How to Wear Ankle Boots With Practically Every Outfit You Own (2023)

FAQs

What outfit can I wear with ankle boots? ›

In 2022 it's back stronger than ever, already spotted as the star of many great street-style looks, both in its full-length version and the ankle boot one.

Hot take: There's no style of footwear more versatile than the leather boot. Sure, I'm a little biased, but in truth, boots go with everything. Need a classy date night outfit? Pair slick chinos and a button-down with your go-to Chelseas.

You can wear them in any color or dress, and they'll look great. Of course, the style of ankle boots can dictate the look. Wide ankle boots, such as slouchy or Western styles, will make your outfit more casual, especially in opaque black materials.

Cuffing jeans works best with ankle boots, because the cuff will fall right at the top of your boots. You can cuff straight-leg jeans and boot-cut jeans. Alternatively, you can also wear ankle jeans or cropped jeans with ankle boots—the jeans will naturally fall at your ankles so you will not need to cuff them.

It's best to avoid wearing them sans socks, as to keep them smelling their very best, for as long as possible (and, of course, to prevent freezing your feet off when the temps drop). As it turns out, though, pairing ankle boots with socks can actually look very stylish, and fashion girls have nailed the combo to a T.

Technically, you can wear them during any season, but the two seasons that warrant their use the most are spring and fall. The in-between, mild temperatures don't really require winter boots, but they're too cold for summer sandals and maybe even flats.

Black just goes with everything.

A quality pair of black boots can be worn with everything short of a tailored suit or a tuxedo...and truth be told, will actually work with a tux if you get the right shine on them. That's almost always been the refrain when it comes to black vs. brown boots.

One look we've learned to fall back on is dresses with tights and boots. The simple combination makes for an easy way to take your warm-weather pieces into a new season altogether. With the addition of tights and ankle boots, even the floatiest slip can work under the right circumstances.

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Is it OK to wear ankle boots with leggings? ›

embrace Colors And Textures

Making printed leggings work with ankle boots is tricky business, but it absolutely can be done. Try to stick to classic black or dark brown footwear, to give your funky leggings a solid base. Then, add a textured knit in a complementary color up top.

For a long, lean line, tuck the pants into the boots.

This works best with legging jeans where the leg opening at the ankle is small and they fit snug to the leg. You don't want them to look bunchy. If they're going to bunch, you're better off cuffing them.

The first is to look for a pair of jeans that are slightly cropped so that they hit just above the ankle boots. Another way to make jeans that aren't cropped work with ankle booties is to do a messy roll so the jeans sit on top of the ankle boots.

Ankle boots at all are outdated

Although the seemingly controversial sock boot is generally a higher boot, it seems that shorter boots are on their way out overall. Per Who What Wear, ankle boots (and not just those with rounded toes) aren't as fashionable as they once were.

Your doctor may have you use a boot for 1 to 6 weeks. How long you wear it depends on how serious your injury is. Walking boots are removable, and most of them can be adjusted. Your doctor will show you how to remove and adjust your boot.

As a general rule of thumb, taller boots work best with knee or over-the-knee socks, while shorter styles (think trouser or crew socks) pair well with ankle boots or booties.

Wearing booties with cropped or ankle-length pants can create an incredible style, too. This is a great pairing for transitional looks in the fall and spring. One way to pull off the look with shorter trousers is to wear booties that have some type of cut-out, such as those with an open-toe style.

If you're wearing skinny jeans, tucking them into your boots are probably your only option. The good news is, you'll look great doing so! It's a fun and playful look. We don't suggest tucking in your jeans if wearing a bootcut.

If you're completely stuck and you're not sure which to choose, go with a standard brown pair of boots. You can always get a second pair in any color you want. But brown leather is going to give you the most versatility.

Should ankle boots be tight or loose? ›

Different styles of ankle boot will have a slightly different fit, but generally, your boots should fit nice and snug around your ankles without feeling too tight or too loose. One way to tell if your boots fit properly is to pop a finger between the back of your ankle and your boot.

What are some reasons to wear a walking boot? The walking boot protects the foot and ankle from different kinds of injuries such as sprain, shin splint, heel spurs, plantar fasciitis, and broken foot too.

Neutral-hued shoes are fantastic because they go with anything, including all colors, patterns, and prints. In this case, it's best to stick to basics like black, white, cream, beige, brown, and gray, or switch things up and choose navy, which, yes, is considered neutral, too.

Black, beige, and grey shoes go with anything. Since they are all neutrals, you can wear these colors to offset a more vibrant outfit. Of course, with these neutrals, you can either mix and match or keep them in a similar tonal family. For example, there can be warm beiges and cooler beiges.

TLDR: You can wear ankle boots with skinny jeans that are cuffed, tucked in, rolled under or with a pair of jeans that hits at the ankle. If your booties are short, don't tuck them in. If your booties are tall, they'll look best with tucked-in skinny jeans.

Your straight leg or skinny pants and jeans that end several centimetres above the top of your ankle boots are an ideal pairing. There's no need to make that space with a cuff or roll because it is already there.

Tuck Skinny Jeans Into Ankle Boots

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.

Ankle boots are the perfect pair of shoes for light downpours and paired with skinny jeans, they're a go-to outfit for most women.

Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you're rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

You've heard this tip before, and it's especially true for shorties. If you're wearing your ankle boots with boyfriend jeans, please, whatever you do, roll up your hem. The sweet spot is about a half inch above the boot, so a little ankle shows and elongates your legs.

How do you wear ankle boots in your 50s? ›

roll up and leave 1/2″ of ankle between the boot and your pant. You can fold over twice to have a narrow cuff or one large fold. Be aware, the wider the cuff, the shorter your legs will look. If you cuff your jeans, wear a shorter top to help elongate the look of your legs.

Tucked into a pair of knee-high boots

Pairing your skinny jeans with your knee-high lug sole boots is a prime example of combining old trends with new ones. How else are you going to show off your knee-high boots when it's too cold to wear shorts or a mini skirt? Skinny jeans to the rescue!

Leather ankle boots are a staple with all kinds of clothing, not just jeans. But ankle boots and bootcut jeans fit perfectly together. You just need to figure out what style you're going for in your look.

Black leggings and minimalist black booties will always look cool together, especially when worn with an oversize button down or chunky knit…or both. Don't be afraid to resort to the tried-and true if you're strapped for more out-of-the-box ideas. There's a reason these looks are considered classics.

Flat ankle boots match nicely to more casual dresses, such as a skater dress, t-shirt dress or a comfy sweater dress. Flat ankle boots make for the most comfortable ankle boots, and are perfect for day-to-day wear. They suit everyone and can look really stylish.