tees. Ha, that's a funny way of saying "Go to any store that sells clothes for young adults." Never shop at "mainstream" stores (like Hollister, American Eagle, Aeropostale...) Have you not noticed the prevalence of pseudo-vintage tees everywhere? To be more, what's the word, authentic, shop at vintage stores, second-hand shops, or go around begging relatives.^{[1]
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Expert Source

Chloée Ohayon-Crosby
Fashion Stylist
Expert Interview. 24 July 2020.} (Goodwill, Urban Outfitters, Miracle Hill) Surely one of them has an old Reading Rainbow tee in a box somewhere from when they were 12.
- You want your tee to be either too small- chop off the bottom and make it a crop top, then throw it over that tank top/cami you hate- or too large,- tuck it into those high waisted pants you found at a garage sale- if at all possible. But if you found a gem of a Davy Jones tee from your favorite aunt that fits you just right, by all means. Davy's worth it.
2
Keep your neck warm and your hip-stardom intact with a scarf. The great news here is that scarves go with everything. EVERYTHING. Wearing a tank top? Scarf. Wearing a wedding dress? Scarf. Is it 95º out? Scarf.
- Familiarize yourself with at least a dozen ways to tie your scarf. If in doubt, just drape it nonchalantly around your neck, wrapped around once. You don't care what it looks like. You just love the comfy neck feeling, right? (Hipsters don't give a flip about anyone or anythings' opinion.)
3
Get flowery with dresses. Sometimes you like a healthy breeze down there, don't you? Dresses can be straight up more comfortable. But just like a good tee, your dresses should evoke a feeling from a different era. Flowery, vintage, and old-school is a safe bet. The flowery, the better.
- Did you find the perfect dress somewhere that's just a bit too big to be legal? Or maybe you found a dress that's too conservative and the sleeves need to be chopped off. This is the exact purpose neon bras and bandeaus were invented. Not kidding. Look it up.
- Too cold for a dress? Ha, good one! Have you not heard of wool tights? Wool, patterned, neon tights? If that doesn't solve all your problems, nothing will. Plain black tights under thick hiking socks is another great look, too.
4
Throw out all your boot cut or flared jeans. We know you have several pairs. You've been buying them since you were 10, apart from that one time around 2006 when skinnies made a brief appearance on the scene, only to slingshot to the other side of the spectrum with disco-esque flares. After that really confusing year, you just gravitated back to the safe boot cut. We all did. It's fine. But now you've gotta throw those out. It's skinnies all the way. Nothing else. Your ankles don't need to breathe!
- Have some jeans you like that don't make the cut (haha, puns)? Turn 'em into shorts. The higher-waisted and more mom-ish, the better. And when we say short, we mean short. Show off those gams of yours. Cuffs? Great. White wash? Great. Holes? Great. As long as it's denim, you're in the clear.
5
Pile on the accessories. Literally. Grab a pile and put them on. Play it like the claw game at the arcade (only you'll win every time). Did you end up with a wooden tribal bracelet, your grandma's ruby necklace, and a lace choker? Great. That works. It's all about haphazard combos.
- What may be outrageous to others is probably standard to you. A giant flower chilling on top of your head? Sure. A totally distracting enormous neon yellow hair clip? ...Why not?
6
Mix up your past looks. Since you were twelve, you've gone through (in order) a Hello Kitty phase, an N*SYNC phase, an emo phase, a prep phase, a flannel phase, a grunge phase, and now you're here. Wonderful -- now grab a piece from each look and combine them. Tada! Instant hipster. As easy as cheese in a can.
- Seriously. Hipster fashion is about a mismatch and clash of cultures all rendered meaningless if you really want to put a label on it. The main way hipster goes wrong is when people put thought into it -- so if you haphazardly go about your closet, bullet dodged.
7
Stick to anything but flip flops and heels. That's about the only rule for footwear. If it's not a flip flop and not a heel, you're golden. Loafers, cowboy boots, sneakers, it's all good. Flats are adequately hipster, too! Who knew something so harmless could be hipster-y?
- Make sure it doesn't look super new, too. If you just went out and bought a brand new pair of Chuck Taylors (you unique little snowflake, you), scuff 'em up. Those babies gotta be loved before they can set foot into Cafe Foucault.

Method 2

Method 2 of 3:

Being a Hipster Guy

1
Wear your sister's jeans. But no, seriously. If you can, do it. The skinnier the better. You want grip from groin to toe. And don't worry about "not pulling it off." That's part of the idea. In not pulling it off, you will be pulling it off. It's like opposite day back in sixth grade.
2
You want them to fit snug on your waist all the way down. In other words, tighty whities it is!
3
Get nostalgic. Anything that reminds you of when you were 5 should be part of your closet. Or anything that reminds your dad of when he was 5, too. If it's vintage, it meets the cut. The only, only logos in your closet should be ones of brands or industries that no longer exist. Excluding American Apparel, of course.
- It doesn't have to fit well. More on this later, but if it's too tight or too loose, cool. Size should be just about the last thing on your mind.
4
Fake bad vision. If you want everyone's hipster-dar (hipsdar?) to go off, wear thick, black-rimmed glasses.^{[2]
X
Expert Source

