• Part of our How to Wear It series •
How to Wear a Vintage Sweatshirt
by Madeline Berger
March 25, 2019 | Last Updated: January 11, 2021
How to wear a vintage sweatshirt: a question that we've been asking ourselves since perfectly-aged sweatshirts took the internet by storm (again) and left us feasting our eyes on all the innovative ways people are wearing this '90s fashion favorite. This blog post was originally written in the spring of 2019, back when sweatshirts were a cool, cozy, slightly quirky top choice and not the quarantine uniform we all know so well by now. Sigh. Even with their new level of everyday popularity, vintage sweatshirts will forever give that effortless sense of casual cool (with a twist of '90s Nirvana-esque punk) that so many of us absolutely drool over.
Whether you've scored a vintage sweatshirt and looking for styling inspiration or you're currently curled up under a blanket reveling in the days you have a reason to put together fun outfits again, we’ve rounded up some of our favorite outfits from across the internet featuring vintage (and not-so-vintage) sweatshirts for your viewing pleasure. Ready to style your own? Check out our selection of over 300 recycled and vintage sweatshirts!
Style of the moment thanks to TikTok? Wear an oversized vintage sweatshirt with a tennis skirt for a cute twist on a sporty look, complete with a prairie-style headscarf.
Pair a classic crewneck sweatshirt with any type of embroidered logo with neutral chinos and a baseball cap for a very '90s dad look (in the best possible way).
Go a little bit Kim Possible, a little bit rock 'n' roll with a cropped-up vintage sweatshirt paired with oversized cargo pants and chunky sneakers.
Or keep your sweatshirt loose and flowing, matched with coordinating windbreaker pants. A bright '80s or '90s graphic gets a turbo charged vintage feel real quick!
Up the stakes on any hoodie and jeans combo by cuffing your pants with a dramatic single roll and swapping your usual sneakers for dress shoes.
If your vintage sweatshirt is on the fitted side, layer a flannel underneath and cuff the sleeves so details are visible throughout. It almost looks dressy, ay?
Speaking of dressy: pair a cropped vintage sweatshirt with wide-leg dress pants and sneakers for a polished look that still easily go from office to boardwalk.
Go full '90s by typing a windbreaker around your waist and throwing on a backward baseball cap. Extra points if you stick to pastels or jewel tones for super vintage vibes.
Pair a printed sweatshirt with a laced mini skirt and over-the-knee socks for a sweet look that isn't over-the-top girly. Dramatic earrings and simple shoes finish the look.
Nothing like sticking with a classic look: pair your vintage sweatshirt with slim-cut black jeans and sneakers for a tried-and-true outfit.
If it's not too bulky, tuck your vintage sweatshirt into a pair of jeans and throw on a thick belt to keep the outfit balanced. Throw on platform kicks for an extra punch.
Pair cropped tights or leggings under a denim mini skirt and pair with a cropped sweatshirt to add definite sporty touches to an otherwise overtly feminine skirt.
Leopard print can pretty much be considered a neutral at this point, and looks perfect paired with a vintage Harley Davidson sweatshirt—just add a beanie and hit the road!
Have a pair of statement sunglasses? Pair them with a coordinating graphic on an oversized sweatshirt and keep the rest of your outfit minimal and fitted.
Wear a vintage sweatshirt with a classic military jacket and denim shorts for a slightly rugged, slightly playful look that def more fun than your normal sweatshirt and jeans.
Tuck a hooded sweatshirt into a flowing maxi skirt and throw on a fanny pack for an unexpected outfit that can easily be dressed up or down.
Another classic favorite? Pair your vintage sweatshirt with distressed jeans and a baseball cap for the '90s dad or soccer mom look of your dreams.
Have an embroidered pair of jeans on hand? Wear them with a vintage graphic sweatshirt in a coordinating color for a punk-inspired look that's tons of fun.
Throw a leather motorcycle jacket over a vintage sweatshirt and mini skirt for a cool girl look that's bound to be handy for tons of occasions.
Pair a solid-colored vintage sweatshirt with fun biker shorts to keep you cozy up top and direct the eye to the star of your outfit. Add a fanny pack to define the waist!
Wear a vintage sweatshirt with the now-again popular yoga pant trend or something more spicy like these velvet bell bottoms for an unexpected silhouette.
Throw a blazer over a hooded sweatshirt and add a baseball cap for a look that checks both the boxes of 'officewear cool' and 'cozy as heck'.
Feeling crazy? Layer a vintage sweatshirt under a button-up dress or jumpsuit! Tie a sash or add a belt to define your waist and leave the top buttons unbuttoned.
A vintage sweatshirt is a perfect companion to a metallic pleated skirt—it totally tones down a skirt with an otherwise hard-to-avoid party feel. Add sneakers to finish!
Have a truly oversized vintage sweatshirt or hoodie? Simply wear it as a dress. Add over-the-knee boots and a coordinating bag for an A+ going out look.
Layer a classic white button-up or buttoned tunic under a vintage sweatshirt and top with a camel coat for a great look that's ready to go anywhere and do anything.
Wear a vintage sweatshirt or hoodie with matching (or similarity toned) pants for a monochromatic outfit that looks automatically elevated. The more volume, the better.
Ready to shop for your own vintage sweatshirt? We've got styles featuring everything from coveted brands like Nike and Adidas to the coolest '90s era graphics. Our small team hand-selects every item in our vintage shop and new items are added weekly. Click below!