The One Rule For Pairing Ankle Boots With Wide Leg Jeans

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You finally set aside your skinny jeans to try out a new denim style this fall? Bravo. We think you’re going to like the freedom that comes with wide-leg blues (after all, they’re almost as comfortable as sweatpants).

But, as you’ll soon learn, pairing these guys with any old ankle boot doesn’t quite look right. In fact, there’s just one shoe style (ankle boot or otherwise) you should be wearing with your fresh new jeans: a pointy toe.

Here’s why: A skinny jean draws the eye towards the ankle, the slimmest part of the leg. This offers an instantly elongating effect, no matter your footwear—combat boot, sneaker, ballet flat, you name it. The pants also do a stellar job of showing off every inch of an ankle bootie, especially if you cuff your jeans up an inch or two.

Wide-leg denim, on the other hand, isn’t as easy to wear with any old shoe—and a rounded toe (yes even on a sneaker) can actually make your legs look shorter than they are. As for a square toe? You’ll end up looking like you just stepped off the set of Friends in 1997.

A pointy-toe boot, however, gives your legs a little vertical boost. It’s the extra length and the sharp, clean-cut that makes this combo so universally flattering. Not to mention, it feels undeniably modern.

So, who’s with us for wearing pointy ankle boots and wide denim? Below, shop our fave combos.

Fall’s Biggest Denim Trend *Might* Get You to Ditch Your Sweatpants (at Least for a Day)

Wide Leg Jeans & Ankle Booties We Love

Citizens of Humanity Flavie Trouser Jeans

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Marc Fisher LTD Ulani Pointy Toe Bootie

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Levi's WellThread Ribcage Ankle Wide Leg Jeans

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CC Corso Como Daeyna Bootie

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Apiece Apart Merida Jean

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Stuart Weitzman Melena Leather Ankle Boots

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