New Yorkers Will Wear This Celeb-Concocted Ankle-Boot Outfit for the Next 3 Months
If you're feeling like we're in a bit of an ankle-boot dry spell, you're not wrong—especially as far as celebrities are concerned. Knee-high boots and flats have reigned supreme this season, but that doesn't mean ankle boots are out by any means. It's a staple shoe style that we all own. On that note, there's some new ankle-boot outfit inspiration courtesy of Sydney Sweeney.
Sweeney has been spending a lot of time in NYC to film The Housemaid, and she packed a NYC cool girl–coded wardrobe to see her through her time there. The fact of the matter is that East Coasters have a few more months of winter to contend with, and that amounts to a lot of outfits to choose. While out on a rainy night in the city, Sweeney was photographed wearing an ankle-boot outfit that makes the boots look fresh, NYC-appropriate, and very 2025. She wore a fitted black leather jacket layered over a camel sweater with a leather miniskirt, sheer tights, and black leather combat boots with a sock-like fit. I don't know about you, but I'm newly inspired to wear some leather on leather with my ankle boots. Keep scrolling to join me and shop similar pieces to Sweeney's and a few ankle boots I think you'll be into.
On Sydney Sweeney: McQueen jacket, sweater, skirt, bag, and sunglasses
Get the Look
Shop More Cool Ankle Boots

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
Looking Stylish This Fall Means Wearing Your Pretty Dresses With This Unexpected ItemHere's how to master the look.
-
Here's the Comfy Yet Incredibly Chic Boot Style Fashion People Are Already Wearing on RepeatThese make any outfit look more expensive.
-
If You're Going to Wear Sweats This Fall, Please Only Wear Them Like This, This, and ThisOutfits that look truly elevated.
-
Chicer Than Jeans and a T-Shirt—Everyone With Rich Taste Will Wear These Denim Outfits This FallYour new uniform to elevate your style.
-
Not Skinny Jeans, Not Leggings—Everyone With Good Taste Is Wearing Boots With This Fall Staple InsteadThe chicest outfit formula of the season.
-
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.
-
This "Ugly" Shoe Trend Is Officially Back From 2016—But This Time, It's BetterSpotted in London and NYC.
-
This Is the 2025 Way to Wear the Ankle Boot Trend Everyone Bought 4 Years AgoPSA: Don't toss them yet!

