While there are technically only four seasons, I like to think that there's an unofficial fifth one that falls right between summer and fall. I present to you: boot season. It's the time of year when it's warm enough to wear shorts, dresses, and skirts but chilly enough to sport a pair of tall boots. As soon as boot season arrives in NYC, I always reach for my trusty Stuart Weitzman boots, and I'm definitely not alone.
My fellow fashion editor, Sierra Mayhew, has been a Stuart Weitzman loyalist since college, so of course we've bonded over how timeless and versatile its boots are. Her fall style revolves around the classics. "I'm leaning on trustworthy buys that always find their way back to my closet," she says. That's where the Stuart Power Knee-High Boot 75 ($850) comes into play. It's especially fitting this season, as Stuart Weitzman celebrates its 40th anniversary—and 40 years of the stretch construction that's become a signature of the brand—and the Stuart Power is one of the key styles in its fall 2026 collection. Sierra is already planning her early fall looks around this boot and giving us a sneak peek below.
"I've been known for my love of knee-high boots since my school days, and they're always one of my first purchases of the season. You simply can't go wrong when pairing them with anything and everything. I look forward to walking around Central Park and watching the leaves change or meeting up with a friend for brunch in this exact look come fall. Longer shorts are getting more and more popular, and pairing them with a knee-high boot is the ultimate styling move. I chose to style the outfit with my favorite cropped tee and a light trench coat. If you ever don't know what to wear but want to avoid being basic, consider this your go-to look." — Sierra Mayhew, fashion editor
"Fall in New York City will always have a special buzz because there's a back-to-school energy in the air. It makes for a lot of great parties and nights out, so I have a special wardrobe just for that. Given that it's the beginning of boot season, I love wearing a bubble minidress like this one to show off my favorite styles. These boots are perfect for a night out because they have a heel and are comfortable enough to wear on the dance floor all night. I decided to style this dress with silver jewelry and these stiletto boots. When you have a power accessory like this on hand, you don't need to add too much." — Mayhew
"I will be attending fashion week this fall, and this is the exact kind of outfit that would capture the attention of the best street style photographers. Timeless pieces like black knee-high boots, leather skirts, and leather jackets never go out of style. I've always known Stuart Weitzman to be a brand that dominates the footwear category, especially in the fall. The styles are so classic and timeless, with beautiful craftsmanship that means my boots will last for years. I expect to see this exact pair in my closet in 2036. The leather boots inspired me to wear leather from head to toe. The black leather jacket and matching boots looked even better with a contrasting skirt in between." — Mayhew
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