With fall almost here, it’s time to ditch the sandals and bring out our favorite fall boots. Not only are they great shoes for stomping through fallen leaves, but they also play best with the blazer-and-jeans combo we so love to wear while sipping on a pumpkin spice latte. And there is one trendy style in particular we’ll be reaching for the most this season: square-toe boots.
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Whether you like them sleek black and knee-high or in buttery soft brown suede, square-toe boots feel like a return to the 1990s in the best way possible. For ones that feel modern and squarely set in 2025, however, there are a few things to look out for:
- They must have a square toe (obviously). The silhouette’s structured lines add elegance to any outfit.
- Also look for ones that are midi or knee-high length. That is, they reach somewhere between mid-calf and just below the knee.
- The heel should be wide and not too high. This season’s shoes are not about sacrificing comfort. Long live a sensible heel!
- They have a wide opening. The trendiest boots right now are not skin tight against the leg. You should be able to fit a pair of straight-leg jeans inside, for example.
We’ve seen square-toe boots presented at top designers like Alaïa, Stella McCartney, and Givenchy and in countless street style photos. It’s proof that square-toe boots are in the closets of the most stylish people we know. Luckily, retailers have picked up on this too so you won’t be hard-pressed to find a version that fits your personal style in stores.
Arguably, square-toe boots are more refined than round-toe ones, which can look a bit old-fashioned if their not styled in a modern way. And as much as we love the look of a pointed-toe boot, we have to admit that a square-toe is much more practical. They’re less prone to getting scuffed, which makes them a great choice to wear to work or on the weekends.
Put another way, square-toe boots offer a versatility that makes the most sleek and stylish option for the upcoming season. They’ll elevate a simple jeans, T-shirt, and blazer formula with the same ease as they would a long skirt and oversized sweater.
Dream Pairs Knee High Boots
Coach Harness Square Toe Boot
Jeffrey Campbell Hot Lava Boots
Franco Sarto Low-Block Ankle Boot
It seems everyone is ready to start wearing and buying these boots, too. We’re seeing them appear in countless Instagram and street style looks, and there’s been an influx of square-toe boots at retailers to meet the demand as well. Our advice? Don’t wait to pick up a pair—the season’s trendiest boots always sell out first.
