How to Wear Ankle Boots and Jeans

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Different Ways to Wear the Trend

Street style jeans and ankle boots
Wear attention getting ankle boots with skinny jeans. Christian Vierig/Getty Images

Ankle boots and jeans are a match made in heaven, as far as I'm concerned. While this fashion combination is trending like crazy, that doesn't mean it comes without its challenges. Worn the wrong way, you can end up looking dated, or just weird in shorter boots and jeans. That's why I've put together this go-to guide to how to always look fashionable in jeans and ankle boots, whether you're a skinny jeans type of gal, or are more partial to slouchier styles. 

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Tuck Skinny Jeans Into Ankle Boots

Jeans and ankle boots
Tuck skinny jeans into ankle boots. Kirstin Sinclair/Getty Images

Skinny jeans weren't meant to have anything layered under them. That's why tucking your skinnies into your ankle boots is a no-brainer. This combination looks great with your longer, snugger jeans that will reliably stay put when you wear them with a shorter boot.

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Don't Mind the Gap

Woman in jeans and ankle boots
Show off your ankle cleavage. Brett and Natalie Kaffee/Getty Images

Ankle cleavage is a thing now -- yes, really. To pull off this sexy look, match your go-to, dark wash skinny jeans with a high-heeled ankle bootie that dips at the front, to show off the top of your foot. This looks great when the boots are black, as pictured here.

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Roll Your Cuffs

Cuffed jeans and ankle boots
Cuff your jeans to show off great boots. Kirstin Sinclair/Getty Images

You should also think beyond the usual skinny jeans when you want to wear your ankle boots. When jeans aren't tight at the ankles, they're easier to roll up -- all the better to show off your favorite booties. So try wearing your favorite boyfriend jeans or a straight leg pair with ankle boots, cuffing jeans above the ankle. This look works with all ankle boots, but is especially great for those with a bit of a heel.

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Roll Your Cuffs - Thin Cuff Version

Jeans and ankle boots
Cuff jeans with an easy flip to flaunt your boots. Kirstin Sinclair/Getty Images

Here's how it looks with a more casually flipped up, skinny cuff and platform heel ankle boots.

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Give Hems a Trim

Raw hem jeans and ankle boots
Trim your jeans hems to show off fabulous booties. Timur Emek/Getty Images

Pull off that trendy frayed jeans look -- plus flaunt your favorite short boots -- by doing a quick DIY on your jeans hems. Just try my quick and easy method -- stand in front of a mirror, wearing your jeans and the ankle boots you want to show off. Use a piece of chalk or washable marker to mark the level where you'll cut. Then, remove jeans and use sharp fabric scissors to cut off the extra length. For a fashionable "raw hem" look, you can use a pair of pointy manicure scissors to pull at the threads around hems bottoms and encourage stragglers.

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Create an Instant (Clean) Hem

Ankle boots and jeans outfit
Fake a hem by folding jeans under. Kirstin Sinclair/Getty Images

If your skinny jeans are too long to show off your boots -- and too tight to roll up stylishly -- you can always try this tailor's trick. Simply fold your jeans hems inward, instead of upward, to create an invisible cuff. This style hack not only produces a more polished effect than rolled cuffs, which is great when you're dressing up, but it makes your jeans look like they've been custom altered to hit the perfect length. For you fusspots out there, you can do this trick before you put jeans on, and iron the hems to make sure your "cuffs" stay flat during wear.

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Match Your Boots to Your Denim

Black jeans and ankle boots
Rock black jeans and black ankle boots. Kirstin Sinclair/Getty Images

 Wearing skinny jeans with ankle boots is a great way to create an unbroken leg line, for a long and lean silhouette, especially when you match your jeans color to the shade of your ankle boots. For the skinniest effect, try wearing a pair of skinny, inky black jeans with black suede or matte black leather ankle boots.

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Try it With Cropped Jeans

Wear cropped jeans with ankle boots
Wear your cropped jeans with ankle boots. Matthew Sperzel/Getty Images

Here's an easy way to give those cropped jeans in your closet a style upgrade. Just flip up the cuffs once, to give them a boyfriend vibe when you wear them with ankle boots.

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Or Camouflage Crops With Socks

Skinny jeans ankle boots and socks
Wear socks to make cropped jeans seem longer. Kirstin Sinclair/Getty Images

Think there's no way to wear your cropped skinny jeans with ankle boots? There is -- just bridge the gap between hems and boot tops with tall socks. This is a look that's meant for casual weekend wear and is a great way to wear cropped jeans in those transitional months, when the weather is iffy.