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Square-Toe Shoes Are Here to Stay, and Here are 21 of Our Favorite Pairs

This ‘90’s trend is *finally* back

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best square toe shoes for women collage
Dasha Burobina for PureWow

The square toe-shoe was a proverbial statement of the ‘90s, and as Justin Timberlake once said, “what goes around comes around,” especially in fashion. Sure, the style has reportedly been around since medieval times, bobbing in and out of fashion for both women's and menswear over the centuries, but most of us associate them as a ‘90s style staple. And now, yet again, the look is at the top of this year’s trends, so we’ve found 21 pairs, from stylish sandals (was $100, now $50) to walkable heels ($139) that capture the iconic shape—without looking Lord Farquaadian.

The Top Five Square-Toe Shoes for Women at a Glance

1

Most Comfortable

Vivaia Square-Toe Heels

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2

Best on Amazon

The Drop Avery Sandals

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3

Best Metallic

Sam Edelman Terra Pumps

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4

Most Splurge-Worthy

Stuart Weitzman Cayman Sandals

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5

Most Affordable

Nordstrom Rack Square-Toe Flats

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How We Chose the Best Square-Toe Shoes for Women

When selecting the best square-toe shoes for you to shop, we vetted customer reviews to find styles buyers were happy with even after wearing them for long periods at a time, polled our editors for their tried-and-true recommendations and looked at some of the top-rated products across trusted retailers like Nordstrom, Bloomingdale’s and more.

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Most Comfortable

1. Vivaia Square-Toe Heels

What We Like

  • pressure-relieving cushioned bottom
  • walkable block heel

What We Don't Like

  • minimal arch support

Vivaia

Vivaia’s shoes are beloved for their ultra-comfortable feel thanks to the padded pressure-relief insole that provides support across the foot. Assistant Commerce Editor Natalie LaBarbera loves the knit outer fabric, too, she explains: “These block heels are the perfect shoe that really can be worn anywhere. The ribbed knit fabric has such a stylish look and is flexible enough that they don’t need to be broken in. I love the padded footbed as well, but do wish they had just a touch more arch support.” The shoes also have a padded heel patch at the back to prevent rubbing.

Fast Facts

  • Material: knit upper, natural Artemisia Argy and PU foam insole
  • Heel Height: 1.77 inches

Best on Amazon

2. The Drop Avery Sandals

What We Like

  • budget-friendly
  • comfortable

What We Don't Like

  • may not hold up over time

The Drop

Because they can be dressed up or dressed down, these sleek sandals are the perfect finishing touch to any outfit. They can slip on and off with ease, and their wide heels make them easy to walk in, especially if you’re trotting around the city. They also come in a whopping 37 colors and designs, including croc patterns and styles with edgy studded straps.

Fast Facts

  • Material: polyurethane
  • Heel Height: unlisted

Best Metallic

3. Sam Edelman Terra Pumps

What We Like

  • trendy style
  • block heel

What We Don't Like

  • may not stay comfortable wearing for long periods at a time

Sam Edelman

Metallic shoes and bags are trending in a big way recently, and this pair feels like the perfect all-season pick to easily bring a bit of that sparkle to your everyday outfits. We love this pair from Sam Edelman that has an elegant slingback style and not-too-high block heel. Shoppers say they’re super versatile and fit true to size, but note that they start losing a bit of their comfort if worn for a long amount of time.

Fast Facts

  • Material: leather upper, synthetic lining
  • Heel Height: 2 inches

Most Splurge-Worthy

4. Stuart Weitzman Cayman Sandals

What We Like

  • linen fabric
  • low block heel

What We Don't Like

  • spot clean only

Stuart Weitzman

We can’t get over the classically chic, timeless style of these slide sandals from Stuart Weitzman. The sandals are crafted from a linen fabric that’s perfect for the (hopefully) approaching warmer weather and will go with just about anything in your closet. They also have a low block heel, so you can wear them comfortably all day long without wanting to rush home to change into something flat.

Fast Facts

  • Material: linen, cotton, polyurethane, leather
  • Heel Height: 1.38 inches

Most Affordable

5. Nordstrom Rack Square-Toe Flats

What We Like

  • versatile
  • budget-friendly

What We Don't Like

  • no arch support

Nordstrom Rack

If you’re looking for something that will totally fit your budget while still being ultra-versatile, you’re in luck. This pair of flats from Nordstrom Rack has it all. They’re designed with a sleek faux leather fabric and simple ballet design that can just as easily work for a day at the office as it can for more formal events or even grabbing coffee on the weekends.

Fast Facts

  • Material: synthetic leather
  • Heel Height: none

Best Trendy

6. Vicenza Bow Flats

What We Like

  • trendy style
  • comfortable

What We Don't Like

  • no arch support

Vicenza

The bow trend is showing no signs of slowing down, and these gorgeous flats will have you channeling your inner Carrie Bradshaw in no time. The flats are made of soft leather, so you can easily adjust the tie at the top, and reviewers rave that they “don’t disappoint” and have the “most comfy and elegant fit,” but note that there isn’t any arch support.

