Pointy-Toed Shoes, From Vintage Finds to Brand New Styles

From the classic stiletto to the kitten heel to the mod flat, pointy-toed shoes are the sharp way to revive your wardrobe fast

Making Good Points, Circa 1955; Photo Courtesy of Getty Images

Making Good Points, Circa 1955; Photo by Getty Images

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.

The Spectator

White and Navy Spectator Pumps, $30, Stella Luna, Toronto; Photo by Daniel Harrison

Photo by Daniel Harrison

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.

3-Pointy-Toe-PumpMiu Miu, $750, Spade New York, $335,

The Standby

Photo by Daniel Harrison

Photo by Daniel Harrison

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.

6-Pointy-Toe-PumpL.A.M.B, $300, Laurent, $760,

The Coquette

Photo by Daniel Harrison

Photo by Daniel Harrison

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.

9-Pointy-Toe-PumpDries Van Noten, $815, Gravity Pope. 10-Pointy-Toe-PumpMarc Jacobs, $655, (212) 343-1490.

The Preppy Mod

Photo by Daniel Harrison

Photo by Daniel Harrison

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.

12-Pointy-Toe-PumpAsos, $60,
13-Pointy-Toe-PumpZara, $100,