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This classic Chelsea boot is urban, laid-back and a smooth operator. Made of sleek black leather, with contrasting top-stitching, it’s your everyday go-to with jeans and skirts—and the perfect partner with your favourite funky tights. It slips on like butter, thanks to elastic gores on both sides and classic pull tabs in front and back. The low stacked heel is ultra comfy and stands up stylishly to long walks and long days at the office.

Maypearl Nala in Black ($170)

Made of soft, chocolaty suede, these boots are a delicious fall treat for your feet. Contrasting top-stitching and a leather heel accent give them a bit of cowboy cred to go with this season’s denim-obsessed looks. The stacked rubber heel and sole makes them a workhorse in any weather—their good looks and durable materials help them brighten up cool, grey November days.

Maypearl Daisy in Dark Brown ($170) 

Low-slung, with an easy retro vibe, these shorties are just right for autumn’s in-between days, when it’s too hot for your go-to tall boots. Made from luscious mahogany suede, with dark nubuck detailing on the heel, they’re a sweet, laid-back essential for kicking around with friends. The quick-zip side closure means they’re on, and you’re out the door in flash, looking every bit as cool as you feel.

Maypearl Juno in Mahogany ($160)

A little dressed-up but still chill, these booties add the height you want with a plush feel that’s easy on your soles. Smooth leather ankle straps crisscross over buttery mahogany suede, channelling an updated motorcycle sensibility. Sweet metal studs finish the look and add a bit of glam. Refined lug-style treads and rubber soles make these the best choice for chilly days with rain in the forecast—cozy and stylish, with no compromises.

Maypearl Alice in Mahogany ($180) 

Check out our roundup of fall’s hottest trends, then get shopping for these styles and more here.