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 ($100, $50) that capture the iconic shape—without looking Lord Farquaadian.
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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Published Feb 7, 2024
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Dasha Burobina for PureWow
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Why You Should Trust Us
PureWow's editors and writers have spent more than a decade shopping online, digging through sales and putting our home goods, beauty finds, wellness picks and more through the wringer—all to help you determine which are actually worth your hard-earned cash. From our PureWow100 series (where we rank items on a 100-point scale) to our painstakingly curated lists of fashion, beauty, cooking, home and family picks, you can trust that our recommendations have been thoroughly vetted for function, aesthetics and innovation. Whether you're looking for travel-size hair dryers you can take on-the-go or women’s walking shoes that won’t hurt your feet, we’ve got you covered.