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As of late, practically every time we’ve spotted Kendall Jenner, she’s been wearing super-sharp, point-toe boots or heels. As such, the ‘90s silhouette has hit its stride in 2022, quickly becoming one of the year’s most sought-after styles following a long period of round- and square-toe supremacy. There’s only one problem. After spending so much time away from our wardrobes, we’re all a bit rusty on what to actually wear with all our new pointy footwear. That’s where Jenner comes in.

From pairing the style with tights and underwear (no pants in sight) to combining them with leather trenches, the supermodel’s street style has become a how-to of sorts, demonstrating every cool way to wear point-toe shoes. And her latest look is no exception. Spotted leaving a late-night dinner at Giorgio Baldi in Santa Monica, Jenner wore an all-pistachio outfit, including a deep-V sweater, matching suede pants, and her regular point-toe boots. Particularly note-worthy were her bottoms, the shape of which appears to be the perfect match for her go-to shoes. Low-rise with a bootcut shape, they fall perfectly over the toe of her shoes, highlighting the shoe trend everyone either wants to be or is wearing right now. Shop every pointy shoe’s perfect match below. 

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