The 28 Best Square Toe Boots

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Okay, I love a square-toe boot and own quite a few pairs (as you can see!). The shape is just so sleek and unique and can either bring me into chic work shoe mode or grunge combat boot territory. And our collective Google search history implies lots of you love the retro-esque style: Searches for “black square toe boots” — especially “square toe cowboy boots” — are surging as are other notable variations, such as classic knee-high boots. It’s why we couldn’t help but compile all the best styles in a comprehensive guide for you.

From lace-up booties and cowboy boots (hello, fall 2023 boot trends) to skin-tight silhouettes and micro heels (hey there, 2024 top shoe trends), we found the very best square-toe boots. Just scroll on to find the exact boot that matches your personal style — or that pushes it to the fashion limit!

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