Plaid Comes Back Every Fall, But These 5 Outfits Make It Look Thoroughly Fresh
You know those memes about the fall girl in her riding boots and cable knit sweater clutching a pumpkin spiced latté? That's me. I love fall and I love fall fashion, including all the classics like brown, burgundy and—of course—plaid. These cheeky checked pieces come back every fall and winter, and they're continually beloved for a reason. But that doesn't mean fashion girls can't find new ways to style plaid that actually feel fresh and current—and believe me, they do.
This season, I'm taking inspiration from some very cool girls on how to look totally fab in a plaid jacket, plaid skirt, plaid dress and (obviously) a plaid button-down. I'll walk you through it, if you'll let me.
The trick here is light-colored plaid: It's unexpected and adds dimension to the browns, dark blues, and grays in the rest of the outfit. Plus, the contrast trim is really beautiful and calls back to the bucket bag, so the whole look has consistency.
Heaven Mayhem
Esme Sunglasses
RAILS
Alps Cashmere Silk Scarf
Banana Republic Factory
Plaid Boucle Cropped Jacket
Matisse
Vancouver Bucket Bag
J.Crew
Nipped Straight Jeans
Mansur Gavriel
Ruched Loafers
I'm so sorry to tell you that this exact skirt from Miu Miu is sold out everywhere, but I have found a similarly colorful style that also has the advantage of costing a fraction of the price. Also, the exact coat is only available in Norway, but Atorie has a very similar style for ya.
Madewell
Demi Skinny Medium Hoop Earrings
Free People
Nova Long Sleeve T-Shirt
Phoebe Dynevor and Emma Watson are both loving plaid dresses this year, so I think it's safe to say it's a deeply cool choice. I love the understated yet universally chic color combo here.
Madewell
Single-Breasted Topcoat in Suede
Jenny Bird
Medium Staple Hoops
Jenny Bird
Monogram Necklace
Urban Outfitters
UO Kaelli Plaid Square Neck Cami Mini Dress
& Other Stories
Teardrop Wrap Ring
Quince
Italian Leather Pouch Crossbody Clutch in Cream
Calzedonia
Soft Comfort 30 Denier Microfiber Tights
Falke
Active Breeze Roll Top Socks
Thursday Boots
Penny Shoes
I wouldn't blame you if you associated plaid shirts exclusively with Pinterest style circa 2014, but I'm also somewhat delighted to show you that a simple but good plaid shirt with jeans remains a fantastic outfit in 2025 and 2026.
Pela Case
Honey iPhone 16 Pro Case
Chanel
Black Ceramic Diamond Ultra Wide Band Ring
H&M
Jacquard-Knit Sweater
Our Legacy
Dime Shirt Idaho Flannel Check
Acne Studios
Misubi Mini Shoulder Bag
Re/done
90s High-Rise Rigid Straight Jeans
Free People
Ruffle Sock Pack
Shopbop
Favorite Daughter Lola Croc Loafers
This outfit, come to think of it, really isn't all that fresh at all—it's deeply classic. It's also proof that you should never be afraid to lean into tried-and-true lines and color combos when it comes to your fall outfits.
