How to Wear Ankle Boots {2019}

This post on how to wear ankle boots is one of my most popular, but I do believe it is time for an update! There are soooo many styles of ankle boots and so many styles of jeans that it is a bit of a sticky wicket, figuring out how to style your ankle boots, so I’m here to help!

I’m sharing 5 ways to wear ankle boots in this post, along with pictures and explanations. First we’ll talk about how to style ankle boots with various types of jeans, and then I will touch on dresses and skirts at the end. I hope it’s helpful.

Most Recent Update: January 2019

How to Wear Ankle Boots for 2019 with real life examples! How to style ankle boots with skinny jeans, straight jeans, bootcut jeans, leggings, and dresses!

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Okay, so back to ankle boots… These pictures are meant to be examples so you can come up with similar combinations from your own closet, but I do link to the items shown (or similar if they’re old.) But by all means, shop your closet or your favorite retailers for similar styles if some of my examples are out of budget.

How to Wear Ankle Boots with Skinny Jeans

Generally, boots with a taller shaft look best with skinny jeans tucked in, and boots with a lower shaft look better with jeans untucked or cuffed. Let’s break it down.

#1. Tucked Into Skinny Jeans 

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. (See #2.)

How to Wear Ankle Boots - tucked into booties with a higher shaft

similar taupe booties // sateen skinny pants

In this next example, the leg opening of the jeans is a little wider than the ones above, but the opening at the top of the boot is also a bit bigger, so it allows the jeans to sit inside without bunching.

I tried cuffing them first, but I felt like that shortened the line of the leg and made me look stumpy, so I opted for this method.

How to wear ankle boots with skinny jeans tucked in.

ivory turtlenecks // wool reefer // similar scarf // skinny jeans (option) // similar booties  // leopard clutch

Here’s one more example. These “slouch boots” have a higher shaft and a wide opening, so I wear them over my skinny jeans as you can see here.

leopard print scarfs // leather jackets // layering tee // skinny jeans (option) // slouch boots // black satchel

#2. Untucked with Skinny Jeans

This is when you really have to experiment with the style of bootie and the length of your jeans to see what works best.

Cuff or double-roll your skinny jeans allow a hint of ankle to show. This works best with ankle-length skinny jeans. If the jeans are super long, there is a larger cuff, which can work, but it can also cut off the leg line in an awkward way, so it takes some trial and error to decide what works best for every combination of jeans and booties.

suede moto // mockneck sweater // AG legging ankle jeans (budget option) // snakeskin booties (budget option) // necklace // earrings // bucket bag

This works because it makes the ankle look slimmer. Generally you want a bit of your skin to show because this is the narrowest part of your leg, and showing some skin helps prevent your legs from looking stumpy. Sometimes mine end up on the top of the boot as I walk around and my pants settle, but that’s okay.

I feel like the single cuff is more current at the moment. I’m seeing it more than the double, but sometimes it depends on the length of pant, as well as the length of your top. If your top is shorter, you can afford to “shorten” the leg-line with a larger cuff. If your top is longer, you want to keep the line of the leg as long as possible.

Here’s another similar example with white jeans and cognac booties.

white skinnies // similar booties

You can also just let your jeans fall to the top of the boot and bunch or rest on top. This works best with lower shaft booties.

hooded puffer vest // grey turtlenecks // black jeans (option) // booties // ring handle tote

In the next example, these jeans with the split hem don’t really allow cuffing, so again, I paired them with a lower shaft bootie — you can see that I let them fall into the back of the bootie, but in front, there is some skin showing between the hem of the jeans and the top of the bootie.

Jo-Lynne Shane wearing AG The Legging Ripped Ankle Skinny Jeans, Jeffrey Campbell Vanhook booties, Rails plaid shirt #Nsale 2018

plaid shirt (Ivory Bluebell Pink) // jeans // taupe booties

Leave them out over top of sock booties or any bootie with a taller, narrow shaft. I often wear my black sock booties with black ankle skinny jeans for a long, lean leg line.

Jo-Lynne Shane wearing AG black the legging ankle jeans, Everlane the cashmere v-neck, Everlane day market tote, Club Monaco sock booties

v-neck sweater // black skinnies // sock booties // tote

Whether or not you cuff your jeans depends on the length of your jeans, how snug they are to your ankle, the height and style of your boots, and yes, even your top! I KNOW! So many variables. This is why it’s important to try them different ways in front of your full-length mirror until you find the perfect combination.

#3. With Straight Leg Jeans

Straight leg jeans are trending this fall 2018, particularly the cropped styles. The good news is, these styles look great with ankle boots! And you don’t have to work quite as hard to find the right combination of length of jeans and height of boot shafts.

When wearing straight leg jeans with ankle boots, try to achieve one long, lean leg line. To do this you may need to allow the hem of the jeans (whether cuffed or un cuffed) extend over the shaft of the boot so they don’t cut off your leg and make it look stumpy. Here is an example of how I styled a slim straight ankle length jean with suede block heel booties.

color block sweater // straight ankle jeans // similar booties // bag

Because I haven’t experimented a ton with this look, I’m going to share a few other examples from the Nordstrom website. But first, a caveat. Do not rely on retail websites to show the proper styling of boots and jeans. Most models are super tall, and they generally don’t alter clothes to fit them properly when shooting looks for the website pictures, so I find a lot of times denim lengths are off. However, I found a couple examples that I believe got it right.

