Vintage Flannel Shirts: 15 New Ways to Wear a Fall Favorite

• 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. 

woman wearing vintage flannel shirt and bucket hat
Credit: Hel Looks

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!

man wearing vintage flannel shirt and sweatpants in the woods
Credit: @lukenorthover4

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.

Credit: Audrey Kitching

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.

Credit: Sarah Spe

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. 

Credit: Hel Looks

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.

Credit: @xoninackim

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. 

Credit: Vu Thien

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!

Credit: Ivy Xu

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! 

man wearing a flannel shirt over overalls
Credit: Mannix Lo

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.

Credit: Dan Pantoja

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.

Credit: Julia

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. 

Credit: Tessa Diamondly

12. Add a bit of punk to a girly dress by throwing on a flannel and leather motorcycle jacket

Credit: JENNY MUSTARD .

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. 

Credit: Dorota D.

14. Layer a chunky fisherman sweater over a big flannel shirt so just a bit peeks out below the bottom hem. Pair with over-the-knee socks and big boots for a cute, cozy look.

woman wearing flannel shirt over band t-shirt and smiling
Credit: @jazminehannagan

15. Wanna keep it easy-peasy? Throw a vintage flannel shirt over a distressed band tee and skinny jeans for instant Cool Girl™ vibes.

woman wearing lightwash jeans, a flannel shirt, and a face mask
Credit: @anu_stha_

16. Or add it over a plain mock neck or turtleneck tee and light wash jeans for a weekend look with added warmth.

Credit: Maria C.

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!

Credit: Natasha Hide

18. For a model-off-duty look, throw on a vintage t-shirt, distressed jeans, and tie a flannel around your waist. It’ll define your waistline and provide extra warmth only when you need it!  

Credit: Filipa Lopes

19. Wear an oversized flannel over a skater skirt or pair of overall shorts to add another layer of visual interest. 

Credit: Agnija

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!

Credit: Martina McFarlane

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. 

Credit: Robyn The Bank

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.

Credit: Jamie Rose

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!

woman wearing tall boots and a large flannel shirt
Credit: @amrit_bilkhu

24. Throw a flannel shirt over neutral separates to add a twist to an otherwise simple outfit.