Everyone in NYC Will Wear Jeans Tucked Into Boots This Fall

Women wearing boots tucked into jeans trend fall 2025.

(Image credit: @camillecharriere; @oumaymaboumeshouli)

published 17 September 2025

There's always a New York way to wear something, and this fall, it's all about jeans tucked into boots. After seasons of cropped hemlines skimming over ankle boots and straight-leg jeans paired with tall boots, the city's most stylish are flipping the script. Picture perfectly slouched denim slightly rumpled at the knees and cinched inside sharp leather boots—there's something effortlessly intentional about it. It nods to practicality for brisk walks across the city, but it also reads like an insider styling trick that feels directional.

The appeal is in the mix of polish and ease. Tucking jeans into knee-high boots instantly sharpens the silhouette, even if you're wearing the most broken-in denim in your closet. Structured boots give relaxed jeans a refined edge, while heeled pairs elongate the leg in a way that's understated but powerful. It's not about looking overly styled—it's about harnessing that balance of rugged and refined that New Yorkers always perfect.

Expect to see boots styled with everything from faded vintage denim to sleek indigo washes. Oversize outerwear—think trench coats, leather jackets, and boxy blazers—completes the look in a way that feels true to the NYC uniform. There's also a subtle functionality to the trend: Jeans tucked into boots keep hems clean on rain-soaked streets and add a layer of coziness when the temperatures drop. It's a style that makes sense with the city's rhythm, which is why it always catches on here first.

What makes this feel so new is the variety of boots hitting the scene. Tall Western silhouettes, moto-inspired riding boots, and classic pointed-toe stiletto versions are all in the mix, each bringing a slightly different energy to the tucked-in-denim formula. Pair slouchy jeans with sharp pointed boots for a fashion-forward effect, or lean into classic riding boots with straight-leg denim for a timeless look. However you do it, tucking jeans into boots is the fall styling move every New Yorker will be making, and the rest of us will be quick to follow.

See the fall outfit inspiration below and shop the key pieces along the way.