In this example, there is a little bit of skin showing between the hem of the jeans and the top of the ankle boots — this works, but you don’t want them to be any further apart, or it will chop up the line of the leg too much. (Here is an example I think shows too much space between the jean and the boots.)

Also, because there is low contrast between the light wash denim, the pale skin of the model, and the white bootie, you get a long, clean leg line even though it’s chopped up by the jeans and boots being separated.

straight leg jeans // similar white ankle boots

In this next example, the hem of the jeans extends over the shaft of the ankle boot by about an inch, allowing for a smooth transition, even though there is high contrast between the mid-wash denim and the black booties. This works without shortening the line of the leg too much, especially because the higher rise extends the jeans a couple inches at the top, compensating for the shorter leg length. It’s all about balancing the proportions! This is why it works best to wear a cropped top or to just tuck in the top when wearing cropped jeans.

Of course, if you are short-waisted, tucking isn’t always best. This is the issue I’m having with this trend. I find the shorter, boxy tops look best on me because I can leave them untucked. (See the example above.)

I think this look also works well because the high-heeled, pointy-toe ankle boot is slimming and helps to visually lengthen the line of the leg. A flat boot might not work as well.

high waist ankle straight leg jeans // similar ankle boots

Sock booties also work great with the straight ankle and straight crop jeans that are trending. Here is an outfit with the same jeans as above, but with black sock booties, a grey sweater, and black leather jacket.

Jo-Lynne Shane wearing Frame Le Slender Straight ankle jeans with Club Monaco black sock booties, Vince crewneck cashmere sweater, and Bernardo leather jacket

grey sweaters // leather jackets // straight ankle jeans // sock booties // double horn pendant // long horn pendant

#4. With Boot Cut Jeans

Bootcut jeans are trying to make a come-back this year, in both cropped and full-length styles, and the best part is, they are pretty much universally flattering — especially if you’re trying to balance out wider hips or a larger upper body.

The most important factor when wearing ankle boots with bootcut jeans is the length of the jeans. When pairing shoes with bootcut jeans (any shoe – not just ankle boots) the hem of the jeans should come within an inch of the ground without touching the ground. I prefer mine closer to 1/2 inch from the ground. I also think bootcut jeans look best with a pointy-toe boot or shoe because it elongates the leg, but you can wear them with a rounded toe if you prefer. I also prefer my bootcut jeans with heels, but again, flats are an option, but in that case a pointy toe definitely helps.

Again, don’t rely on retail websites to show the right length. Often the models wearing the jeans are too tall for the jeans they are modeling, but I rounded up an example that I think got it right. Of course they are showing them with pumps, but they should look the same with booties.

The proper length for boot-cut jeans and more style advice for women over 40 at jolynneshane.com!

Joe’s Curvy Bootcut Jeans

Here’s an example of how I wear mine.

How to wear bootcut jeans with ankle boots for 2017

floral blouse options // bootcut jeans  // similar booties

When pairing ankle boots with cropped bootcut jeans, the rules for the straight crop jeans apply. I’m not seeing these as much these days — the straight crop look seems to be more popular with the younger set.

Personally I prefer skinnies with ankle boots, but I hear they’re on their way out… Only time will tell, but so far, I’m not seeing any indication of that in my Instagram feed.

#5. With Leggings

Ankle boots can be really cute with leggings — especially faux leather leggings for a dressier look. Here’s a holiday look with faux leather/ponte leggings, a turtleneck tunic sweater, and black suede ankle boots. In this case, the leggings just meet at the top of the ankle boots, but it’s okay if the ankle boots come up over the leggings too.

tunic sweater // leggings // booties // clutch

#6. With dresses and skirts

Ankle boots are a great way to update a classic skirt outfit. To keep a long, lean line, go for a monochromatic look. Here’s an example from Pinterest of a black skirt, black tights, and black ankle boots.

how to wear ankle boots with a skirt and tights

If you like to go bare and worry about chopping up the line of the leg too much, stick with ankle boots that are close to the color of your skin so your legs don’t look chopped off at the ankle. I tried this look with a denim skirt and really liked it.

These taupe booties are close to the color of my skin so they don’t chop up the leg too much. Also, the shaft is high and rather narrow, keeping my ankles looking slim, so they work well with skirts and dresses.

How to wear a denim skirt with ankle boots

denim pencil skirts // stripe v-neck tees // taupe booties // crossbody // leather jackets

Here’s another example. These booties aren’t quite as close to the color of my skin, but they’re light enough to still provide a low contrast so they don’t chop off the leg at an awkward place.

cardigans // v-neck tee // utility skirt // taupe booties // satchel

Sock booties are also trending right now, and they work great with dresses. Here’s how I wore mine with a black shift dress. In theory, these chop up the line of the leg, but somehow the proportions seem to work because the dress is shorter, showing more leg.

how to wear sock booties with a dress

black bell sleeve dresses // sock booties // leopard clutch

So there you go! Figuring out how to wear ankle boots can be challenging, but once you get used to them, I think you’ll find that they’re quite versatile. Play around with them, and don’t be afraid to try something new!

How To Wear Ankle Boots for 2018: with skinny jeans, cropped straight jeans, bootcut jeans, and skirts!

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