The ’90s Are Calling! According to the Street Style Scene, a Flannel Shirt Is the Ultimate Transitional Wardrobe Staple

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It’s not uncommon that a humble closet classic gets a full-fashion makeover at the dawn of a new season. Just this fall, we’ve seen refreshes to flared jeans (Chloé with two-toned denim), white button-downs (Loewe with a built-in statement belt), and blazers (collarless at Toteme, suede and bejeweled at Miu Miu). We’d argue that there’s one more staple worth adding to this list of old favorites revisited: a checkered flannel shirt. Yes, the layering essential whose heyday harks back to the grunge and club scenes of the ’90s is back and better than ever with a more fitted shape and softer color palette from the likes of Róhe, Toteme, and Bottega Veneta. Just in time for apple-picking season, try six flannel shirt outfits that have the runway and street style scene of approval.

The Layering Essential: Polo Ralph Lauren checked cotton-twill shirt, $170
The Fall Fashion Find: Róhe checked cotton-flannel shirt, $350
The Minimalist Model: Toteme checked linen-blend shirt, $680
The Go-To Grunge: Our Legacy Apron checked and striped cotton-flannel shirt, $383
The Catwalk-to-Closet: Bottega Veneta checked crepe shirt, $1,600
The Overshirt Offering: Buck Mason Baywood shadow plaid overshirt, $188
The Dainty Delight: Dôen Joelle top, $198
The Cashmere Choice: Guest in Residence checked cashmere shirt, $685
The Borrowed-from-the-Boys: Frame Baja plaid shirt, $268
The Rodeo Ready: J.Crew Western shirt, $118

Dressing for the transitional season can be notoriously tough to navigate. On any given September day, temperatures can range from a balmy 80 degrees to a crisp 60 the next, calling for a tried-and-true layering essential that can be easily taken on and off in style. During New York Fashion Week, flannel shirts were the transitional staple of choice with It girls and models off-duty sporting theirs with everything from sleek black jeans or leather trousers to shin-grazing midiskirts and even Bermuda shorts. Courtney Grow put her red-and-white plaid pick on display, draping it casually over a plain white tee and pairing it with wide-leg burgundy trousers from Loulou Studio. Then, there was a seriously chic show-goer outside the Toteme spring/summer 2025 presentation, who styled hers with a straight-leg white jean and pair of pointed-toe smoking loafers. You could even tie yours around your waist alongside other go-to basics for a more subtle nod to the top fall trend.

Below, allow the street style scene–and these six flannel shirt outfits–to help you tackle the transitional season in style.