How to Wear Ankle Boots

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!

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 with some examples from Pinterest.

How to Wear Ankle Boots This Fall

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. 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.

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

Vince Camuto Feina Booties // LOFT Sateen Five Pocket Leggings

2. Cuff or double-roll your skinny jeans allow a hint of ankle to show. 

This works best with ankle-length 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 and make your legs look stumpy.

How to Wear Ankle Boots - cuffed with Toms Desert Booties

Toms Desert Bootie // skinny jeans (similar for less) // similar utility jackets // similar scarves // Dooney & Bourke totes // Tory Burch Sunnies

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. Another way to do this is to wear booties the same shade as the pants. In this case, my jeans are a light wash and so are the booties, so even though I cuffed them and wore them with a longer top, I remain in balance.

How to Wear Ankle Boots -- Cuff your ankle skinny jeans.

Vince Camuto Feina Booties // AG Raw Hem Legging Ankle Jeans (similar for less)

I’ve worn these jeans with these boots both ways — single cuffed and double cuffed. They work either way. It’s purely a matter of preference.

How to Cuff Jeans with Booties

I love these black jeans against the taupe booties. The booties allow some skin to show, which (again) is slimming.

How to Wear Ankle Boots -- Single Cuff Black Skinnies with Taupe Cut-Out Booties

3. Let them fall to the top of the boot and bunch or rest on top. I find myself doing this mostly with lower shaft booties.

How to Wear Ankle Boots with a Low Shaft

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. But I cannot stress enough the importance of trying them different ways in front of your full-length mirror until you find the perfect combination. Just remember, letting some of your ankle peek out when you cuff helps visually elongate the line of the leg.

How to Wear Ankle Boots with Straight Leg Jeans

I’m adding this section in response to a comment below. I should have covered straight leg jeans, but I tend to forget about them. If you have a curvier figure, you may not feel comfortable in skinny jeans, but straight leg jeans are an option. Bootcut jeans may flatter you better, and I do cover them below.

4. 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 from the Shopbop website. These jeans have been sold out but this is how I would style straight leg jeans with ankle boots.

How to Wear Straight Leg Jeans with Ankle Boots

How to Wear Ankle Boots with Bootcut Jeans

5. The most important factor 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.

Don’t rely on shopping websites to show the right length. Often the models wearing the jeans are too tall and they show the jeans too short. These Joe’s Curvy Bootcut Jeans are perfect. Of course they are showing them with pumps, but they should look the same with booties. These are a similar style for less.

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

Here’s an example of mine. I wouldn’t want them any shorter than this.

How to Wear Ankle Boots with Skirts and Dresses

6. To keep a slim line, go for a monochromatic look. This is especially helpful when wearing ankle boots with skirts. I don’t have any personal photos so I’m borrowing a few from Pinterest. Here’s an example of a black skirt, black tights and black ankle boots.

how to wear ankle boots with a skirt

Or if you like to go bare, stick with ankle boots that are close to the color of your skin so your legs don’t look chopped off at the ankle.

How to Wear Ankle Boots with a Dress

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. More details in THIS POST.

How to wear a denim skirt with ankle boots

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!

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