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 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.
As I said above, this works best with a taller ankle boot. Leggings are ideal for tucking into ankle boots, and you can do it with skinny jeans if they are tight through the calf and ankle. The jeans I’m wearing here aren’t as tight as some, but the shaft of the boot is wide enough so it works. More details in THIS POST.
SALE ALERT >> Take 30% off full price denim at DL1961 with code DLOCT16
Ideally, I wear super skinny ankle jeans with my ankle boots and booties because there’s no extra material bunching up and making the boots uncomfortable.
Sometimes I cuff my jeans with these boots, but in this case I liked the cleaner look of letting these jeggings settle into the boots. Because they fit snugly to the ankle, I didn’t have to futz with them at all. More pictures and details in THIS POST.
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 and make your legs look stumpy.
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. More photos and details in THIS POST.
3. Try a single cuff.
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.
These are cropped jeans, so the cuff is very small. That’s fine too. You have to play around with them to see what looks best with every pants/bootie combo. More photos and outfit details in THIS POST.
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. More photos and details in THIS POST.
I love these black jeans against the taupe booties. The booties allow some skin to show, which (again) is slimming. More photos and details in THIS POST.
4. 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. In this case, I tried cuffing these aubergine skinnies and it didn’t look right to me so I just let them rest on top of the booties. Also worth nothing, these jeans are an inch longer than some of my others shown above. More details and pictures in THIS POST.
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.
5. 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 Ankle Boots with Bootcut Jeans
6. 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. I LOVE these Sam Edelman pointy toe flats.
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.
Here’s an example of mine from a few years ago. These jeans and boots are old, but it shows the proper length of bootcut jeans with ankle boots. The jeans are almost too long, but I would rather have them a tad too long than a tad too short.
How to Wear Ankle Boots with Skirts and Dresses
7. 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.
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.
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.
8. Try socks with your ankle boots for added interest. Again, this can be dicey because it does tend to chop up the leg, but play around with it. I like this combination of neutral colors and textures. It’s not monochromatic, but the colors are close enough that it doesn’t chop up the leg too much. I can’t find the original source for this picture. So sorry!
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!
* * *
Did you like this post?
This post contains affiliate links. For more information, see my About Page: Blog Monetization and Disclosure.