8 Flannel Shirt Outfits to Tackle the Transitional Season in Style

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Plaid and checks are here to stay for another season—the spring/summer 2026 shows made that abundantly clear, with Chanel, Acne Studios, Dior, and Tod’s all incorporating grid-like patterns into their collections. For fall, flannel (a perennial favorite) continues to shine. Once a staple of the grunge and club scene of the ’90s, this season the fabric takes on a more refined form—fashioned into tailored and draped silhouettes and reimagined in unexpected colorways.

A great layering piece no matter how styled, flannel moves effortlessly through shifting temperatures and settings. This past Fashion Month, It girls and models off-duty proved its versatility, wrapping it around the waist of jeans and pairing it with leather trousers and shin-skimming midi skirts. For more ideas on how to wear flannel right now (plus our favorite styles to shop), keep scrolling for eight outfit ideas built around the fall essential.

Vogue’s Favorite Fall Flannel Shirt Finds:

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The Wrap Shirtdress

Banana Republic flannel tie-front shirt dress

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The Heritage Print

Burberry relaxed fit checked flannel shirt

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The Relaxed Button-Down With White Jeans

A crisp pairing that never fails: a flannel shirt and white denim. Layer a gray turtleneck or a perfect white tee underneath, or knot the flannel around your waist for a more relaxed touch. Finish with black loafer boots and delicate huggie earrings for a minimal yet refined look. As with any wardrobe essential, the styling possibilities are endless.

The Tunic and Denim Midi Skirt

Lean into western sensibilities by pairing Banana Republic’s tunic-style plaid shirt over a flared blue denim skirt. Ground the look with suede harness boots for a modern take on cowboy-meets-city styling.

The Oversized Shirt With a Silk Midi

Want a cool, yet dressed-up take on plaid? Opt for Cos’s neutral plaid shirt and a butter yellow midi for a feminine twist. Pair this look with JW Anderson’s loafer mules and timeless gold hoops. Complete with a bucket bag for day or a black clutch for an evening out.

The Soft Color Combo With Dark-Wash Denim

Western boho meets downtown cool in this outfit idea primed for an off-duty moment. Start with Róhe’s blush and orange-toned flannel and Khaite’s dark-wash denim then top off with DVF’s duster fringe jacket and a Prada buckle bucket bag.

The Abstract Motif With a Sheer Skirt

Zara’s yellow-brown-blue flannel brings a fresh, modern feel. Tie it loosely around your waist and pair with this season’s must-have sheer skirt. Add high vamp studded ballet flats to strike the perfect balance between edgy and effortless.

The Cashmere Overshirt With a Draped Midi

Who doesn’t love cashmere? The luxe fabric plays well with other sophisticated pieces, like a draped skirt, kitten heels, and Chanel’s iconic wrap watch. The end result is a blend of outdoorsy cool and urban polish.

The Checked Shirt With Corduroy Pants

Corduroy has made a full-fledged comeback this fall. Chanel The Row’s influence by pairing an olive green pair with Proenza Schouler’s checked shirt and Sophie Buhai’s moon pendant necklace. Shearling-lined loafer mules add a touch of cozy comfort for cooler days.

The Oversized Check Shirt With Pleated Culottes

Throw a roomy plaid shirt unbuttoned over a simple white tee; instead of jeans, opt for pleated culottes and leather riding boots for a subtle nod to equestrian style.