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Fall Essentials: Boots, Clogs & Leather Sneakers

Cooler mornings, leaf-covered sidewalks, sweaters on repeat—this is your fall lineup. We curated cozy clogs, dress-casual leather sneakers, and wear-everywhere boots with walk-all-day comfort, traction, and easy styling for work, weekends, and travel.

Cozy Clogs

Slip-on ease + soft footbeds = peak autumn energy. Great with denim, flannels, and thick socks.

Leather & Dress-Casual Sneakers

Polished uppers, cushioned midsoles—made for the office-to-dinner shuffle.

Boots for Work & Weekend

From western silhouettes to everyday lace-ups, pick durable uppers and traction underfoot.

Wide-Fit & Roomy Toe Box

Use the Width filter for wide options; look for “roomy toe box” in product highlights.

Quick Care Tips

  • Brush suede before/after wear; spot-clean with a suede eraser.
  • Let cushioning rebound—rotate pairs during the week.
  • Air-dry insoles/uppers after long days to reduce odor.

 

404 products

Top Picks at a Glance

Model Support Cushion Weight Drop Wide?
Chelsea Ankle Boots TOPE520FLY MILITARY — — — — —
Chelsea Ankle Boots VAZE177FLY BROWN — — — — —
Chelsea Ankle Boots MEME030FLY CAMEL — — — — —
Chelsea Ankle Boots BUKI159FLY JAVA BLACK — — — — —
Buckle Ankle Boots YORT597FLY DUBLIN BLACK — — — — —
Zip Up Ankle Boots TULP592FLY OIL SUEDE BLACK — — — — —
Zip Up Ankle Boots MAZY323FLY OIL SUEDE BLACK — — — — —
Lace-up Ankle Boots RAMI043FLY RUG BLACK — — — — —

Comfort Score (1–10)

FAQs

Do I need stability?
If you overpronate or feel better with arch support, start with stability or motion-control models.

Can I use my own insoles?
Yes—choose shoes with removable footbeds and enough depth for orthotics.