What could be more simultaneously comfortable and cozy than fleece-lined Doc Marten Cheslea boots?
I don’t think anyone should worry about aging out of wearing high tops, especially when they’ve got a simple, straightforward color and design like these Vans do.
These kind of resemble moon boots, which I choose to view as a plus.
I never quite understand when I see people wearing these shearling-lined Birkenstocks outdoors on cold days—don’t their heels get chilled?—but they’d be excellent for padding about the house.
Classic black Supergas with a nice thick sole for added height.
I have an earlier version of these Nikes from a few years ago, and they’re the best, most comfortable shoes for those early morning dog walks I’m always bitching about.
These Tretorn rain boots are practical as they are cute, and I dig the blue and red pull tabs.
I showed you these Vince boots—which look like a chic-ified version of Red Wings—not that long ago, but they fit so well in this category that I’m doing a repeat. I don’t often like a white sole on a dark shoe, but these really work somehow.
You can’t beat a timeless pair of Converse All-Stars, and the wee purplish stripe is a winning touch.
This shearling-lined ankle boot from Mansur Gavriel comes in a few colors—including a very cool pale pink—and it’s so appealingly clean-lined.