Ankle boots are a must-have in the chilly season, and we’ve got the lowdown on the best jeans to rock with them.

As the temperatures drop, these little darlings become our favorite companions: ankle boots! These trendy kicks not only keep our tootsies warm, but also work their magic to give us svelte ankles. What’s more, you can style booties in countless ways, from a flirty skirt or dress to classic old pants.

woman over 50 with short grey hair wears white ankle boots with short cropped jeans

One classic combo that never goes out of style? Jeans and ankle boots. But not all jeans play nice with boots. Some pants are just too long, others too baggy, and some are simply a mismatch in style. So, we’ve cracked the code and found the perfect pair of jeans to strut your stuff in those booties.

Cropped Straight Leg Jeans are the BFF of ankle boots

what jeans to wear with short boots

Skinny jeans and ankle boots – a fall and winter staple, right? Well, it turns out that those super-skinny pants might not be the best match for your booties. Sure, they eliminate the awkward tucking of pants into your boots, but they can accentuate those trouble spots on your thighs and calves.

If that’s not your jam, consider swapping out those skinny jeans for a Cropped Straight Leg pair. These pants, with their shortened hems, are like the booties’ besties. They’re the Goldilocks of jeans – not too tight, not too loose, just right, especially around the calf area. And a little flare at the hem is totally welcome.

black skinny cropped jeans paired with ankle boots

The cropped length draws the eye right to the slimmest part of your leg – the ankle, making your entire silhouette appear slimmer and longer. Bonus points: your booties will shine like the stars they are.

Also interesting: How To Choose Flattering Boots For Your Body Type

How to wear ankle boots with cropped jeans

how to wear straight jeans with ankle boots

Whether it’s Chelsea boots, with or without heels, sock-boots, or some rugged biker style, there are ankle boots for every taste. What matters most, though, is the length of your jeans. They should end just above your boots, leaving a sliver of skin to peek through if possible.

Styling tip: Want those legs to look extra long? Go for pointy-toed booties with slim heels. On the other hand, sock-boots are the way to go if you want to create a slimmer leg illusion.

biker boots paired with cropped straight leg jeans and long winter coat

Now, when it comes to styling, you’ve got the green light to mix and match to your heart’s content. Jeans and ankle boots are your blank canvas for various looks. Go elegant with black leather heels and a blazer, or keep it casually cool with lace-up biker boots and a leather-look shirt.

Our pro tip: Combine different styles – try biker boots with a ruffled blouse or distressed jeans with stiletto-heeled booties. It’ll spice up your look and keep things interesting.

As for tops, the harmony rule is simple. Tops that end just above your behind work like a charm with ankle boots and jeans. If your top is too long, you’ll lose that flattering lift effect. Long tops should be tucked in or partially tucked to maintain those lovely proportions.

beige suede booties and straight leg cropped jeans

About the Author Jaylee Burmer

Jaylee always brings positivity into every room she enters! She is passionate about writing since 2015 and loves to share her thoughts with the world. Her posts range from topics such as fashion, lifestyle, travel and health & wellness - all with an inspiring twist!

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