In 2020, ankle boots and booties are all the rage, but working out how best to wear booties with jeans of any sort can be difficult. There are so many different possible looks, and working out what works best with your favorite ankle boots is a challenge. The good news is that booties are incredibly versatile, and you can easily wear them with jeans of any style – black jeans, blue jeans, straight leg jeans, skinny jeans… the list is endless.

We have put together a guide to the fashions of 2020, and how best to wear boots with any kind of clothes. Whether you want to know the best boots with dress option or how to wear men’s fashion with boots, we have got the answer for you below. No matter what style you are looking for, we have got the answer to how to make jeans look good with your favorite booties. Read on below to find out everything you need to know about wearing boots with jeans!

Ways to Wear Ankle Boots with Skinny Jeans

How exactly you wear jeans with ankle boots will depend on the type of ankle boots you have chosen to wear. In general, if you have boots with relatively high tops, then it is best to wear boots with jeans tucked into your booties. If, however, you prefer to wear ankle boots with relatively low tops, then you will be better off wearing your jeans uncuffed or untucked from your boots. Jeans are versatile, though, so you can easily adjust whatever look you like to have with your favorite jeans. Boots and jeans are a good combination, and skinny jeans are among the most flexible jean options for wearing with booties or ankle boots.

Tucked into skinny jeans

If you are wearing taller ankle boots, then tucking your skinny jeans into your boots is the way forward. This way to wear boots with skinny jeans works best with really tight jeans, particularly legging style, where the leg hole at the ankle fits tightly around your ankle, and the denim is not too thick or multi-layered.

If there is too much material around the ankle part of your jeans, then the jeans will bunch up and look rucked and lumpy when you try to wedge them into your boots. They can also be uncomfortable if you try to wear them this way. If you think your jeans are going to bunch up and cause problems when you try to tuck them into your boots, then you will be much better off wearing them cuffed. We will cover cuffing jeans and how to wear booties with that style in the next section.

If your jeans are tight and straight, and you want a long, smooth line all the way down, then you can just tuck the ankles of your jeans into the top of your booties. It is simple and effective, and it looks great with higher topped ankle boots, as long as you make sure that the denim doesn’t bunch up.

Untucked from skinny jeans

If you want to wear booties with skinny jeans without tucking the jeans into the top of your booties, then it is time to experiment a bit. This is a more flexible fashion option, and there are many different ways to wear booties with skinny jeans without having to tuck them into the top of your ankle boots. That makes this option ideal for thicker skinny jeans with wider leg holes, or for low top ankle boots that don’t come up high enough to comfortably fit the bottom of your jeans into them. The best option is usually to cuff your skinny jeans, or perhaps to double roll them. You are looking to raise the ankle enough to leave a narrow strip of your ankle visible between cuff and boot.

This works best with standard ankle-length skinny jeans; if your jeans are longer, you will have to make a longer, thicker cuffed section. That can be a good look in its own right, with the right accompaniment and the right style of booties, but it can make the leg line look a little odd and crudely interrupted. The reason you want a little bit of your ankle to be visible is that it is the narrowest part of your leg, and showing some of it off can help to make your legs look longer and thinner.

The narrow width of your ankle is emphasized by the width of the cuff on your jeans, and the overall effect is one of longer and more elegant legs. In 2020, the single cuff roll is much more on-trend than the double roll. It is generally slimmer and a little longer and most jeans are a little shorter at the moment. However, this depends a bit on the rest of your outfit – if you are pairing this look with a relatively short top, then you can afford to use a larger cuff, shortening your leg line a little.

If your top is a longer one, then it is best to use a smaller cuff to keep your leg line as long as possible – a shorter leg line can leave your legs looking a little stumpy if you are in a top that makes your torso look longer! If your jeans are relatively short and your booties have a relatively low shaft, then you can wear your jeans uncuffed and just let them rest on the top of your boots naturally. They might bunch up a little here, but they should look fine as long as they are a good fit.

You can also wear your jeans pulled smooth over the top of your booties, as long as the ankle openings are wide enough to allow that without too much stretching. This can give a very long, smooth leg line, but it only works with the longer, looser end of skinny jeans!