Chloée Ohayon-Crosby
Fashion Stylist
Expert Interview. 24 July 2020.} If you want everyone's hipsdar to reach decibels only dogs can hear, wear thick, black-rimmed glasses with the lenses popped out. Hey, you just like the added comfort of knowing your ears are still there. Nothing wrong with that.
- This style of glasses is reaching levels of overkill, so to be a bit more unique, opt for a different vintage-y style or a pair of outrageously colored Ray Bans. You can hardly go wrong with Ray Bans.
5
Be half business, half party. If you read the girl section above, you'll know that mismatching trends is part of the hipster look. In the same manner that you would mix up decades and styles, mix up levels of, for lack of a better word, swag. Under that Armani blazer of yours, throw on a TMNT tee (that makes the Armani okay somehow) with a knitted, plaid scarf, skinny jeans, and a pair of old, worn out penny loafers. Is he going to an interview? Is he going on a Pabst beer run on his bicycle right now? No one will know.
- Don't shy away from outrageously loud prints. Plaids, gingham, checkered, paisley -- anything that would make a girl reading Cosmo scream is a solid decision. You have a plaid tweed jacket and a striped cowboy shirt? Obviously those two go together.
6
Go for layers. If the weather allows it, layers are a good way to work in combinations, as discussed above. Cardigans can go on top of anything, for the record. Sweaters, long sleeves, it all gives more options to be ironic. A scarf on top of a tee under a trench coat? Sure, why not?
7
Think about your converse. Alright, folks, let's get real here: Everyone and their brother wears converse. It's not ironic, hipster, or making any statement anymore. All it says is, "Hey, I went to the Converse store and spent $40 on my shoes all while not caring about my image." So unless they're 15 years old and have molded to the shape of your foot, consider branching out into different realms of footwear.
- Doc Martens are a good place to start. Cowboy boots, old school Reeboks, Keds, and vintage-y loafers are decent, too. Just say no to flip flops.
8
Grab a messenger bag. Do a quick Google search for "Hipster messenger bags" and you'll be amazed. The freakin' things are CALLED hipster bags.^{[3]
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Research source} That's just society not being creative (as usual), but take it for what it's worth: To carry around your gear, you need a messenger bag.
- You might run into a few people that ask you about your "murse." That's a man-purse, by the way. That's fine. Let them. Your hands are free thanks to your bag to poke them in the eye. They deserve it for being so close-minded and ignorant.

Method 3

Method 3 of 3:

Getting Hipstery for Both Sexes

1
Avoid all things "mainstream." This means that big-name clothing brands like Hollister, Abercrombie, Aeropostale, etc. are off limits. This is important for two reasons: it emphasizes your individuality and shows that you are "anti big-business". To buy clothes, check out stores like Buffalo Exchange. If you don't want to buy second-hand items, look for a store that sells new clothes with a worn or vintage look. American Apparel, however, is acceptable due to the fact that it is sweatshop-free.
- Alright, so you live in a small-ish town where the only second-hand shop is Good Will? If you're caught in Urban Outfitters or H&M, you may not be proud, but you certainly won't be the only hipster in there.
2
Get a T-shirt that fits well. Note that "fits well" for hipsters is not the same as it is for non-hipsters. Mens' shirts should be somewhat tight-fitting with sleeves a hair shorter than a regular mens' shirt. Women's shirts, on the other hand, often mimic the "boyfriend" look. While women don't have to buy their clothes from the mens' section, consider investing in some shirts that are one or two sizes bigger than you'd normally wear.
- Sexy here is in not being sexy. Especially for women, conforming to the is-it-so-tight-I-can't-breathe look is not in the hipster repertoire (men's skinnies notwithstanding). Baggy and loose is just fine, if not preferred. It's about irony, not silhouette.
3
Leave no denim behind. Except for denim skirts, that is. Tight-fit jeans are a must for both boys and girls. Pants can be any color or pattern, including floral print or neon green. If pants aren't really your thing, consider some denim cutoffs. These can be any length for women, but all mens' shorts should hit just above the knee.
- Girls can also get away with the boyfriend look for jeans. If they're too long, cuff the hems once or twice.
- Denim jackets and shirts are also great additions to your hipster wardrobe. Don't be afraid to take a pair of scissors to them, either. Denim vests are just as cool as denim jackets (if not more so)!
4
Zip it up. It zips, right? It probably does. If you're hipster chic, you probably have a few hoodies hanging up in your closet right now. These go with everything. Literally, everything. The hoodie should be one of your best friends.
- Bonus points if you can pair it with a Fedora or a blazer or a printed, feminine dress.
5
Reuse old clothes. There's no point in going green for the environment and being vegetarian if you can't follow suit with your wardrobe. When in doubt, before you throw it out, see if you can "recycle" it. How could you turn it into something totally wearable?
- You don't have to keep them as is! A sweater could be turned into a pair of gloves (or a lampshade, book cover, pillowcase) for Pete's sake! You want original? Making it yourself is a pretty good way to start.
6
Prepare for the winter. While the intensity of your outerwear will depend on the season and where you live, it's important to be able to bundle up without losing your hipster look. Here are a few ideas:
- Pick up some flannel. Large, button up flannel shirts are a perfect addition to any hipster outfit, regardless of the color.^{[4]
  X
  Expert Source
  
