Boot season is officially in full swing, and we couldn’t be more thrilled. While it can be easy to rely on classic styles like riding boots and Dr. Martens, this footwear category is also a prime place for making a fresh statement: Think about the rise of motorcycle boots, for instance. A good boot trend balances a fun silhouette with timeless potential to embrace for seasons to come, and one such versatile style we have our eyes on right now is the effortlessly chic square-toe boots. It has a modern feel yet easily goes with any look, providing the perfect subtle wardrobe switch-up. Ahead, learn all about the square-toe boots trend, complete with options to shop for every price point and aesthetic.
About the Trend
Square-toe silhouettes have been one of the biggest fall shoe trends, popping up on everything from ballet flats to heels. The geometric style feels less expected in comparison to the pointed toes that had been at the forefront of trends in seasons past, it’s often as comfortable as it is stylish—so it’s no wonder that this shape has now taken over boots as we head into winter.
Given that the minimalist “old money” style continues to trend, it only seems right that this subtly sophisticated toe shape is having a moment. The luxe-looking style is an easy way to elevate any look, from a festive holiday dress to a casual winter sweater. In addition, more options in this silhouette are available than ever thanks to a slew of brands hopping on the trend, ranging from neutral everyday staples to statement-making details and hues.
Many brands, from Sam Edelman to Brother Vellies, have offered their takes on the trending style with classic ankle booties as well as tall, knee-high options that can take you from day to night. Keep reading to find 12 investment-worthy boots that will certainly become closet staples this winter.
Our Favorite Square-Toe Boots to Shop
Head-Turning Heel: Linea Paolo Saylor Square-Toe Boots
These sleek square-toe boots have an eye-catching, architectural stacked heel, making them truly one of a kind. They also feature a stylish front seam and a cushioned footbed to keep you comfortable whether you’re at the office or out for the night.
Sky-High Style: Brother Vellies Lauryn Square-Toe Boots
Brother Vellies never fails to be at the forefront of the hottest shoe trends, so it’s no surprise the brand put its own spin on the popular footwear style. These mid-calf caramel boots feature a square toe and a three-inch stacked wooden heel.
Best of Both Worlds: Charles & Keith Elongated Square-Toe Kitten-Heel Calf Boots
These Charles & Keith calf boots marry the luxe feel of a pointed-toe boot with the modernity of a square-toe design. The elongated toe box seamlessly leads into a tapered square silhouette. The kitten heel adds a slight lift to your look, helping you easily transition from day to night.
Chocolate Suede: Reformation Frederique Knee High Boot
You can never go wrong with a pair of classic knee-high boots, and this chocolate brown pair fits the bill perfectly. With a suede shaft that leads into a leather bottom, a zipped side, and a block heel, these will become your new go-to boots for fall and winter.
Sleek and Elevated: Vagabond Hedda Tall Boots
Tall, knee-high boots are a chic addition to any capsule wardrobe. This black leather pair from Vagabond pairs a square toe with a flared heel silhouette. Style them with a trending “mob wife” coat and a mini dress for any upcoming holiday soirées.
Square-Toe Siren: Sézane Axelle Ankle Square-Toe Boots
Embrace Parisian style with this pair of ankle boots from Sézane. The high-heeled boots are made of shiny patent leather (in an on-trend shade of cherry red, no less) and feature a wooden block heel. Style them with a mini skirt, tights, and a white button-down for a French girl-inspired winter look.
Ultramodern Vibes: Zou Xou Ola Glove Square-Toe Boots
Dare to make a statement in these suede boots from Zou Xou. The square-toe shoes have a playful pyramidal heel that comes in a little under two inches. Plus, you can shop them in this expensive-looking chocolate brown shade (which we deemed a winter neutral).
Everyday Ankle Bootie: Everlane The City Boot
These square-toe boots are a favorite at Byrdie and earned a spot as one of our best leather boots picks. The everyday style has a zip-up side and a pull tab, making it easy to put on and take off.
Stitched in Style: Maguire Prato Ballerina Boot
Sometimes, the littlest details can take a simple black boot to the next level, which is the case with this style from Maguire. Made with black pebbled leather, the shoes feature subtle yet attention-grabbing details, including white stitching and an on-trend square toe.
Stomping Season: Dr. Martens Maybole Square Toe Chelsea Boots
These Dr. Martens Chelsea boots get an upgrade with a square toe and a black and red gradient finish. Not only are these on trend, but shoppers say that they’re “super comfy.” The shoes also have an edgy structural heel with sharp corners, ensuring you’ll stand out as you stomp around town.
Winter Western: Franco Sarto Gracelyn Zip Boot
Add a bit of country to your winter wardrobe with this pair of square-toe boots. The leather shoes have subtle Western-inspired stitching and a small stacked chunky heel.
Subdued Sophistication: Sam Edelman Paige Bootie
These suede booties are a closet staple that will never go out of style. They come in luxe-looking colors, from chocolate brown to an almond shade. One Nordstrom shopper says they are “beyond comfortable,” while another reviewer wrote that they “love everything about these boots.”
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