How well this style works will depend on each individual pair of jeans and ankle boots you are wearing. There is no blanket statement that can be made about how to wear jeans with rolled ankles with booties, but it is a flexible enough look that, no matter whether you are wearing blue or black jeans, you can always experiment with different lengths of cuff and roll in order to create the lines that you feel work best with your favorite boots.

Try out different combinations and styles, and see what works the best for the look you feel most comfortable with!

Wearing Ankle Boots with Straight-leg Jeans

Straight leg jeans, and particularly cropped jeans, are increasingly popular in 2020. They are easy to get looking great with booties, and the amount of effort you need to put in to wear ankle boots well with straight leg jeans is much lower than it is when you try to wear skinny jeans with your booties.

What you are aiming for when you wear booties with straight leg jeans is a long, straight leg line running all the way down. That usually means allowing the hem of your jeans to extend down over the top of your boots so that the line is straight and does not cut off at the ankle. This helps your legs to look longer and avoids the risk of stumpy looking legs.

If you wear shorter straight jeans such as cropped jeans, which are very popular at the moment, then you will want to adjust the rest of your wardrobe to fit a little. Your booties will help to keep your leg lines looking long and straight, but you will want to shorten the shape of your torso a little to compensate for the shorter cropped jeans.

Wearing Ankle Boots with Boot cut Jeans

While you might think of them as out of date, boot cut jeans are actually coming back into style at the moment. They are a great, versatile choice for anyone to wear with ankle boots, and are particularly flattering for anyone with wide hips or a larger torso thanks to their shape. Bootcut jeans are one of the styles where the length of jeans matters the most when you are pairing them with ankle boots. It doesn’t matter whether you are pairing them with boots or with lower shoes.

You want the hem of your boot cut jeans to fall an inch or less from the ground, without brushing against the floor. Somewhere between a half-inch and an inch is generally about right! If you are pairing them with flat booties, then a pointed toe on your boots generally looks better than rounded boots, but if you prefer to wear booties with heels, then rounded toes look fine.

If your boot cut jeans are cropped, then it is a little more complicated to wear them properly with ankle boots. Follow the guidelines above for pairing cropped jeans with ankle boots, and you should get great results. Cropped boot cut jeans are relatively uncommon at the moment, though – you are much more likely to find cropped straight leg or regular boot cut jeans!

Wearing Boots with Leggings

Ankle boots and leggings are a great combination, and almost always look great, no matter how you wear them. Faux leather leggings are a favorite, as they look sharp and a bit dressy when combined with a nice pair of booties. Whether your leggings end at the top of your ankle boots or the boots rises up above the hem a little, they will look stylish and comfortable. Just don’t pull the hem down over the tops of your boots!

In general, you should treat leggings, much like skinny jeans, in terms of how you might want to wear them with boots. The advantage of leggings is the range of different styles and colors available, making it easy to find the perfect match for the rest of any outfit you might be putting together, no matter how casual or smart it may be.

Wearing Ankle Boots with a Dress

Ankle boots are a fantastic addition to a skirt or dress, bringing an older outfit bang up to date with almost no effort required. By combining ankle boots with a monochromatic dress or skirt, you can achieve a beautifully elegant, long, straight line and a sense of movement and style that is usually much harder to manage. A single color used on your boots, your legs, and your skirt gives an effortless style that always looks great. If you would prefer to combine your skirt and ankle boots with bare legs, then a pair of boots relatively close to your skin tone (whether that is light or dark) helps immeasurably for keeping those color blocks balanced out and smooth.

If you want to try combining sock booties with a skirt or dress, go for something with a higher hemline. The stark lines of the sock booties combine well with shorter skirts, giving a sense of well-proportioned legs despite the choppy effect of those high, tight ankles. As a general rule, lower ankle boots mean you want to wear a longer skirt or dress with them, while higher topped ankle boots need a higher hemline in order to keep the proportions and spacing looking right. To some extent, you can fudge this a little by changing how you dress your upper body to accentuate or reduce your torso length, but most of the work is going to have to be done in the space between ankle and hem.

About the Author

Hey, I'm Lilly Harvey. If there's two things I'm passionate about in life, it's shoes and writing!

Combining both my passions with my Fashion Design degree, I've helped create Shoe Adviser to help readers choose the best shoes for them, enjoy!

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