The perfect heel is short, stacked, sturdy, and therefore actually walkable all on top of being mysteriously more lengthening than a Pilates machine. It's part of what makes the Beatle boot so great for fall. And there’s just something about September that makes me want to run around New York in ‘60s-feeling sweaters, miniskirts, and ankle boots like an aspiring Louis Vuitton mannequin. Care to join?
Loeffler Randall Felix Stacked Boot: Before you rule out an exotic print, consider a week's worth of standard outfits. Chances are at least half of them would look amazing with these guys.
Zara Block Heel Leather Boot: This low, block-heeled take comes with plenty of visual interest, including—but not limited to—a pony hair exterior and zippers worthy of display.
Alexander Wang Sunniva Degradé Boot: A modified Cuban heel adds appeal to otherwise straightforward shoes—that, and a black-and-blue dye job.
All Saints Delilah Boot : Taller and of the Chelsea variety, these will hug your ankles with stretchy elastic panels. Like broken-in riding boots, but shortened.
Topshop Ashley Pointed Ankle Boot: Pointed, patent, and satisfyingly witchy, these booties will ensure at least one compliment before your morning coffee run—quality results guaranteed.
—Claire Knebl