When we think about the shoe of the season for fall, one word immediately comes to mind: boots. From Chelsea silhouettes to slouchy suede, nothing says “autumn in New York” quite like a good pair of boots. Some might even say Marc Fisher has mastered the art of the comfortable boot, the kind you can wear for 10,000 steps between West Village vintage shops and your favorite pumpkin spice latte stop. So when we heard the girls were out showing off their boots this season, we had to hit the streets to see how they’re styling them. Here’s our official Fall Boot Coverage, straight from the city sidewalks, with a little help from Marc Fisher.
It’s officially suede season, and the Naples Boots are proving it. She’s styling the fold-over silhouette with an oversized olive utility coat and a matching mini skirt, finishing the look with a rich brown leather handbag. The combination of olive and brown makes for the ultimate fall color story, earthy, tonal, and effortlessly chic. It’s the kind of outfit that feels like walking through Central Park in late October, cozy but elevated.
Jamie Alanna Bloom is the Public Relations Coordinator at OOTD. Her experience spans editorial styling and writing, seasonal campaigns, and behind-the-scenes design work, all rooted in a deep love for fashion. She’s especially fond of subtle elegance, and a classic ballet flat, along with the power of a well told style story. She graduated from Syracuse University, and brings a fresh, trend-aware perspective to brand communication and media strategy.
She’s paying homage to the month itself in this look. An orange crepe blouse paired with a sleek black midi skirt creates the perfect fall contrast, while the Esmee Boots in dark suede tie everything together with a refined touch. Accessories matter here, a brown buckle shoulder bag and oversized sunnies make this the quintessential “pumpkin spice meets city edge” outfit. We’re taking notes on this one for the perfect transitional color palette.
Rock-core style is having its moment, and she’s proving just how wearable it can be. The Esmee Boots in black suede bring structure and edge to her look, paired with a coordinating black leather coat. She’s tucked two-toned jeans into the boots for that effortless, model-off-duty feel. A black slouchy bag and oversized sunnies seal the deal, it’s edgy, sleek, and unmistakably downtown.
Yes, you read that right: skinny jeans are back, and she’s here to make her case. She’s styling a dark-wash pair with the Lannie Boot, creating a clean, elongated silhouette. Up top, an off-the-shoulder black top adds balance, and the look is completed with a wide-brim hat that screams downtown cool. She’s not just wearing the outfit, she’s owning the street she’s walking on.
A black leather boot and lace mini shorts? A dream pairing. She’s styling the Lannie Boot again, but this time for a night out on the town. A sequined knit top layered over a black bralette gives the outfit a touch of glam, while a black leather coat keeps it grounded. It’s the kind of outfit that makes you want to text your friends: “Drinks tonight?”
Sometimes, less really is more. She’s letting the boots take center stage here, wearing the Naples Boot with a simple black mini tee dress and a classic nylon shoulder bag. No frills, no fuss, just sleek, understated style. The suede folds perfectly with every step, adding just enough texture to make a minimal outfit feel intentional and refined.
Nothing says “fall in New York” quite like plaid, and this look delivers. She’s wearing a classic plaid mini skirt with the Esmee Boot in black leather, creating that balance between preppy and downtown chic. On top, she layers a taupe leather racer jacket over a warm tan turtleneck — cozy, coordinated, and completely trend-forward. It’s a look that belongs somewhere between a coffee date and a gallery opening.
