My Square-Toe Boots Are Killing Me—What Ones Should I Wear Now?

I’ve been wearing square-toe boots for about three years now, every fall and winter, specifically ones by the Ukrainian label Bevza. The designer, Svitlana Bevza, molded them off of a ’90s shape with a 90-degree angle—delicious. At the time, square-toe boots were becoming a phenomenon on the runways of Balenciaga and on the Instagram of the It-girl label By Far. A square toe is the pinnacle of bad-meets-good taste, and in the right context it becomes sleek. (No dull edges here.) But I’m all out of options, as my pair are falling apart and Bevza won’t make them for a while. In my grieving process, I’ve been exploring other types and have fallen in love with severe, razor-sharp pointy-toe shoes. 

In one article, I praise those delicious dagger heels, and name-check the reality television patron saints of pointed pumps. Though that footwear is designated for 9-to-5 business and maybe a date night, pointed-toe boots are another story. They are crafted for the wear and tear of standard boots, but still have a catlike prowess of a sleek and sharp pump. This isn’t the same for round- or blunt-toe boots, which feel more appropriate for daytime dawdles, maybe horseback riding. A sharp toe comes with a longstanding mission. For this story, I was browsing the archives of Vogue looking for images of pointed-toe boots, and behold, I found a page from September 1997, edited by Candy Pratts Price, that featured five mean-looking, calf-skimming boots from Manolo Blahnik, Marc Jacobs, and more. The writer Sarah Van Sicklen described them as: “After sensible shoes—think round, think clunky—it’s high time designers upped the danger quotient with pointed-toe, ice pick heels, and a heady dose of attitude.” 

That “danger” factor is all too real. I think about the first Charlie’s Angels, and its trifecta of babes: Cameron Diaz, Drew Barrymore, and Lucy Liu, who all kick ass in crop tops and pointy-toe boots. There is an epic moment when Diaz, in an off-the-shoulder red top, slams a goatee’d foe in the throat with the sole of her horrifyingly knife-style stiletto boots. The same goes for Charlize Theron in Atomic Blonde, a film that is packed with punches and machete-edged boots. 

The time seems right for footwear to have a point: Balenciaga has churned out some sinisterly sharp cuissardes from the fall 2020 collection, as has Louis Vuitton and Marc Jacobs. Fashion aside, I love the idea of a woman in power who can pirouette-kick a pathetic guy into oblivion. It’s satisfying. While I won’t be doing that (at least, not often), I also don’t want to be traipsing around all cold weather long in boots with buffed edges. As a woman on a mission, I want my footwear to mean something—and to look a little mean, too.