The Fall Shoe Trend That Looks the Best With Skinny Jeans

September is almost here, and whether that's good news or bad news in your book, no one can deny the pleasures of fall shopping—especially fall shoe shopping. Per usual, we've been keeping a close eye on the fall trends since fashion week back in February, and a clear leader of the shoe pack has emerged: slouchy boots. Yes, the style you probably haven't worn since the early 2000s is back and better than ever. A slew of major designers (including Saint Laurent, Tibi, and Victoria Beckham) sent them down the runway with their fall looks, many of which featured skinny jeans.
You see, unlike many boot trends out there, slouchy boots actually look the best with skinny jeans, as they're roomy and provide a flattering proportional contrast to the slim denim style. Street style star Giorgia Tordini already took the look out for a spin at Paris Couture Week (shown above), and we predict that in a month's time, many other fashion insiders will join her. They look especially cool pulled down around the ankles and might even make you forgo your ankle boots a little more often than usual this fall.
To help you get ahead of the trend, we found 16 pairs of slouchy boots at a variety of price points to pair with your skinny jeans this fall. Shop our slouchy boot picks and see how a few designers paired them with skinny jeans below!
Shop Slouchy Boots:
Get the designer look (with a much more forgiving price tag).
We're in love with this rich color.
You'll want to wear these versatile booties every day.
Found: the white-boot trend 2.0. Next up, see the $50 H&M ankle boots everyone is buying.

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.
-
Cozy Cashmere! Sleek Suede! Dark Denim! 32 Affordable Fall Pieces You’d Find In A Wealthy Person’s Closet
Oh, did I mention they're under $250?
-
Dark-Blue Jeans Are Definitely "In" for Fall 2025, But so Is This Other Elegant Denim Wash
Trust us–you'll want to include it in your cold-weather wardrobe.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This Fall
It's all about this styling trick.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025
Exotic finishes! Sock boots! Western motifs!
-
There's No Question—These 8 Fall Shoe Trends Will Make You Look Rich
Luxe outfits are in your future.
-
These 32 Chic Zara Fall 2025 Shoe Finds Are the Key to Looking Like a Fashion Person—Good Luck Picking Just One Pair
Prepare for endless compliments.
-
Soft Knits and Suede Boots Are on My Mind—Here's What's in My Nordstrom Cart
Get in the fall mood with these chic picks.
-
Pump the Brakes on Booties—Kate Hudson Knows the Better Fall Shoe Trend to Pair With Dresses
This outfit combo is top-tier.
-
Give Your Denim Outfits a Chic Boost With These 21 Jeans From the Madewell Sale
Twenty percent off? Done and done.
-
7 Expensive-Looking Outfits to Wear With Fall's Most Iconic Shoe Trend
Let your outfit do the talking.