  Chloée Ohayon-Crosby
  Fashion Stylist
  Expert Interview. 24 July 2020.} Ideally, these should not be matched with the rest of your outfit.
- Invest in a cardigan or two. These can be found anywhere, even the more mainstream stores such as Gap. Choose a button-up cardigan with a deep V and large buttons. If possible, buy it one or two sizes too big.
- Get an ironic crew neck sweatshirt or pullover sweater. Look for "grandma patterns" such as old flowers, kittens, or Christmas trees. Alternatively, look for a particularly "hideous" (read: awesome) pattern.
- Keep your head warm with a grungy grey beanie. This can also be swapped out for a neon orange color.
7
Utilize color. Because you're free to mismatch as much as you damn well please, you could be a veritable human Skittle if you liked. The more colors of the rainbow, the better. And if they're vivid or patterned, all the more reason to don them while taking photos with your analog camera at Brooklyn's Union Hall.
- Neon, neon, neon. Neon pants, neon shoes, neon accessories, neon Ray Bans -- just because you're not "in style" doesn't mean you won't be eye-catching! Normal colors go too well together (damn color wheel), so spruce up your closet with neons, patterns, and anything else that clashes.
8
Accessorize. Do not worry about matching here. Throw on anything you have; pair chunky and plastic with dainty and metal. Pendants of unexpected objects (such as owls or octopi), headbands with big bows on them, huge flower clips, chunky earrings, or anything that will draw attention. Anything with feathers is also a safe bet.
- Leather accessories are also big. Try leather satchels or backpacks, leather vests, and leather belts.^{[5]
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  Expert Source
  
  Chloée Ohayon-Crosby
  Fashion Stylist
  Expert Interview. 24 July 2020.}
- Invest in some cotton/linen scarves to throw over any outfit. Patterned is best. Keffiyeh scarves are definitely popular, although they are also somewhat controversial due to their religious implications. For something a little safer, try a small checkered pattern.
- Decorate your head. If it's too hot for a beanie, straw fedoras or fedoras with feathers are great hat options. Hats always put the icing on the hipster cake.
9
Get inspired by how other hipsters dress. Now that you know what makes a hipster on the outside, you'll be able to spot one from a mile away. In case you haven't noticed, they're everywhere (and some of them don't even know they're hipsters). If your local town doesn't have enough clues, here are some veritable cultural icons to turn to:
- thesatorialist.com, stockholmstreetstyle.feber.se, lookbook.nu, and cobrasnake.com are all good places to scout out your look. Hopefully you'll be first in line!
- Check out TV shows like "Girls," "Bored to Death," or "Portlandia" for inspiration. The fashion of your favorite musician works, too!
- Try to search Google images for "hipster clothes". This may give you good ideas of outfits to try.

Expert Q&A

Question

How should a hipster guy dress?

Chloée Ohayon-Crosby
Costume Designer & Wardrobe Specialist
Chloée Ohayon-Crosby is a Costume Designer and Wardrobe Specialist in Los Angeles, California. With over eight years of experience in fashion consulting, Chloée specializes in personal, film, theater, and commercial styling as well as image consulting and costume design. Chloée has worked as an assistant designer for the distinguished fashion house Chloée and as a freelance stylist with Glamour Italia. Chloée studied Fine/Studio Arts at the Ecole Nationale Supérieure des Beaux-Arts and Fashion Design and Merchandising at the world renowned ESMOD École Supérieure des Arts in Paris, France.

Chloée Ohayon-Crosby

Costume Designer & Wardrobe Specialist

Expert Answer

Look for a flannel shirt you can wear with some oversized full-frame glasses.
Question

How does a female hipster dress?

Chloée Ohayon-Crosby
Costume Designer & Wardrobe Specialist
Chloée Ohayon-Crosby is a Costume Designer and Wardrobe Specialist in Los Angeles, California. With over eight years of experience in fashion consulting, Chloée specializes in personal, film, theater, and commercial styling as well as image consulting and costume design. Chloée has worked as an assistant designer for the distinguished fashion house Chloée and as a freelance stylist with Glamour Italia. Chloée studied Fine/Studio Arts at the Ecole Nationale Supérieure des Beaux-Arts and Fashion Design and Merchandising at the world renowned ESMOD École Supérieure des Arts in Paris, France.

Chloée Ohayon-Crosby

Costume Designer & Wardrobe Specialist

Expert Answer

Look for vintage t-shirts with some old bands or brand names. Pair your shirt with a leather bag and a beanie to complete your look.