I Live in Skinny Jeans and Black Ankle Boots—Here Are My Favorite Outfits

I recently dove into one of the biggest workhorses in my wardrobe—black skinny jeans—and highlighted my favorite outfits featuring the trend. But after thinking about my daily uniforms further, I realized that my black boots also hold just as much significance in my wardrobe as skinnies. And when you combine the two—black skinny jeans and booties—well, that’s just the start of a perfect outfit in my opinion.
The rest of the fashion universe must agree with me because the style elite consistently posts forward ensembles on Instagram featuring the two closet staples. Their looks are too good not to share, so I'm showcasing the coolest outfits with skinny jeans and black ankle boots of the moment, along with the best silhouettes to shop now. Trust, I’ll be copping a few (if not all) of what’s coming ahead.
A blazer and a chunky knit bring instant polish to light-wash jeans and boots.
Highlighter hues are everywhere this season—and pop flawlessly against black jeans.
Allow a cool statement top to be the hero piece of an all-black 'fit.
While simple, a white knit, long coat, black jeans, and ankle boot look is extremely elegant.
For a downtown vibe, don't underestimate the power of a moto jacket, cropped jeans, and boots ensemble.
While featuring only a few pieces with the leopard top, skinnies, and booties, this vibe still feels high-concept due to its statement nature.
If skinnies and boots are your thing for travel, try them with a tee and slouchy blazer for a comfortable yet elevated look.
Next, check out how Jessica Biel wears skinny jeans.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday Wear
Effortless, easy, and cool.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025
Exotic finishes! Sock boots! Western motifs!
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do Too
See how fashion people from NYC to Paris to London wear them for fall.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to Her
A glimpse into the life of this savvy entrepreneur.
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in Fall
And you probably already own it.
-
There's No Question—These 8 Fall Shoe Trends Will Make You Look Rich
Luxe outfits are in your future.
-
The Easy-Yet-Elevated Outfit Formula Fashion People Will Be Wearing Straight Into Fall
Here are seven takes on the chic look.