Welcome to Word on the Street, a quarterly series in which one editor takes to the streets of New York City to snap her favorite fashion moments and shop them out just for you.
I can tell New Yorkers are ready for fall because even when the sun is sweltering, they’re committed to wearing a jacket. I don’t blame them—I’m eager to wear a few new favorite pieces, too, especially after photographing associate fashion editor Nikki Chwatt in her lineup of fall outfits from Free People. As much as I love summer, I feel less inspired by its wardrobe offerings. There’s only so much you can style with a dress and sandals. Fall is a much more interesting season for dressing, and Nikki’s outfits are proof. Funnel-neck, military-style, and faux-fur jackets are the stars of each look below, and Free People is doing them exceptionally well. To see how she styled these trending fall pieces, keep reading.
Which key pieces or styling details are you most excited to wear as we transition to fall?
I’m excited to bring funnel-neck jackets back into rotation. The high-collar silhouette is exceptionally flattering, visually lengthening the neck to build a sleek, streamlined shape. On top of that, its statement-making yet refined design naturally elevates even the simplest ensembles. While leather designs were everywhere last fall, I anticipate a shift toward sportier interpretations this season, which is why I love Free People’s Chelsea Jacket. Its cotton-blend fabric and relaxed bubble hem give it an easygoing, casual appeal, while the double zipper reinforces a subtle athletic vibe. The key to styling it in a cool, 2026 way lies in pairing it with unexpected pieces. So instead of jeans, try lace-trimmed shorts with pumps, a billowy maxi dress with closed-toe suede mules, or pedal pushers with kitten heels.
Free People
Chelsea Funnel-Neck Jacket
Free People
We the Free Atlas Boat Neck Top
Free People
Meet Me in the Middle Tap Shorts
Free People
Stella Round Sunglasses
What makes a great outerwear piece feel like an essential part of your fall wardrobe?
Fall is my favorite season to dress for because creating a chic look often comes down to elegant outerwear. Once you invest in a high-quality jacket with strong design details or rich textures, it becomes the outfit, instantly tying everything together with minimal effort. The Cloud Nine Ruffle Band Jacket is the perfect example. It works great worn open over a tank, but buttoning it up turns it into a top that only needs relaxed jeans or trousers and flats to make a look. Beyond its versatility, it fits right in with military jackets—one of fall 2026’s top outerwear trends.
Free People
Cloud Nine Ruffle Band Jacket
Free People
We the Free Luna Mid-Rise Straight Jeans
Jeffrey Campbell
Chezza Chelsea Boots
How are you styling denim and outerwear differently this season, and where do you envision wearing these looks?
A jacket-and-jeans outfit is my go-to in the fall. That said, I’m thinking about different ways I can style my favorite pieces and make them feel free. One way I plan to do so is with intentional accessories. I love the idea of wearing oversize sunglasses, whether a sleek, black, sporty cat-eye pair or a round, ’70s-inspired pair. I went the ’70s-inspired route with this outfit, styling the sunglasses with a faux-fur coat and ecru jeans. The Arlo sunnies added personality and made the Supernova Jacket feel directional. This is the type of outfit I’d wear to the office when I know I’m grabbing drinks with friends after work.
Free People
Supernova Cropped Faux Fur Jacket
Free People
Arlo Oversized Round Sunglasses
Free People
We the Free Most Loved Long Sleeve
Free People
We the Free Edie High-Rise Tapered Jeans
Jeffrey Campbell
Sweet Talker Snip Toe Boots