Even for those of us whose interest in footwear begins and ends with the latest flash sale, the history of the pointy-toed shoe is fascinating. From the Crackowes of the late 1400s to the Elizabethan courts, long, needle-like poulaines signified nobility—by law, only royalty could have the points extend more than one foot’s length beyond their toes. By the mid–20th century, pointy-toed spikes and proto-mod low heels had been embraced by Everywoman for work and play. Marc Jacobs, Louis Vuitton, Miu Miu and Christian Dior brought us back to super-pointy this spring, invoking both midcentury points and the 1990s take on the same trend. It’s all such a mash these days! But that’s great news: you can sleuth out vintage finds from either era, or choose from a trove of new designs—and all of them point in the right direction.
Easy, breezy, and a touch sportif: a classic white-and-navy spectator pump hits just the right note for summer. White and navy spectator pumps, $30, Stella Luna, Toronto.
The elongated toe cap, elegant duotone and spike black heel of a 90’s-era Chanel pump is timeless—but never boring. Beige and black pump, $495, I Miss You Vintage, Toronto.
This late-’50s kitten heel charms with its walkability and cut-out vamp detailing that echoes the cut-out dress. Black with front cut-outs, $40, Mintage, Vancouver.
Dries Van Noten, $815, Gravity Pope. Marc Jacobs, $655, (212) 343-1490.
The Preppy Mod
The minty pastel hue of a low-heeled pump with a loafer front is sweet without being cloying. Mint green with loafer front detail, $40, Mintage, Vancouver.