Indeed, these leather boots may look rigid, but they're actually very supple. Plus, they come with Madewell's proprietary MWL CloudLift Lite padding in the sole for bonus cushion and comfort. These classic black, off -Comes in White, Deep Burgundy and Saddle Brown.

1. Madewell Leather The Rayna Boots

A lace-up style, both with the same lightweight lug sole and cushioned insole. And both are treated for water-resistance, so you can wear them in all kinds of weather without the stress of ruining that beautiful suede.

2. Hush Puppies Amelia Chelsea Boots

The sleek leather style comes with Margaux's signature padded insole that works to counter any pressure put on your arches by the 2.5-inch stacked heel. So if you're looking forward to wearing thick wool socks in the winter, you may want to go up to a half size.

3. Margaux Suede The Downtown Boots

If you're not planning on walking through the snow but still want to protect your feet from the winter chill, try these fleece-lined booties from UGG. But keep in mind they'll get wet when temperatures drop below 30 degrees. May not get warm enough for long outdoor excursions.

4. UGG Suede Lakesider Heritage Boots

The Dahlia style features a wide toe box, is supportive, durable and slip-resistant, although we often think of waterproofing for rain, snow or winter footwear, Dr. Cunha recommends this feature as often as possible Ho recommends to help prevent bacteria or fungus from growing in shoes.

5. Blondo Dahlia Booties

This gorgeous pair of classic tall boots from Naturalizer features a trendy square-toe. These boots also come in wider widths for those in the know. The heel is under 3 inches, but wide enough to counter any pressure on the balls of your feet. The footbed is also cushioned for comfort and to keep your toes happy all day long.

7. Naturalizer Leather Axel Boots

These rugged Chelsea boots come with an anatomically designed shock-absorbing Extra XRD footbed, which basically means they'll prepare you for a full day of walking, standing, and exploring. Front and back tabs make them easy to take on or off.

6. Leather Chelsea Boots

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