The Timeless Boot Style People With Chic Taste Quietly Favour Over Round-Toe Pairs

Boot trends come and go, but one that always seems to endure is that of the square toe. Scroll on to find out why this is and to see the chicest pairs of the season.

Three fashion people wear the best square toe boot trend.
(Image credit: @_livmadaline@styledsara@aishafarida)
Imani-Nia Francis-Tsolaki's avatar
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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.

(Image credit: @styledsara)

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.

(Image credit: @aishafarida)

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.

(Image credit: 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.

Shop the Best Square-Toe Boots:

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Imani-Nia Francis-Tsolaki
Imani-Nia Francis-Tsolaki
Junior Fashion Editor

Imani-Nia Francis-Tsolaki is Junior Fashion Editor at Who What Wear UK, where she expertly navigates Gen-Z-aligned editorial content and brand try-ons to unearth the most worthwhile pieces, while valiantly resisting the urge to add every single one to her basket.

At Who What Wear, Imani is committed to uncovering cool new brands to share with the WWW UK readership, and finding gems that make shopping accessible (and fun) for everyone.

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