50 Of My Favorite Shoes For Fall-Winter 2024

Footwear options across 7 cold weather categories to help you strut stylishly (and comfortably) through the next few months.

The sun-soaked days of wearing sandals and breathable canvas sneakers are well behind us, so it’s time to start thinking about which shoes will help you walk gracefully —and comfortably— through the coldest months of the year. See, as is the case with most items of clothing in your foul weather wardrobe, the best fall-winter shoes require considerations beyond just style. Don’t get me wrong—stuff that looks good is always going to be at the top of my priority list—but point is your footwear should also do at least a reasonable job of keeping your dogs in working order, too.

As such, below I’ve selected 50 pairs of shoes across 7 footwear categories specifically tailored to this time of year, including: lug sole loafers, hiking boots, moc toe boots, dress boots, lug sole boat shoes, lug sole derbies, and vintage options.

Now, I’m not saying you need to get one pair from each section to build a worthwhile rotation, but the idea is to make it as easy as possible to curate an arsenal of shoes that’ll last from now until spring—whether you’re doing some suited-up strutting around the city and are simply trying not to eat shit, or find yourself in a winter wonderland far off the beaten path. Let’s get to it, and as always, enjoy!!!

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