How to Wear Vintage Pants

• Part of our How to Wear It series •

How to Wear Vintage Pants

by Madeline Berger
July 16, 2020

I don’t know about you, but finding a really good pair of vintage pants produces a feeling for me similar to that of snagging the second-to-last office donut or being the first one to spot a rainbow after an unexpected storm. In short, a good pair of vintage pants is absolutely delicious. And whether you’re looking for high-waisted, pleated cigarette pants straight out of the 1950s or the more grunge-inspired look of ’80s and ’90s vintage plaid pants, you’ve come to the right place. We’ve rounded up fifteen of our favorite looks from stylists around the world on for your viewing pleasure, along with a few favorite pairs from the nearly two hundred vintage pants we currently have in stock!

Credit: Weronika Bukowczan

1. A pair of vintage plaid pants look perfect paired with extra chunky sneakers. Balance it out with a cropped cardigan and coordinating jewelry!

Credit: Uwila Simposya

2. Love Uwila’s cuffed look with white tube socks and vans. Their flat-brimmed hat and delicate jewelry keep the outfit from looking too obtusely grunge. 

Credit: Dominic Grizzelle

3. Wear cropped vintage pants a bit slouched when paired with a hoodie. Dominic adds bright shoes and futuristic glasses to give the look a modern edge. 

Credit: Iwona

4. Vintage pants look super sophisticated when paired with a chunky sweater and belted at the waist. Iwona added cowboy boots to put a twist on the outfit! 

Credit: Jared Acquaro

5. Pairing khakis and a button-up shirt is a classic move most of us can get behind. Throw on a denim trucker jacket and fedora to spice it up! 

Credit: Olga Dupakova

6. Have a pair of oversized dress pants? Belt a poncho around your waist to automatically create a dramatic silhouette and also stay comfy as heck. 

Credit: Jacky

8. Automatically up your cute factor by wearing a pair of high-waisted vintage pants with a crop top and oversized button-up shirt (don’t forget the sneaks!).

Credit: Iwona

9. Look instantly polished in an easy monotone look: match your vintage pants to your jacket! Bonus points if they’re in a fun color like Iwona’s lime green. 

Credit: Dominic Grizzelle

10. Make it all about texture and pattern. Wear your pants with an interesting jacket and varying under-layers to add lots of dimension while staying practical. 

Credit: Jessie Barber

11. Wear your vintage corduroy pants with a coordinating striped tee to keep things super playful. Add matching sunglasses for even more fun!

Credit: Miamiyu K

12. Keep the focus on an extra cool pair of vintage pants by keeping the focus where it should be. Throw on a black turtleneck and call it a day!

Credit: Iwona

13. Menswear, schmenswear. Tuck a pair of vintage pants into your hottest socks and sandals getup and pair with a belted oversized blazer. 

Credit: ★masaki★

14. Wear your vintage plaid pants with a graphic tee and denim vest to achieve the punk/skate vibes of your wildest dreams. 

Credit: Anna Borisovna

15. Pick up a pair of cargo-inspired vintage pants and pair it with a tonally-similar top. Match your sandals to your belt and call it a khaki dream. 

Ready to shop for your own pair of amazing vintage pants? We’ve got styles featuring everything from snappy plaid to high-waisted slacks. Our small team hand-selects every item in our vintage shop and new items are added weekly.