See the inspiration inside.
If there’s one boot trend that sparks debate every fall, it’s slouchy boots. Love it or pass on it, the oversize silhouette has reemerged this season. Instead of overthinking the volume or worrying about looking dated, the key is to treat slouchy boots like a statement piece and keep the rest of your outfit streamlined. Think of them as the exclamation point that instantly elevates a look, especially when paired with minimalist wardrobe staples.
The easiest way to lean in? Short hemlines. A minidress or micro skirt paired with slouchy boots creates a proportion play that feels effortless and cool rather than overwhelming. The looseness of the boot silhouette juxtaposed with showing some leg balances the drama, making the trend feel directional instead of intimidating. Opt for a clean-lined dress or a crisp miniskirt and simple top to ensure the boots take center stage without veering into costume territory.
Another no-fail formula is tucking skinny or straight-leg jeans into slouchy boots. Yes, it feels like a throwback, but when done with the right denim wash and sleek layering pieces, it comes across as modern and fresh. A sharp blazer, oversize leather jacket, or simple knit on top creates the polish you need, and the boots provide a nonchalant edge. It’s the kind of styling that proves even polarizing trends can look unexpectedly chic with the right execution.
Ultimately, slouchy boots thrive when styled with ease. Whether you’re pairing them with bare legs and a mini for a night out or slipping them over jeans on a casual day, the formula works because it embraces contrast—structured with slouchy, short with tall, streamlined with oversize. By sticking to these outfit equations, the trend transforms from divisive to desirable, showing that even fall’s most polarizing boot style can have a cool-girl moment.
See the easiest and coolest ways to wear slouchy boots this fall below and shop the styling essentials along the way.
Get the look: Cropped cardigan + Miniskirt + Belt + Slouchy boots
Z Supply Emile Cardigan
Astr the Label Laudine Skirt
RAYE Perla Boots
Get the look: Black jacket + Denim midi skirt + Short slouchy boots + Suede bag
BDG Dex Wadded Faux Leather Jacket
We the Free Come as You Are Denim Maxi Skirt
Free People Extra Slouch Boots
Get the look: Black elegant jacket + Silk scarf + Dark jeans + Black slouchy boots
Aligne Emily V Blazer
Pistola Beau Jeans
Schutz Mikki Cloak Boots
Get the look: T-shirt dress + Layered T-shirt + Slouchy boots + Leather bag
Free People Sinclair Sweater Minidress
ALOHAS Kalila Boots
Madewell Soft Grain Large Shopper Tote
Get the look: Striped polo shirt + Micro shorts + Slouchy boots
Moon River Striped Collar Pullover Sweater
Lioness Dollhouse Knit Shorts
Free People Kiki Kitten Heel Boots
Get the look: Black leather jacket + Oversize trousers + Black slouchy boots
BP Oversize Faux Leather Jacket
4th & Reckless Mira Trousers
Steve Madden Lytton Boots
Get the look: Black blazer + Minidress + Slouchy boots + Leather bag
Favorite Daughter The City Blazer
RAYE Liri Boots
Staud Mini Moon Bag
Get the look: Shirtdress + Baseball hat + Slouchy boots
Madewell Striped Tucked Mini Shirtdress
Polo Ralph Lauren Chino Sport Cap
Black Suede Studio Nev Boots
Get the look: Loose sweater + Miniskirt + Slouchy boots
Z Supply Sundance Sweater Jacket
Free People Paradise Found Vegan Skort
Madewell Lexie Knee High Boots
Get the look: Collared leather jacket + Black trouser shorts + Slouchy boots
Nordstrom Leather Shirt Jacket
& Other Stories Cotton Blend Bermuda Shorts
Frye Campus 12R Boots