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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.

On Kendall Jenner: Bottega Veneta shoes;Le Chic Radical earrings

Low rise, big flare is the pant combo of the season.

These are selling like crazy.

I haven’t stopped thinking about these since they dropped on Reformation. Can you blame me?

Currently obsessing over cords for fall.

The ’70s vibes are strong and I’m into it.

Cuteness overload.

These suede pants are calling your name (and mine).


The perfect holiday-season pant—found.

The zipper closure feels so 2002 and I can’t get enough of it.

The easiest throw-on-and-go pants.

I’ll never pass up an opportunity to buy leather pants.

For work and play.

These are number one on my buy list. 

These will go so much use during the holiday-party circuit this year. 

If you already own black, point-toe boots, make these your next purchase. 

This price is simply too good to pass up.

I adore a winter-white moment. 

These are in my Nordstrom cart as we speak.

Excuse my drooling.

A bold choice that will absolutely pay off.

Someone pull me away—I can’t stop looking at these. 

I mean, duh. 

Next: Kendall Jenner Wore Underwear With Nothing But Tights for a Busy Day Out in L.A.

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