Photography by Michele Equitz

Vans flannel (similar) | Aritzia jacket (similar) | Mott & Bow denim | Thrifted handbag | Boots c/o Frye + Co

Not that it matters, but I’ve made my 30th birthday a deadline for the time by which I should be able to walk in heels. I’ve avoided them my whole life—not because I didn’t like how I looked, but because I felt like a baby giraffe every time I tried to take a step. I’m kind of tired of turning down a dreamy pair of shoes just because they have a heel. I’ll never be a four-inch stiletto person (okay, I shouldn’t say never—my latest pick-up is a pair of 3.5” vintage Jimmy Choos), but I have noticed a huge difference in just committing to the shoe and practicing for a few hours a day.

It’s a big help when it’s a pair of boots you can lace up tightly with a chunky heel, like these from Frye’s new line Frye + Co. I’ve always wanted a pair of boots like this—they look a little outdoorsy, but made for the city. I always love a conundrum.