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

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.

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.

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.

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:

These would look just as chic with straight-leg jeans as they would with a maxi skirt.

A faux croc print boot is always a great idea when looking to add some texture to an outfit.

Staud

Wally 55 Leather Knee-High Boots

I own a pair of Staud boots and they're one of the most comfortable shoes I own.

& Other Stories

Leather Sock Boots

This is exactly the look I'll be channeling this autumn.

Reformation

Remy Knee Boot

Available in eight shades and patterns, you’re sure to find a Remy boot to suit you. I always recommend sizing up half a size in Reformation shoes.

ARKET

Square-Toe Ankle Boots

The perfect heel high for a day in the office to running to drinks.

Available in four shades, you’re spoilt for choice.

MANGO

Block Ankle Boots With Square Toe

I have a sneaky suspicion that this pair from Mango will sell out fast!

PARIS TEXAS

Bettina Suede Ankle Boots

The brown suede really elevates these jeans.

MANGO

Ankle Boots With Block Heel - Women

You know these boots went straight into my basket.

Staud

Wally 55 Leather Knee-High Boots

I own a pair of Staud boots and they're one of the most comfortable shoes I own.

AEYDE

Millie Leather Ankle Boots

A pair I can see myself still wearing in 10 years time, they’re that classic.

River Island

Brown Chisel Toe High Leg Boots

I’d pair these boots with a swing dress and blazer on a warmer day.

chl

Janis Over-The-Knee Boot

With an over the knee finish and soft leather draping on the foot, these feel like a wearable piece of art!

A square pointed toe and wearable trapezoid heel! If I won the lottery, there would be signs...

BRUNELLO CUCINELLI

Bead-Embellished Leather Ankle Boots

With a boho edge, these are the perfect boots to pull-on-and-go in the morning to elevate an outfit.