Comfortable, walkable ankle boots that feel like leather gloves

Everlane Day Boot, available at Everlane, $225

I wear these boots multiple times per week. They look great and go with pretty much anything, but it's their mix of all-day comfort and style that make them my default pair. The leather is buttery soft and fitted like a glove, the block heel low and walkable enough for my 40-minute walk over tough city concrete, and the sleek center seam is modern and lengthening. I wish they weren't $225, but they are worth the price, and I'd rather buy these than two inferior $100 pairs. — Mara Leighton, Insider Picks reporter

These are straight up the most comfortable boots in all the land. I have a pair in the cognac color, and I've worn them every day of this week and all throughout the fall — which is saying something, considering that I have approximately ten other pairs of ankle boots to choose from. They're as comfortable to walk in as sneakers. I kid you not.— Sally Kaplan, Insider Picks editor