The 16 Best Square-Toe Boots to Buy This Autumn

Three fashion people wear the best square toe boot trend.

published 3 September 2025

The weather in London has been, well, let's just say varied, lately. In a single day, the skies have swung from 20+ degrees and sunshine to a hazardous downpour within seconds. There’s no denying that autumn is here and the days of strappy sandals and flimsy flats are well and truly behind us. Because of this, I’ve found myself looking more closely at boots again, namely my collection of bikers. Yet, as I scroll through my feed, there’s only one style the chicest people seem to be favouring a pair I don't yet own: square-toe boots.

Fashion person Sara wears the best square toed boots. She wears brown boots, a dark brown pinstripe trouser and dark brown top. She is smiling at the camera holding an umbrella in a recent image from her Instagram.

Like most things in fashion, the square-toe boot is something we've seen before. A core '90s shoe trend that you'll find on archival shots of everyone from Jennifer Aniston to Cindy Crawford, I also vividly remember my mum wearing a black leather pair slightly later in the '00s too. Still, the squared-off boot has stood the test of time and is just as relevant today as they ever have been.

Fashion person Aisha Farida wears best squared toe boots. She pairs her boots with corduroy brown jeans, a white tee and red and blue striped jumper. In an image in New York, she is stood looking into her bag in front of a big billboard and red brick buildings. This image was recently taken from her Instagram.

Arguably more refined than their rounded-toe counterparts which can look a little dated if not executed just so, yet far more practical than the pointed styles that are prone to stubbing, especially if you’re wearing them on your commute or when you’re clocking in a high weekend step count, the best square-toe boots offer a versatility that makes them a smart yet stylish choice for the season ahead. They elevate a simple trouser-and-tee combo with the same ease as a maxi skirt paired with a loose knit—both of which are outfits I live in when the seasons begin to shift.

An image from the Baum und Pferdgarten S26 053 Runway show featuring best square-toed boots. The model wears a shearling cardi, tan trousers and a hat. This image was take from Launchmetrics.

Now, it seems everyone is ready to talk (and wear and buy) boots again. In the last 24 hours alone, searches for women's boots have risen sharply by 100%. This is only made more noteworthy by the fact the market has had a sudden influx of boots in new-in sections, too. And if there's one thing I know, it's that the best boots always sell out early in the season.

Whether you're ready to commit or are just doing a bit of virtual window shopping, scroll on to see my edit of the best square-toe boots around.