Slouchy boots have a longer story than the Noughties revival suggests. Vivienne Westwood showed her Pirate collection for autumn/winter 1981, and the soft, wrinkled boot that came with it is still the shape most slouchy boots borrow. Kate Moss and Sienna Miller made them a 2000s uniform, and Vogue has since called slouchy boots fall's status shoe. I think they are back because they are the opposite of a stiff, perfect boot.

 

The scrunch is the whole point, so start with the pairs that do it best. Silent D's Heidi, in two colours, and its Heev and Hervee fold softly down the leg, and Kelsi Dagger's Brooklyn and the By Anthropologie Suede Scrunch are the easy everyday ones. Jeffrey Campbell's Doubloon and Frye's Shiloh fold over at the top, so you can wear them high or low, and Dolce Vita's Buckly brings in a western toe.

 

Amina Muaddi's Anok and Isabel Marant's Rilton, both in suede, are the pairs I would keep for years. Schutz's Mikki Up Cloak and Harriet, Michael Kors's Dawn and Vince Camuto's Sorina and Genisa are the ones I would wear to work, Bibi Lou's Peggy is the softest tall pair, and Steve Madden's Bozeman, Earth's Venla and Jessica Simpson's Paeril add a cuff, whipstitching and a buckle.

 

The test I use: push the shaft down with one hand. If it gathers into soft folds and stays there, it is a slouchy boot. If it springs back up, it is just a wide boot.

 

What I would skip: a wide-leg trouser tucked into a slouchy boot. The slouch needs a slim line above it, so wear it with a straight jean, a slip dress or bare legs.

Not every slouchy boot has to reach the knee. Schutz's Maryana is the one I would start with, and By Anthropologie's Ruched Riding and Bibi Lou's Isolde keep the shaft tall but soft. Seychelles' Westlake is the mid-calf scrunch I would wear with a midi skirt.

 

For something shorter, Jessica Simpson's Komoena, Vince Camuto's Grenna, BCBG's Dinay and Steve Madden's Elora are ankle booties with the same gathered shaft. The kitten heels are the prettiest here: By Anthropologie's Ruched Kitten-Heel, Nine West's Sawyor and Marc Fisher's Dalores.

 

Steve Madden's Aldora and the By Anthropologie Slouchy Western lean cowboy, Jeffrey Campbell's Tabi Herring has the split toe, Seychelles' Getty sits on a wedge and Madden Girl's Elite goes over the knee. The looser the boot, the slimmer I like the trouser or skirt above it.

The mistake with slouchy boots is trying to make them neat. Let the folds fall where they want, and keep everything above them simple: a slim jean, a short dress, a long coat.

 

If you only buy one pair, make it a tall suede boot in black or brown with a low heel. It goes with most of what you already own, and the shape has been coming back since 1981. If you want to keep browsing, I also put together Khaite Boots Dupe and Boots 2026.