It’s not uncommon for classic wardrobe staples to get a fashion makeover with the arrival of a new season. This fall, we’ve seen reinventions of flared jeans, white button-downs, and blazers. But there’s one more essential worth adding to this list of old favorites revisited: the checkered flannel shirt. This layering essential, reminiscent of the grunge and club scenes of the ’90s, is back and better than ever with a more fitted shape and softer color palette, as seen in designs from Róhe, Toteme, and Bottega Veneta. Just in time for apple-picking season, let’s explore six flannel shirt outfits that have the approval of both the runway and the street style scene.
Dressing for the transitional season can be a challenge. One day it might be balmy, the next crisp. A reliable layering essential that can be easily added or removed is crucial. During New York Fashion Week, flannel shirts were the go-to transitional piece, sported by It girls and off-duty models alike. They paired them with everything from sleek black jeans and leather trousers to midi skirts and even Bermuda shorts. Courtney Grow showcased her red-and-white plaid pick, casually draped over a plain white tee and paired with wide-leg burgundy trousers from Loulou Studio. Another chic showgoer outside the Toteme spring/summer 2025 presentation styled hers with straight-leg white jeans and pointed-toe loafers. You can even tie a flannel around your waist with other basic pieces for a subtle nod to the top fall trend.
Let’s dive into the street style scene and explore six flannel shirt outfits that will help you conquer the transitional season in style.
Get Creative With Your Layering
Influencer Courtney Grow’s signature style is both pared-back and playful, with outfit ideas that are easy to recreate. Her latest look on the NYFW streets was no exception. She layered her red and white flannel over a plain white tee, luxe leather trousers, and mesh ballet flats. Follow her lead and throw it over your shoulders or tie it around your waist. As with any elevated essential, the styling possibilities are endless!
Out West We Go!
The plaid shirt joins other Western wear items like cowboy boots, flared jeans, and suede jackets, that have taken on a new fashion life this season. Like this New Yorker, sport Róhe’s slate gray flannel, featuring an exaggerated collar and slim-fitting silhouette, with straight-leg black jeans and off-white Bottega Veneta mules. The Row’s palm-shaped day clutch adds a touch of elegance to the look.
From Catwalk to Closet
Toteme’s blue-and-yellow checked flannel debuted last season and has since become a staple in many It girls’ capsule wardrobes. Outside the Copenhagen-based brand’s presentation during NYFW, one showgoer sported hers with a go-to white jean, pair of smoking loafers, also from Toteme, and a slouchy hobo bag. Consider this your new signature look for off-duty occasions.
Some Fits Are Best Borrowed From the Boys
Vogue’s own, Naomi Elizée, is known for making a sartorial splash, and her latest flannel shirt outfit is no exception! Steal her style with Balenciaga’s menswear-inspired, oversized shirt, tailored Bermuda shorts, and Maison Margiela’s knee-high Tabi boots. A charming tote, also from Balenciaga, is hard to miss, as are Elizée’s statement aviator sunnies.
The Flannel Shirt, But Make It a Blouse
Want the cool, yet casual vibe of a flannel shirt, but with a feminine twist? Opt for Mango’s asymmetrical checkered blouse instead. Style it with Joseph’s houndstooth midiskirt and leopard-print ballet flats from & Other Stories for a print clash masterclass. Banana Republic’s studded leather belt adds some edge, while classic black accessories from Dragon Diffusion and Cos keep things timeless.
Just a Touch of Flannel
According to this stylish New Yorker, you don’t have to wear a full flannel shirt to appreciate the trend. Instead, tie a scarf or top around your waist alongside other chic separates, like a polished blue button-up, metallic leather midi skirt, or a pair of camel-colored ballet flats. This adds a touch of playfulness and fall festivity to a seasonless look.
