Square-Toe Shoes Are Here to Stay, and Here are 21 of Our Favorite Pairs
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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
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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1. Vivaia Square-Toe Heels
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.
2. The Drop Avery Sandals
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.
3. Sam Edelman Terra Pumps
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.
4. Stuart Weitzman Cayman Sandals
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.
5. Nordstrom Rack Square-Toe Flats
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.
6. Vicenza Bow Flats
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.
7. Vince Camuto Reselm Sandals
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.
8. Tory Burch Patos Sandals
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.”
9. Dolce Vita Reyes Flats
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.”
10. Rothy's The Square Flats
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.
11. Steve Madden Isa Wedges
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."
12. Vince Venice Flats
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.
13. Reformation Louie Stretch Booties
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.
14. Lulus Arabelle Boots
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.”
15. Marc Fisher Mayson Sandals
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.
16. Bibi Lou Valencia Heels
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.”
17. Vionic Orinda Flats
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.
18. Soludos The Original Dali Espadrilles
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.
19. Loeffler Randall Daphne Slides
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.
20. Marc Jacobs J Sandals
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.
21. Covet Shoes Wyatt Heels
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.
Vivaia vs. Rothy’s: Which Comfy, Cute and Sustainable Ballet Flats Reign Supreme?
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.
