Style Recipes: Jeans + Boots, 3 Ways

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For those of you looking at the new shapes of denim—wider legs, frayed edges and cropped hems—and wondering which boots to wear with ’em, we’ve got you. Or rather, our stylist Pippa does. Here, she breaks down the wardrobe recipes you need now. Get a leg up. A step in the right direction. Let’s get kicking. (You get the idea.)

Try: the Modern Cuff + Minimalist Boots

The ingredients:

Vintage-inspired jeans (preferably with a rip or two)

A streamlined ankle boot

How and why to do it, according to Pippa:

“This is all about the single tall cuff. This is a sidenote but it’s important: Cuffs and rolls are different. Rolling up and up can get bulky. A cuff is straight, cleaner and more grown-up. It also acts like an anchor and helps slouchier boyfriend fits hang nicely. Cuff the jeans before putting them on—it’s much easier to get the ideal shape when you’re not bent over! With your boots on, standing up, adjust the cuff so it hits the top of the boot. As for the boots: You can really wear any shape you want, but keep the style simple, without too many buckles or zippers. Dark colors balance a lighter denim wash, so I’m wearing our classic Billie Boot in blue suede.”

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Try: Cropped Jeans + Tall Boots

The ingredients:

A cropped-hem jean

Boots that hit above your ankle

How to do it, according to Pippa:

“Here’s the thing with a cropped fit: In the summer, it’s about exposing your ankles, but I like the surprise of wearing a crop and not showing any skin at all. Just wear a boot that hits a few inches above your ankle and meets the hem of your jeans. As it gets colder, this is functional too. I love mixing two elements that seem to be from different places, times or styles—what’s more fun to see than an unfinished hem right up next to a very polished boot? Try it.”

 

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Try: Classic Slim Jeans + Low-Cut Boots

The ingredients:

Skinny jeans (any color—we’re feeling true-blue indigo)

A boot that shows off your ankles (you’ll see why that matters in a minute)

How to do it, according to Pippa:

“When you hear ‘boot,’ you probably immediately imagine a shoe that covers your ankle or higher, but that’s not a requirement. Boots that hit below your ankle are some of the most versatile. The lower the boot, the more you see of the jean. The low heel is perfect for a day of errands that transitions right into dinner and maybe dancing. Because your shoes should never be calling the shots.”

Now that you’re ready to dress from the ground up, show us how you’re wearing your boots and shoes. You could win a $2,000 Madewell shopping spree, plus all the essentials for staying well heeled: two pairs of Madewell boots (your choice), a year of Spotify premium, headphones from Grado Labs, snacks from Baked and a Mizu water bottle.* Make sure to add #wellheeled #contest to your snaps so we see them.

Shop our Boot & Shoe Shop here and our jeans here.

*Open to legal residents of the 50 United States (D.C.), 18 years or older. Enter Contest by 11/14/16. For Official Rules, including prize descriptions, visit www.madewell.com/wellheeledrules. Void where prohibited.

Photography by Jennifer Trahan.