The spring 2026 New York Fashion Week shows have officially ended, and the city-dwelling street style scene always teaches an in-real-life lesson on versatility, layering, and, surprisingly, comfort. While the colder months are all about heavy-hitters (wool, fleece, and cashmere), the fall season is all about lightweight transitional staples that can be worn until the last leaf drops.

The NYFW Street Style Guide to Transitional Outerwear

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The Cropped Denim Jacket

Rùadh The Mhor cropped denim jacket

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New Yorkers are masterful at adaptability—at the drop of a hat, the city must be ready for a post-work event, a detoured route home, a last-minute dinner plan, or a sudden rain storm; one never knows! As versatile as the people themselves, transitional outerwear has become a cornerstone of New York Fashion Week street style. Showgoers this season embraced those wear-with-anything layers, like the suede blazer, the barn jacket, and the luxe leather bomber. There’s even the funnel-neck jacket, which has been popping up as often on the runways as it has on the attendees.

From denim jackets to classic blazers, here are our favorite transitional street style looks to re-create—all anchored around one key piece: a great piece of outerwear.

Photographed by Phil Oh

The Leather Bomber Jacket

Spotting a leather jacket in New York, especially during Fashion Week, is to be expected. But this season, we’re seeing the staple in new, rich hues, like oxblood and lived-in chocolate brown. Wear yours as the foundational piece with grey, pleated trousers.

Photographed by Phil Oh

The Suede Blazer

The sumptuous suede blazer has emerged as a hero item the past few seasons. Fall back on this seasonal favorite in a versatile camel hue that’s borrowed from the boys and use yours to top off a classic button-up shirt and funky denim story.

Photographed by Phil Oh

The Barn Jacket

Countryside codes, such as corduroy and twill, receive a modern update when contrasted by unexpected separates. Here, add levity to the everyday with a sequined midi; when paired with a workwear-inspired chore coat and white tee, it makes the overall look feel decidedly less precious.

Photographed by Phil Oh

The Denim Topper

There’s never a wrong time for a denim-on-denim pairing. Play around with proportions to give the Canadian tuxedo a new lease on life, as this stylish showgoer demonstrated with her oversized jacket, folded over at the waist, and straight-leg jeans in a lighter denim wash.

Photographed by Phil Oh

The Oversized Black Blazer

No well-curated wardrobe is complete without a blazer, or two. Follow Naomi Elizée’s lead and pair a roomy style and over a simple white T-shirt, then add texture and femininity back in with a lace-trimmed silk short.

Photographed by Phil Oh

The Cropped Trench Coat

The traditional, rainy-day trench gets a new look for the season with a little trim. Take cues from this street styler and style yours with a lace-trimmed dress and sharp accessories.

Photographed by Phil Oh

The Funnel-Neck Layer

Brands, like Victoria Beckham, Chloé, Khaite, Stella McCartney, and Gabriela Hearst, have embraced the funnel-neck jacket as a sophisticated option for everyday dressing. In this look, less is better. Wear yours with slim-fit jeans (skinny pants are back!), and a playful silver sneaker.