These Easy Outfit Formulas Make Even Fall’s Most Polarizing Boot Trend Look Cool

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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.