JOIN THE 'FRIENDS WITH BENEFITS' COMMUNITY →

  • Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
Style Girlfriend

Style Girlfriend

Helping guys look, feel, and act their best

Search
  • Women
  • Style
  • Grooming
  • Shopping
  • About
    • Meet Megan
    • Community
    • Contact
  • Friends With Benefits
  • Search
Style 5 Days 5 Ways

How to Wear a Flannel Shirt Five Ways

Embrace fall's favorite fabric
flannel shirt outfit ideas

by Gabi Meyers Updated: March 26, 2024

Products are curated by Style Girlfriend editors. Purchases through our links may earn us an affiliate commission.

Guys, fall is officially here. While it’s time to tuck away your shorts into the back of your closet, it also means it’s time to pull out one of my personal favorites…flannel. And we’re going to show you how to wear a flannel shirt five ways today, so let’s get to it.

The difference between flannel and plaid shirts

ryan gosling wearing plaid flannel shirt

Sort of like how an apple is a fruit, but a fruit’s not always an apple…flannel shirts are often plaid, but plaid shirts aren’t always made of flannel.

Plaid is a pattern, while flannel is a fabric. That means when we talk about a plaid shirt, we’re not necessarily referencing the cozy, fuzzy kind of shirt. You can head here to check out ideas on how to wear plaid shirts not made of flannel in a stylish way.

Are flannel shirts stylish?

Yes! Flannel shirts are super-stylish! Why? Because a) plaid is one of the greatest pattern of all time, and b) flannel is one of the softest fabrics ever. The kind that only gets better with age.

Bottom line? A flannel shirt is the casual, cozy subtle statement-making shirt that will be your weekend workhorse for fall.

MONDAY
casual office, flannel, plaid, layer, fall, saturdays, warby parker, grenson, obey, fossil

How to wear a flannel shirt to work:

SG Says: Wear your flannel to work under a sweatshirt with cropped trousers and brogues.

This is the fall season’s heavyweight (wardrobe) champion. Once reserved for utility more than style, the flannel shirt has been updated with slimmer cuts, unexpected light colors, and patterns like gingham and stripes to add unique perspective to a rugged favorite. Recutting this 90’s grunge mainstay has made way for a seamless transition into a dressed up version by shortening the length, narrowing the torso, and even spreading the collars.

TUESDAY
plaid, flannel, casual, skate, huf, vans, acne studios, bonobos, united by blue

How to wear a flannel shirt out with friends:

SG Says:  Rock your flannel as a jacket over a comfy tee and jeans, for those committed to the casual side of flannel.

WEDNESDAY
united by blue, spitfire, chinos, j.crew, denim jacket, bass

How to wear a flannel shirt on date night:

Wear it well: Roll up your pant legs to show off your boots.

THURSDAY
plaid, flannel, cozy, cashmere

How to wear a flannel shirt to a casual office:

Wear it well: Achieve a cozy-yet-professional outfit by combining all the softest fabrics of fall – cashmere, flannel, corduroy, and suede.

FRIDAY
flannelfriday2

How to wear a flannel shirt on Friday night:

SG Says: Mix bad-boy elements like a leather jacket and flannel with goody two shoes loafers for an elegant air of intrigue.
 
***

A few more tips on how to wear flannel

  • A flannel shirt is versatile if you’re willing to take risks. Wear it buttoned all the way up for a modern, urban look, or open over a crewneck tee.
  • For a more rugged look, pair a flannel shirt with a field jacket and leather boots. Better yet? Double layer it with a denim jacket under your field coat.
  • Going business casual with this look? Think no suits, no jeans. The middle ground between the two is where you’ll want to land – sturdy chinos are a great place to start. While some company dress codes favor slacks without a blazer and other consider denim with a sport coat “business casual,” it’s best to start in the safe-zone by asking a co-worker or two.
  • You can mix color, pattern, and texture – especially with a flannel shirt that can often times be a stand alone piece. Pump up your look by layering on a canary yellow sweater and roll up your sleeves to match the edgy vibe. If the early fall days are still too warm for an extra layer, take a page out of the 90’s playbook and tie your sweater around your waist for an intentionally laid-back, yet comfortable ensemble.

Want to see more ways to wear your favorite pieces? Check out outfit ideas for field jackets, black jeans, and denim jackets.

Gabi Meyers

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.

More articles by Gabi Meyers

Twitter Instagram

Primary Sidebar

The Latest

couple holding hands and walking

10 Fun and Affordable Summer Date Ideas to Try This Weekend

stylish man wearing a butter yellow knit polo shirt walking away from a white jeep

This Summer Color Looks Smooth Like Butter

men's summer vacation packing roundup

Men’s Summer Vacation Outfits: The Ultimate Packing List

5 Cool Men’s Brands to Know Right Now

Trending Now

  • close-up of a man wearing white nike tennis shortsThe ’90s Nike Tennis Logo is Back
  • summer business casual outfit ideas for menGo Sweat-Free in these Men’s Summer Business Casual Outfits
  • 5 Cool Men’s Brands to Know Right Now
  • stylish man wearing a butter yellow knit polo shirt walking away from a white jeepThis Summer Color Looks Smooth Like Butter
  • side by side images of men dressed in classically elegant "Italian summer" styleThe Guy’s Guide to Effortless Italian Summer Vacation Style
  • cool baby gearIYKYK: The Best Baby Registry Items Dads Need to Know (That Moms Already Do)
Style Girlfriend
  • Instagram
  • TikTok
  • Twitter / X
  • Pinterest
  • RSS Feed

Connect

  • newsletter
  • careers
  • contact
  • advertise

More From SG

  • Friends With Benefits
  • shop our picks
  • read the blog
  • about us

Style Girlfriend may earn commission from products that are purchased through our site.

© 2025 · Style Girlfriend · Terms · Privacy · Accessibility