Square toe boots are a winter must-have: kick off 2025 with these 26 pairs

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Something you should know about me: I love square toe boots and own a few pairs. With its sleek and unexpected shape, the silhouette can quickly shift me into chic work mode or grunge moto boot territory, depending on my style. Based on trending Google terms, many of you also love the retro style: searches for “black square toe boots” and “leather square toe boots” are on the rise, as are other notable variations, like cowboy boots and knee-high boots.

From slim lace-up styles and micro heels for the office to western styles and chunky soles perfect for winter strolls, we’ve found the very best square-toe boots for the cold season. Just keep scrolling to find the exact silhouette that suits your style – or pushes it to the fashion limits!

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