How to Own a Vintage T-Shirt

How to Own a Vintage T-Shirt

by Madeline Berger
July 19, 2018

The vintage t-shirt was many of our first forays into the world of used clothing for good reason. They’re full of stories, personality, and fun; they can look great cropped or super oversized. They look intentional in any condition, whether full of holes and stains or deadstock. Because of this, there are a million ways to wear whatever vintage t-shirts are in your closet. That’s a lot of options, though, so we’ve rounded up seven of our own for your viewing pleasure and resulting Pinterest boards.

Paired with ultra-’80s Suspender Pants

There are few things more classic than an I Heart NY vintage t-shirt, seen on tourists and Times Square sidewalk shops from times past. While it may feel a little too cliché for a normal pair of jeans and sneakers, just pair it with a pair of throwback, high-waisted, acid-washed suspender jeans with coordinating straps and sunglasses for a look that might turn even the most seasoned New Yorker’s head. Can’t find a pair as crazy as this? Bust out your dad’s suspenders and call it a day.

Layered Under a Classic Flannel

While some may roll their eyes at the boring nature of this combo, I beg to differ. There is nothing—I repeat, nothing—more classic (at least for a midwesterner such as myself) than a vintage t-shirt underneath a worn-in flannel shirt. Top it off with a beanie in a popping color and wave hello to October in Minnesota.

Super Oversized and Cinched with a Silk Shirt

Remember the kids in middle school who wore the shirts featuring an array of dragons, flames, and barbed wire most days of the week? Maybe you were that kid. Heck, maybe you still are that kid. Whatever your look, respect. This oversized Dragon’s Sword Vintage T-Shirt looks sick worn as a shirt dress, with a vintage silk shirt tied around the waist to add definition and additional texture.

Tucked into Vintage Levi’s with a Shoestring Belt

Outside of a perfectly-fitting vintage t-shirt, a perfectly-fitting pair of vintage jeans is one of history’s greatest gifts. The jeans pictured are Levi’s Student Fit from our vintage denim jeans section, which are cut closer to to the hips and often come in smaller sizes than Levi’s classic 501s. The vintage t-shirt pictured is great because it displays how vintage it is right on the front (1987—ancient history!). Cleanly tucked in and with a skateboarder-inspired belt made out of a shoestring and cherry-on-top lowcut Vans, this all-vintage outfit still manages to feel fresh as hell.

Base Layer for a Flannel and Denim Jacket

This vintage t-shirt only peeks out beneath the warmer layers on top, but you still get the grungy, band tee effect. Feeling crazy? Find layers that have zippers instead of their classic buttons.

Paired with your Favorite Corduroys

Are you the type of person that shakes things up? If you’re nodding your head or currently shaking something, pair your vintage t-shirt with a pair of vintage corduroy pants (we like that they’re roomier than most contemporary versions) and break up the marriage that is vintage tees and jeans forever.

With an Oversized Leather Jacket and Vintage Jeans

Are you a city slicker or packing up for Sturgis? Both? Neither? You probably have a leather motorcycle jacket somewhere. The bigger the better, in this case. We’ve thrown one right over an oversized vintage t-shirt loosely tucked into oversized jeans, with the fashion faux-nah that is mixed brown and black leather. There is something undeniably fashionable about breaking rules, such as only wearing oversized on one part of your body (can’t mess with proportions too much) or sticking to one shade of leather. This outfit breaks both, and we love it.

How do you wear your vintage t-shirts? Tag us on Instagram with your looks—we’d love to see!