The Square-Toe Boots Trend Is Back — Here's How To Wear It

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Instagram has a way of making certain items feel entirely irresistible. What typically starts as a runway trend is quickly adapted for retail and subsequently translated to your social media feed where, seemingly all of a sudden, fashion influencers are all wearing the same must-have item or trend (and wearing it very well). Right now, the square-toe boot trend is a major Instagram favorite from sharply angled tips to slightly squared toes — a simple update to your wardrobe that’s totally worth testing this winter.

Unsurprisingly, square-toe boots are a ‘90s resurgence and have the ability to subtly change the feel of an outfit whether it’s casual or polished. For the umpteenth time in a row, a simple sweater, jeans, and ankle boots might feel uninspired. But with the punctuation of a square-toe boot, said basics are instantly enlivened for a right-now feel with minimal effort. Whether you keep it simple in a black ankle boot, test the textured waters of croc-effect and snakeskin prints, or go for a Victorian-inspired lace-up style, the angular effect somehow makes casual outfits feel sharper and dressier looks feel cooler— especially if you go for a bold color or print.

"I’m loving that the ‘90s square boot has been updated in mixed materials and such wearable colorways," says Shopbop’s fashion director, Caroline Maguire who finds western-inspired styles and sock-style ankle boots to be the most modern. "I would style these with a classic cropped trouser and steer away from wearing them with a dress to avoid looking too ‘90s."

While fashion risk-takers will be all about western-inspired styles (a look that was heavily championed by Calvin Klein on the runway and favorited by cool girls everywhere), sock-style ankle boots — in a neutral color like black, brown, ivory, or tan — are an easier foray into the trend and can be tucked into jeans or worn with tights under dresses and skirts.

"This season’s [square-toe] boot is all in the details making it a very versatile styling option," says Erica Russo, Bloomingdale’s vice president and fashion director for accessories and beauty. "From printed python to white leather or a studded harness, I love that this detail can read a little edgy or western and give your look an instant update."

Russo is also in favor of an easy outfit formula that doesn’t feel like a too-literal throwback, especially in combination with bolder boot styles. "Keep your look sleek and no fuss with cropped denim to really highlight the whole boot. You can also pair the boots back to a flowing midi dress to soften the silhouette."

However you choose to rock the square-toe boot trend this winter, ahead shop 27 favorites with influencer inspiration for how to style.

Naomi Black Silk

$492.61

by FAR

Heel Leather Ankle Boot

$149.99

$74.99

Mango

Kaya Booties

$625

Brother Vellies

Chelsea Sock-Style Ankle Boots With Studs

$0

$59.90

Zara

Low Texas Boots

$540

Ganni

Dolce Vita

$200

$140

Isara Leather Harness Block Heel Booties

For low-key impact, a colored pair of square-toe boots will pop against everyday denim, as proven by Alyssa Coscarelli. Punchy details like lace-up shapes, patent leather, and snakeskin will you earn you extra style points and are a fun alternative to neutral tones.

Mox Lace-Up Patent Boot

$249

Intentionally Blank

Crawford Square Toe Patent Leather Mid-Heel Booties

$690

$345

Creatures of Comfort

Square Toe Boots

$500

$354

Dorateymur

Lune Patent Tortoise Boot

$789

Maryam Nassir Zadeh

The Boo Ankle Boot

$700

$420

Jospeh

Square Toe Lace Up Boots

$611

Marques' Almeida

A minimal boot is versatile whether you wear with a feminine dress or vintage jeans. You'll get the most mileage out of wear-with-everything shades like tan and black and as Monikh Dale proves, white and ivory hues deliver the sleekest, right-now result.

Ellis Booties

$595

Rag & Bone

Trish 45 Suede Ankle Boots

$995

Gianvito Rossi

Lazaro in Cuero Leather

$375

Loq

Mirror Heel Boot

$1,590

Salvatore Ferragamo

Hendrik High Ankle Cuff Boots

$170

Topshop

Croc-effect and snakeskin boots are a luxe upgrade from neutrals (and both Insta-worthy crazes that seemingly won't quit), and the epitome of '90s-chic in a square-toe silhouette. Appearing effortless with high-waist jeans (as demoed by Sabina Socol), they're perfectly polished with workwear staples for a smarter vibe.

Boots Lucky Brown

$255

$205

Sabina Socol & Jonak

Salsa Croc-Effect Vegan Leather Ankle Boots

$470

Nanushka

Flat Ankle Boot

$750

$375

Rosetta Getty

Square-Toe Snakeskin Ankle Boots

$450

Barneys New York

Charm Angled Heel Booties

$525

$367.50

Freda Salvador

If you regularly rotate between T-shirts and sweaters with jeans, simple square-toe boots with an unexpected feature like a cool color, high-shine finish, or understated color-blocking effortlessly hits on the trend. Ali Tate's combination of a black top, leopard jacket, and raw-hem jeans is exemplary.

The Day Boot

$225

Everlane

RJ4 SH039 Square Ribbon Half Boots

$428

Reike Nen

Yy Boots Vol 3 -Ash Grey Camel Brown

$328

YY by Yuul Yie

Clara Square Toe Knee Boots

$135

$81

ASOS DESIGN

Square Toe Ankle Boots

$941

$565

Loewe