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.
Get the look: Blazer + T-shirt + Jeans + Western boots
Get the look: Long white scarf + Polished black top + Jeans + Slouchy boots
Get the look: Loose blazer + Sweater + Black jeans + Printed boots
Get the look: Bright jacket + Loose dark jeans + Black pointed-toe boots + Colorful bag
Get the look: Long coat + Black turtleneck + Black jeans + Black riding boots
Get the look: Cropped trench coat + Baggy jeans + Belt + Slouchy boots
Get the look: Long-sleeve T-shirt + Black skinny jeans + Leather belt + Tall black leather boots
Get the look: Oversize trench coat + Baggy jeans + Pointed-toe leather boots
Get the look: Zip-up jacket + Loose jeans + Slouchy boots
Get the look: Blazer + Zip-up sweater + Skinny jeans + Western boots
Get the look: Chunky sweater + Distressed jeans + Leather boots
Get the look: Striped shirt + Baggy jeans + Slouchy suede boots
-
For the Skinny-Jean Skeptics, This Is the Compromise Silhouette to Try This FallSo flattering and very versatile.
-
I Walk Over 5 Miles A Day Working in Manhattan—Here’s an Editor-Approved City Girl’s Guide To Fall ShoesPlus, how I'd style them.
-
Forget What You've Heard—Ankle Boots Are Still In, and This Expensive-Looking (But Just $50) Pair Is ProofGrab them before they're gone.
-
I Know Good Jeans—Here Are 5 Pairs for Fall, Plus the Perfect Sweaters to Wear With ThemThe perfect duo.
-
Wearing a Preppy Cardigan With This Controversial Boot Trend Makes It Look 10x CoolerYou won't believe it.
-
I'm Building the Boho-Chic Closet of My Dreams—31 Fall Finds From Free People and Anthropologie That Fit the BillLet's talk about micro shorts and Western boots.
-
Jeans, Who? It Girls Everywhere Are Wearing Boots With This Anti-Denim Trend Right NowIt will also be a fashion person's go-to uniform this winter, too.
-
I'm a Senior Shopping Editor—These 25 Elevated and Rich-LookingReplica Store Fall Sale Picks Have My AttentionChic and affordable? Yes, please.
