• Part of our How to Wear It series •
Answered: How to Wear Vintage Flannel Shirts
by Madeline Berger
November 4, 2019 | Last Updated: January 19, 2021
Hello, everyone, and welcome to the midst of Flannel Season (although let’s be real—Flannel Season is Every! Season!). If you’re anything like us, you can always do with another way to wear the timeless vintage flannel shirt.
For the last few (read: many) months, you’ve probably been wearing a more plentiful assortment of sweatshirts, sweaters, and straight-up pajamas. If you’re looking to mix it up a little, flannel shirts offer a similarly casual feel but with a floaty, grunge vibe that our sacred sweats just don’t quite capture. Check out
fifteen twenty-two different ways to style our favorite button-up and shop our vintage flannel shirts and new women’s flannel shirts while you’re at it.
1. Mix textures and keep it ’90s-inspired by adding an oversized flannel to a crop top, denim shorts and tights. Throw on a bucket hat and statement earrings to finish!
2. Have a big, heavyweight flannel shirt? Wear it over your sweats for a look that can take you through the woods and into your local coffee shop just as easily.
3. Channel your best ’90s grunge by pairing a floral print with your flannel and adding a vintage band tee. Don’t forget the Kurt Cobain-esque sunglasses.
4. Add a flirty touch to your flannel by pulling the shirt off your shoulders, tucking it in, and adding a classic belt and heel to tie the outfit together.
5. Feeling spunky? Throw an oversized plaid scarf over your flannel shirt for a plaid-on-plaid look that’s bound to turn heads. Add stripes for even more oomph.
6. A flannel shirt makes a cute addition to an all-black outfit of a crop top and joggers. Combat boots add a slight Lara Croft vibe that we’re here for.
7. Button your flannel up to the collar and tuck it into a major trend of the season: a midi/maxi length pleated skirt. Top it off with matching accessories!
8. Add a flannel shirt as a mid-layer between a plain tee and your favorite winter jacket. The pop of pattern will make the boring days of winter outerwear just a little more interesting!
9. Throw a vintage flannel on top of oversized overalls. It’s a great way to enhance the playful nature of the outfit and break up the one-piece vibes that are inherent to the ‘fit.
10. Keep it classy by fully buttoning your flannel shirt and pairing it with straight black pants. Clean Chuck Taylors and a rolled beanie keep the look casual yet put-together.
11. Wear your inner-wear as outerwear! Throw your favorite bralette over a big vintage flannel and unbutton below the bralette hem for a bit of extra flow. Add statement pants and call it a Saturday night look.
13. Winterize a summer look by wearing an oversized flannel with a crop top, high-waisted shorts, and fun tights for just a bit of warmth.
15. Wanna keep it easy-peasy? Throw a vintage flannel shirt over a distressed band tee and skinny jeans for instant Cool Girl™ vibes.
16. Or add it over a plain mock neck or turtleneck tee and light wash jeans for a weekend look with added warmth.
17. Wear a flannel shirt in one of the most classic ways possible—with jeans, a winter jacket, and giant accessories to keep you protected from the frigid weather. We love how Maria kept to muted tones outside of the bright flannel!
19. Wear an oversized flannel over a skater skirt or pair of overall shorts to add another layer of visual interest.
20. Loosely tuck a flannel shirt into a pair of shorts if you’re lucky enough to live somewhere where winter doesn’t actually mean freezing your rear off. Add a cute fedora and your favorite bag!
21. Play with colors and texture by using your flannel shirt as a base layer underneath an ultra-distressed sweater and colorful leather jacket. Pair with a mini skirt to play with proportion and don’t step in too many puddles.
22. Wear your flannel shirt with a crop top and distressed denim shorts if you’re staying indoors for the night! To up the casual factor, throw on a slouchy beanie.
23. Tuck your flannel into a structured skirt and layer on a necklace for a flouncy take on the lumberjack staple. Add tall socks or tights to keep warm!
24. Throw a flannel shirt over neutral separates to add a twist to an otherwise simple outfit.
Vintage Greatland Sportswear Thick Flannel Shirt 3639$29.99
Vintage Flannel Shirt 3638$19.99
Vintage Flannel Shirt 3637$24.99
Vintage Premier International Flannel Shirt 3636$19.99
Vintage Britches Great Outdoors Flannel Shirt 3635$24.99
Vintage Flannel Shirt 3634$19.99
Vintage George Flannel Shirt 3633$19.99
Vintage Flannel Shirt 3632$19.99
Vintage Flannel Shirt 3631$17.99
Vintage Flannel Shirt 3630$14.99
Vintage Flannel Shirt 3629$19.99
Vintage Flannel Shirt 3628$19.99