If you pay attention, you’ll notice that fashion tends to move in a 20-year cycle; what was trendy two decades ago will inevitably make its comeback in the present. And since it’s 2020, our point of reference is, for better or worse, the messy decade of the 2000s.

You can already see the sartorial trappings of the era all around you, whether through glitzy hair clips, Fendi Baguette bags or even the once uncool cargo pants. Another case in point: the square toe shoe, whose relentless staying power amongst the fashion crowd is credited, mostly, to Daniel Lee’s Bottega Veneta.

Rihanna Porcelain Ball 2019
Rihanna in Fenty thong sandals (Photo credit: Getty Images)

The brand’s takes on the square toe sandal, one of which was the most searched shoe of 2019, have spawned countless variations from several other brands including Balenciaga, Jacquemus and Saint Laurent. The trend is no longer restricted to the strappy heel, either. There are square toe mules, square toe boots and even square toe flats to work into your wardrobe.

So, if you haven’t already, dip your toe into 2020’s biggest shoe trend with all its stylish manifestations below.

1
Bottega Veneta padded sandals

No shopping list for square toe shoes would ever be complete without a pair from Bottega Veneta. The Italian brand has become a street style favourite for its strappy sandals and mesh pumps in the distinctive shape, but its newest quilted mules are the ones set to dominate 2020. Featuring a hand-stitched strap that nods to Bottega Veneta’s famous intrecciato weave, this pair comes in bright, powder blue — a colour perfectly aligned with Spring/Summer 2020’s trends.

S$1,250, Bottega Veneta

 

2
Saint Laurent Tribute mules in tortoiseshell patent leather

Saint Laurent proves that slippers can be stylish, too. These slip-ons are elevated with their sleek patent leather finish and geometric shape. With no heels to speak of, they’re also pretty comfy and make the perfect summer holiday staple piece. They’ll go with pretty much any outfit thanks to their colour, but the shoes are best paired with a laid-back ensemble like a T-shirt and a pair of high-rise slim jeans.

S$1,040, Saint Laurent

3
Jil Sander whipstitched square-toe leather ballet flats

It makes sense that ballet flats now have their pointed tips cut off, too. They were, after all, inspired by the boxy pointe shoes in which ballerinas danced on the tip of their toes. But enough toe talk. This cream Jil Sander pair will give you an air of elegance, ballet dancer or not. It also has some unique details, such as a metal ankle cuff and whipstitching all along the shoe. Wear these on a stroll in a park, coupled with a breezy summer dress.

S1,070, Matches Fashion

4
Jacquemus Manosque leather sandals

Like Daniel Lee, Simon Porte Jacquemus has a knack for designing accessories that women are guaranteed to fall in love with. Take these Manosque shoes, for example. Jacquemus’s offering stands out from all other strappy square-toed sandals with its round, sculptural heel, giving it a touch of French Riviera glamour.

S$527.31, Net-a-Porter 

5
By Far Diana slingback in tan croco embossed leather

Another notable purveyor of square toe footwear is By Far. The Kendall Jenner-approved accessories label takes inspiration from pop culture and TV shows like Sex and the City; inevitably, their selection of mules, slingbacks and sandals look like they came straight out of Carrie Bradshaw’s closet. Their Diana slingbacks, inspired by the ones worn by the late Princess Diana, are great if you’re not quite ready to go full square toe — or if you like a little bling, courtesy of an embellished kitten heel.

S$‌705, By Far

6
Wandler Isa two-tone leather mules

Dutch label Wandler has long been a cult favourite for its handbags, but it has also translated the cool-girl appeal of its designs into its footwear line. Their Isa mules, in particular, point to the brand’s ability to tap into the trends of the moment. Aside from the square toe sole and its matching vamp, the shoe comes in an array of vibrant colours fit for the season. With its electrifying blue hues, this pair is an enticing option for your next party get-up.

S$352.57, Net-a-Porter

7
Staud Billie printed canvas wedge sandals

If you really want to throw it back to Y2k fashion, get these Staud wedges. The clunky shoes almost resemble the ones sported by Paris Hilton in her The Simple Life days, except that the Toile de Jouy pattern refines the open toe pair and gives it a summery vibe.

S$231.32, Net-a-Porter

8
Balenciaga double square BB zipped booties

The square toe isn’t just reserved for flirty summer sandals. Balenciaga shows us that the unconventional sole works just as well in tougher styles such as boots. This sculptural pair gives off major Matrix vibes with its perfectly square heel and smooth black leather façade. And just like Neo, you’d be way ahead of the curve wearing them.

S$1,690, Balenciaga

9
Ganni crocodile-effect leather knee-high boots

Knee-high boots are another reigning trend this season, having dominated several runways from Celine to Givenchy. Why not kill two trends with one pair of shoes? These Ganni leather boots will take your look to greater heights with its croc-effect texture and chunky Cuban heels. The message is clear: you’re not here to play.

S$830, Matches Fashion

Pameyla Cambe
Senior Writer
Pameyla Cambe is a fashion and jewellery writer who believes that style and substance shouldn't be mutually exclusive. She makes sense of the world through Gothic novels, horror films and music. Lots of music.