Square-Toe Boots Are A Winter Must-Have: Step Into 2025 In These 25 Pairs

Something you should know about me: I love a square-toe boot and own quite a few pairs. With its sleek and unexpected shape, the silhouette can quickly bring me into chic work mode or grunge moto boot territory depending on the style. Based on trending Google terms, lots of you love the retro-esque style as well: Searches for "black square toe boots" and “leather square toe boots” are surging as are other notable variations, such as cowboy boots and knee-high boots. 

From slim lace-up styles and micro heels fit for the office to Western styles and chunky soles perfect for gallivanting through the winter landscapes,  we found the very best square-toe boots for the cold-weather season. Just scroll on to find the exact silhouette that matches your style — or that pushes it to the fashion limit!

If, like us, you carted up a pair of pink or metallic cowboy boots this past summer for Taylor Swift's Eras Tour, and have since worn them on every night out since, you'll be excited for this trend: square-toe Western styles that will have you channelling Cowboy Carter. (Rumours are Beyoncé is planning a new 2025 tour after her “Beyoncé Bowl” performance so we've got to be ready). Go for genuine, sturdy cowboy boots from brands like Ariat and Frye for a timeless, rustic pair or buckled moto styles to hone in on the Western fashion trend in a more subtle way.

Ankle boots are a wardrobe staple — in particular, square-toe ankle boots, which offer an extra edge thanks to their unique shape, whether they're on the chunkier or the slimmer side. We love a tried-and-true leather boot with short block heels (extra points if the heels are angular), which are a sturdy option for the winter. But you can also find this boot shape with dainty kitten heels or on-trend animal prints for more upscale occasions. 

Everyone needs a pair of knee-high boots. The versatile shoe simply looks great with mini dresses and tights, midi skirts, or even tucked under wide-leg jeans for extra warmth. Whether you're looking for a platform or a sleek stiletto, there are plenty of square-toe boots to choose from. You can go as bold or tame as you want, playing with fabric, colour and heel shape.

If you’re on the hunt for office-appropriate square-toe boots, you can’t go wrong with a pair of polished ankle boots. On work days, I regularly reach for my Vivaia square-toe boots (which I have in multiple colours) because of their soft sock-like fabric and comfortable block heels. But you can also opt for a higher heel or knee-high length depending on your work’s dress code.

For lace-up boots, you can either go for a chunky combat pair or a delicate Victorian style. I personally can get behind both depending on the outing and outfit. But, no matter which way you sway, you're bound to look stylish and feel super-empowered to stomp into the new year in these square-toe boots.