The Skinny Jean Style I Would Never Wear With Ankle Boots

Everyone has their own fashion pet peeves, but I feel like mine is one that should be shared with the world. Is it revolutionary? Probably not, but that doesn't mean we shouldn't be discussing it here. I have vowed to never wear skinny jeans that are too long with ankle boots. Why? Because the extra material tends to bunch awkwardly, and besides being uncomfortable, it's not the look I'm going for.
Instead, I always opt for an ankle-grazing pair of skinny jeans. This way, the jeans end right where your boots start, allowing for the most streamlined silhouette possible. There is definitely a time for lengthier skinny jeans, but in my opinion, ankle-grazing pairs are the best style to wear when you're searching for the most flattering denim-and–ankle boot combination.
Here, I have pulled some of my favorite ankle boot–and–skinny jean outfits from Instagram that prove semi-cropped (or at least particularly tailored) and ankle-grazing denim styles look the most flattering when paired with said boots. And don't worry—there's a large denim shopping selection ahead as well. We would never leave you hanging like that.
Go on to shop the ankle boot–and–skinny jean combination I always wear.
Style Tip: Go for an all-neutral look with a nude bodysuit, gray jeans, and some suede ankle boots. Add a chunky chain necklace for a bit of glamour and call it a day.
Style Tip: Let your new favorite coat do all the talking by layering it over your most basic pair of skinny jeans and ankle boots. Grab your favorite statement handbag and suddenly your everyday skinnies will feel like a million bucks.
Styling Tip: Don't let light jeans feel intimidating now that the temperatures are starting to drop. Instead, pair them with a bold sweater, chunky boots, and a structured coat for a fresh autumnal twist.
Style Tip: The easiest way to keep things easy yet interesting this fall is via a thin printed turtleneck. They are easy to style and clearly will look great with all of your go-to skinny jeans.
Style Tip: You can never go wrong with a classic Canadian tuxedo. With a crisp white tank and some trendy ankle boots, you'll have yourself a chic fall outfit in seconds flat.
Style Tip: Elevate your basics this fall with a pair of platform ankle boots, a dad hat, and a fuzzy coat.
Style Tip: Use your skinny jeans as a blank canvas for some fun new outfit experimentation this season. Take a cue from one of our favorite French girls and go bold with contrasting prints.
Style Tip: It doesn't get much simpler than black boots, classic denim, and a timeless beret. So the next time you have nothing to wear, reach for these pieces.
Next up, discover the 8 boot trends that are hitting their expiration date this fall.
Opening Image: Style du Monde
Lauren Eggertsen is currently the editorial director of Who What Wear and has worked at the company for over nine years, where she started as an associate editor and has since worked her way up. Lauren has worked in the Los Angeles and New York Who What Wear offices but currently calls L.A. home. Here, she leads and manages Who What Wear's editorial team and oversees all editorial content. Lauren's role also includes helping to set the fashion direction for all original photo shoots and often styles many celebrity cover shoots, including big names like Kaia Gerber, Normani, and Sabrina Carpenter. She has also attended multiple fashion weeks, including New York, London, Milan, and Paris, where her style has been featured on sites such as Vogue, Harpers Bazaar, and Elle.
-
I Just Created 5 Expensive-Looking Pre-Spring Outfits from Zara, Mango, and Nordstrom—You're Welcome
Outfits for everything from a wedding to brunch.
By Nikki Chwatt
-
Sunscreen Filters Abroad Are Totally Elite—Here's Why They're Not Available in the U.S. Yet
It's a bummer, but I have hope.
By Shawna Hudson
-
I Thought I Hated Skinny Jeans, But Kate Moss Just Made Them Feel Cool With This Shoe Trend
Suddenly I need a pair.
By Erin Fitzpatrick
-
So You've Heard Skinny Jeans Are Back—Here Are 6 Elevated Ways to Wear a Pair in 2025
Bring on the compliments.
By Jennifer Camp Forbes
-
Jamie Mizrahi's World: The Celeb Stylist's Favorite Red Carpet Look, Most Worth-It Shoe, and Album She Listens to on Repeat
A modern-day style expert.
By Allyson Payer
-
7 Extremely 2025 Trends I'll Pair With Skinny Jeans and Leggings to Make Their Return Less Scary
Who's with me?
By Allyson Payer
-
How Everyone Will Be Wearing Their Non–Skinny Jeans This Spring
Here's your outfit inspiration.
By Michelle Scanga
-
Suddenly, Women With The Row Style Are Breaking This Fashion Rule
You should too.
By Nikki Chwatt
-
We're Fashion Editors—Everything We Saw, Wore, Did, and Ate During NYFW
Let's dive in.
By Anna LaPlaca
-
New Yorkers Will Wear This Celeb-Concocted Ankle-Boot Outfit for the Next 3 Months
Sydney Sweeney just modeled it for us.
By Allyson Payer