Fast Facts

  • Material: leather
  • Heel Height: none

Best Black Square-Toe Shoes

7. Vince Camuto Reselm Sandals

What We Like

  • padded footbed
  • slip-on

What We Don't Like

  • few color choices

Vince Camuto

These bad boys from Vince Camuto come with flared heels that are just over three inches so you can strut comfortably (and with less fear of twisting an ankle as you dash from one place to another). The best part? We’re torn between the subtle, quilted detailing that gives them that extra oomph and the fact that they're designed with a padded footbed for extra cushioning.

Fast Facts

  • Material: synthetic sole, unlisted upper
  • Heel Height: unlisted

Best Slides

8. Tory Burch Patos Sandals

What We Like

  • low heel
  • cushioned insole

What We Don't Like

  • few color choices
  • pricey

Tory Burch

Slide right into these stunning leather sandals adorned with a gold disc, inspired by ‘60s glamour, that instantly elevates their look. The shoes have a slight heel for just the right amount of lift and are designed with a cushioned insole to keep your feet from hurting, even if you’re on your feet all night. “These shoes are chic in an elevated sort of way with lovely details, like the gold disc and the gold accent on the heel,” one reviewer says. “These details also lend themselves well to being dressed either up or down. I only wish I had purchased them in both colors; would highly recommend.”

Fast Facts

  • Material: leather
  • Heel Height: .98 inches

Best Mary Janes

9. Dolce Vita Reyes Flats

What We Like

  • versatile
  • partial recycled materials

What We Don't Like

  • no arch support

Dolce Vita

It doesn’t get more classic than a good pair of Mary Janes, and we just know you’ll find yourself wearing this pair for years to come. The Reyes flats from Dolce Vita are partially made with recycled materials, too, so they’re an eco-friendlier choice, but it’s the fit that has reviewers raving. Take this assessment, for example: “They are true to size and absolutely adorable. They are also very comfortable [and] are great way for me to dress up my outfit, but still be comfortable [while] chasing my kids around.”

Fast Facts

  • Material: leather upper, recycled synthetic outsole, textile lining
  • Heel Height: none

Best Washable

10. Rothy's The Square Flats

What We Like

  • machine washable
  • flexible fabric

What We Don't Like

  • air dry only

Rothy's

We always appreciate being able to toss our stuff in the washer when it inevitably gets a stain or two, which is why we adore these flats from Rothy's. Thanks to their soft knit fabric, these babies can go right in the wash just like the rest of your laundry (just be sure to separate the insoles first to get the best cleaning), keeping them looking fresh every time you wear them.

Fast Facts

  • Material: signature knit made from recycled bottles
  • Heel Height: none

Best Wedges

11. Steve Madden Isa Wedges

What We Like

  • slip-on
  • unique style

What We Don't Like

  • reviewers vary on their comfort

Steve Madden

Show off your pedicure when spring arrives with these lovely sandals. We’re sure you’ll love the clear, two-inch wedge heels and the sturdy, thick straps. The bold green color is right on trend, too, and reviewers say they're versatile and easy to walk in: "[These go] with absolutely anything and everything...The clear wedge makes it even more versatile, [and they're] super easy and comfortable to walk in all day or night."

Fast Facts

  • Material: leather and synthetic
  • Heel Height: unlisted

Best Slingbacks

12. Vince Venice Flats

What We Like

  • true to size
  • soft feel

What We Don't Like

  • pricey
  • may run large

Vince

Designed with a ruched front and elegant slingback strap to keep them in place, these shoes are simultaneously on-trend and a classic you’ll want to keep in your shoe collection forever. They come in five colors—from neutrals to a showstopping crimson—and the subtle heel makes them wearable for any occasion (especially ones that require you to be on your feet a lot). Shoppers note they feel super soft and high-quality, but also say they may run a bit large.

Fast Facts

  • Material: leather
  • Heel Height: .62 inches

Best Booties

13. Reformation Louie Stretch Booties

What We Like

  • side zipper
  • true to size
  • stretchy material

What We Don't Like

  • pricey

Reformation

These booties are designed with a mid-height block heel, convenient side zipper and soft feel. Add in the *stretchy* leather fabric and we’re sold. According to the brand, they also run true to size and have a “glove-like” fit, and since we can totally see ourselves wearing these on repeat, we think they’re definitely worth the investment.

