17 Cute Flannel Outfits to Shop in 2020 — How to Wear Flannel

street style september 20   milan fashion week springsummer 2020

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To be specific, flannel is a type of soft woven fabric, but it’s kind of become a catch-all term for plaid button-up and button-down shirts in general, even ones made of cotton, wool, or other materials. More than shirts though, there are flannel jackets, skirts, and, yes, pajamas and robes. Every year when it gets cooler outside, it becomes popular again just because something about it is so cozy, comfy, and just so… fall? There are also tons of color combinations you can wear with the plaid patterns, so it’s basically one of the most versatile pieces in your autumn wardrobe, if you don’t already own at least, like, five flannel shirts already.

Keep scrolling for 17 cute flannel outfit ideas, so you can see how to wear it yourself whenever the season of PSLs and falling leaves rolls around. Speaking of the imminent transitioning seasons, feel free to click here for other shopping ideas including the best jean jackets, cute fall outfits, the best fall boots, and all the fall 2020 trends for fashion, bags, shoes, and jewelry.

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this cozy dress with clogs

Bianca Grey Midnight Sky



A roomy button-up flannel dress with gray socks, clogs, and a beanie just screams fall. You can also opt to roll the sleeves up on the dress if you’re feeling a lil too toasty. 


this mixed pattern sitch

Plaid Pattern Jacket



A mismatched flannel jacket goes perfectly with red check drawstring pants. Don’t ask me how! If you’re all about playing with patterns, this is definitely the outfit inspo for you. 


this shirt and short combo

Getting Rad Plaid



Sometimes the day just calls for a flannel and simple denim shorts, especially if there are transitional temperatures involved. Throw on some combat boots with this and you’re all set. 


this effortless look

Oversized Shirt Dress in Brushed Check

Missguided Plus


A blue-and-gray dress looks so good with neutral accessories; plus, you can always undo some buttons and show off a cute bralette underneath. 


this glossy number

Coated Flannel Dress



Ever heard of coated flannel? Yeah, me either. But if you want something different go with this shiny, balloon-sleeve mini in a fall-worthy plaid. Equally shiny lace-up shoes add the finishing touch. 


this button-up and black jean duo

Flannel Shirt-Jacket in Tartan Plaid



A red-and-white flannel loosely tucked into boyfriend jeans with ballet flats is the only outfit I wanna wear come fall. 


this fun suspender skirt

Burgundy Purple Plaid Challis Button Front Suspender Skirt

Put a unique spin on a flannel ensemble and go for a suspender skirt instead! The style is made for layering with T-shirts, long sleeves, sweaters, you name it. Dress it up with heeled boots or down with lace-up flats. 


this elevated mock neck with jeans

The Lightweight Flannel Mockneck Shirt



No buttons here! A flannel in this silhouette looks super chic and profesh, even more so when paired with kitten heels and a sleek top handle bag. 


this outdoorsy vibe

Knit Belmar Shirt



The red-and-black buffalo check pattern is always a fall staple. Layer it with a turtleneck and add jeans and a beanie, and you’ll look ready to jump into a pile of crunchy leaves. 


this drop-hem dress with booties

Shirt Dress in Check Print

Only Curve


If a plain ol’ shirt dress is, well, too plain for you, consider one with a drop hem that adds a tiny extra ruffle. Throw on a black felt hat and patent leather boots with a red and burgundy one for the ultimate autumn vibes. 


this vintage aesthetic

Vintage ’60s Plaid Shirt



A cool styling trick is to leave the bottom buttons open and close the rest (even the tiny ones on the collar!). You can pile on statement necklaces for some shine, and baggy jeans give it a retro feel. 


this thick jacket and turtleneck

Oversized Checked Felt Jacket



A flannel also works great as a jacket, especially when the material is thicker and the length is longer. Wear it with a sweater underneath and add some leather touches (pants, boots, bag, etc.) to make it more elevated. 


this skirt and zip-up sweater

Check Pleat Midi Wrap Skirt



Okay, I’m actually obsessed with this outfit. The half-zip sweater, plaid skirt, snakeskin print bag, and patent leather boots mixes up so many textures and prints in the best way possible.  


this half-tucked shirt with belted pants

Keeper Button-Down in Flannel Plaid

Alex Mill


Belted pants and loafers look less stuffy with a loose-fitting flannel tucked into them. This navy and green color combo is subtle while still adding some overall color.  


this cozy robe

Ultra Soft Flannel Robe



Hear me out: Your loungewear counts as an outfit! If you’re not planning on leaving your house, but you still want to look cute, go with a flannel robe that you can wear fun slippers with. 


this short-sleeve option with cutoffs

Boxy Shirt in Check Print

Noisy May


Still hot outside in September? Get yourself a short-sleeve one and wear it with edgy cutoffs and boots. 


this luxe flannel with two-toned jeans

Oversized Red Flannel

Romeo Hunte


Wow, is this one pricey, but also flannels and the buffalo check pattern is kind of designer Romeo Hunte’s thing. This is one of those pieces that lasts forever, and it’s the right fit and style to wear as both a shirt and jacket. Throw it on with casual jeans or wear it with a midi skirt to dress it up. 

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