Fast Facts

  • Material: nappa leather
  • Heel Height: 1.97 inches

Best Tall Boots

14. Lulus Arabelle Boots

What We Like

  • budget-friendly
  • block heel

What We Don't Like

  • few color choices

Lulus

If you’ve been on the hunt for a taller square-toe boot, look no further than this Arabelle pair from Lulus. They’re made from a soft, faux-suede fabric and have a full zipper up the inner side so there will be no struggling to tug them on and off as you’re getting ready. They also have a 3.5-inch block heel that reviewers confirm is easy to walk in: “These boots run true to size [and are] easy to walk in and [are] comfortable. [They’re also] very chic and on-trend with the square toe.”

Fast Facts

  • Material: faux suede
  • Heel Height: 3.25 inches

Best Sandals

15. Marc Fisher Mayson Sandals

What We Like

  • slip-on
  • soft faux leather

What We Don't Like

  • little arch support

Marc Fisher

Talk about stylish. We adore the unique knotted design of these sandals, which look high end but don’t put a big hit on your budget. They’re also made from soft faux leather, making them pliable—less chance of getting blisters as the fabric brushes against your skin—and the minimal heel won’t leave your feet aching after a day’s wear.

Fast Facts

  • Material: faux leather
  • Heel Height: unlisted

Best Heels

16. Bibi Lou Valencia Heels

What We Like

  • block heel
  • classic style

What We Don't Like

  • may need broken in a bit

Bibi Lou

Instantly take your daily looks up a notch with these chic heels from Bibi Lou. The leather shoes are adorned with a fabulous gold buckle and feature a 2.75-inch block heel and shoppers love their timeless look. One happy one writes: “This shoe is a true classic! I love the timeless chic look and the colors are simply beautiful. The fit is perfect and very comfy. Perfect for a long day at the office.”

Fast Facts

  • Material: leather
  • Heel Height: 2.75 inches

Best Flats

17. Vionic Orinda Flats

What We Like

  • Vio Motion comfort technology
  • arch support

What We Don't Like

  • may run large

Vionic

Outfitted with the brand’s Vio Motion comfort technology that’s intended to keep your feet feeling great all day long, these Orinda flats from Vionic are the staple your wardrobe needs. The insoles are also removable in case you want to add custom orthotics. Just note some reviewers say they ran a bit large, so you may want to consider going down a half-size.

Fast Facts

  • Material: leather upper, EVA footbed
  • Heel Height: .5 inches

Best Espadrilles

18. Soludos The Original Dali Espadrilles

What We Like

  • organic cotton material
  • breathable

What We Don't Like

  • no arch support

Soludos

Reviewers say they want to wear these shoes every day, and we can’t blame them. These classic espadrilles are made from a breathable organic cotton upper material, with an authentic, biodegradable jute base and cotton lining. They’re available in tons of different colors, too, so you’re sure to find a shade for any outfit, and they have padding at the heel to keep them from slipping off.

Fast Facts

  • Material: cotton, jute, microsuede, linen
  • Heel Height: none

Best for Vacation

19. Loeffler Randall Daphne Slides

What We Like

  • vegan-friendly
  • padded footbed

What We Don't Like

  • runs small

Loeffler Randall

A padded footbed, vegan-friendly materials *and* an adorable design—what more could we ask for in a sandal? These Daphne slides from Loeffler Randall are totally vacay-worthy, too, thanks to their natural straw fabric that’s practically begging to be worn to brunch under the palms. The brand does note that this style tends to run small and suggests sizing up a half size for narrow feet and a full size for wider feet.

Fast Facts

  • Material: raffia and faux leather
  • Heel Height: unlisted

Best Colorful

20. Marc Jacobs J Sandals

What We Like

  • bold color
  • slip-on

What We Don't Like

  • no arch support

Marc Jacobs

We *still* can’t get enough of Barbie pink around here, and these slides are the perfect way to bring a pop of the bold hue to your looks. Thanks to the slip-on style, these sandals are easy to just throw on and go when you’re late for coffee with your besties and want to feel stylish without having to put in a ton of effort.

Fast Facts

  • Material: leather upper, synthetic sole
  • Heel Height: .15 inches

Best Vegan

21. Covet Shoes Wyatt Heels

What We Like

  • vegan leather
  • weather-resistant

What We Don't Like

  • pricey shipping

Covet Shoes

We didn’t think a 3.5-inch heel could look cozy, until we spied this pillowy pair. These vegan leather heels are made with a padded sole and stylish puffy interlaced top, plus they’re weather-resistant, so you don’t have to worry about them getting ruined if you’re caught in unexpected rain. Despite its height, the heel should feel supportive, too, thanks to its sturdy block construction.

Fast Facts

  • Material: vegan leather
  • Heel Height: 3.5 inches

natalie bio photo e1692204716113

Assistant Commerce Editor

Natalie LaBarbera is PureWow's assistant commerce editor. She writes about all things shopping, including fashion, beauty, travel, wellness and more, searching for the best...

purewow author

Freelance Writer

Jackie Manno is an avid shopper, and is always staying up to date on the latest products, especially in beauty and fashion, to help empower readers, make them feel beautiful and...

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