How to Wear Booties With Different Cuts of Jeans

Let’s talk about how to wear booties with different cuts of jeans. Several years ago, I wrote a series on how to wear jeans with ankle boots, but at the time I only focused on skinny jeans. With denim trends shifting, I know a lot of you are trying to figure out how to make jeans work with booties all over again, so here we are!

If you have questions about how to wear booties with different cuts of jeans, you are definitely not alone! You’ve heard me say that style is like a puzzle, and great style starts with having the right pieces of the puzzle. I find that truer than ever when it comes to booties and jeans. With ankle boots, there are more variables that you have to account for than with other shoes to fit properly with jeans, namely how tall and how wide the shaft is relative to your own legs and to the legs of the pants. So the puzzle pieces require more nuance and more attention to detail!

Today we’ll dive into some things to look for when trying to wear booties with different cuts of jeans. BTW, I’ve already written a couple of posts on straight leg pants and shoes that you can check out for further reading:

Some of what we cover today will be repeated from those posts, but I think it’s helpful to have it all in one post, so here we go!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes. At the bottom of this post, I will link to any items that are currently available or similar items. 


Main Goals When Pairing Booties With Jeans

My main goal when it comes to pairing booties with jeans is to try and keep the leg line long and streamline. It doesn’t matter which cuts of jeans we’re talking about, I aim for that every time, so everything I’ll share here will have that goal in mind.

My other goal is to keep things as simple and as versatile as possible. I really dislike having a pair of shoes that only works with one specific pair of jeans. I want each of my shoes to work with multiple pairs of pants, and vice versa. I don’t know about you, but I don’t want to think so hard about getting dressed!

So, while there are many other pairings of jeans with booties that you could do in addition to the ones I show here, I’m going to stick with the most universal ones to help you choose shoes and jeans that will work in more versatile ways.


Skinny Jeans With Booties

While skinny jeans are moving out of the spotlight, they are still great options. And really, they are kind of necessary in some cases, regardless of what the trends are. Like, when it’s really cold and you need to wear all-weather boots or tall boots to keep your legs warmer, skinny jeans are the simplest and best option, so they’re still relevant from a practical standpoint! (Just pair them with modern pieces on top if you’re worried about looking outdated.)

My favorite way to wear skinny jeans with booties is below:

How to Wear Skinny Jeans with Booties: White sweater + medium blue skinny cuffed ankle jeans + taupe booties + gold pendant necklace

I like when the bottom of the pant leg is really fitted and creates a fairly uniform line with the top of the booties. I also aim for there to be a slight gap between the booties or for the pant leg to have a cuff that is a different color than the outside of the pants, or both. The picture above has both.

I personally prefer not to have my skinny jeans bunch at the bottom, as I like how a neater line looks a bit more polished. I also prefer a fitted leg opening as opposed to a wider leg opening, as I feel the latter can cut off your legs. Examples below:

How to Wear Booties With Different Cuts of Jeans - Skinny Jeans

I don’t think the other two options are the worst things ever, but I definitely prefer the last look. Also, for the second look, I don’t mind if the jeans are slightly wider than the booties, but I do try to avoid an extreme version. I think I don’t like it with skinny jeans because the calves are fitted on skinny jeans, so when the cuff is noticeably wider, it creates a wonky line down the leg. (As a note, this is particular to skinny jeans. When we get to straight leg jeans, you’ll see that a pant leg that is wider than the boot looks fine because the calves aren’t as fitted, so the vertical line stays straight.)

Troubleshooting the Look:
There are a couple of main factors to troubleshoot when the pieces don’t work together:

a) the leg opening of the jeans is too wide

b) the shaft of the boot is too high, causing you to have to roll your jeans up so high that it cuts off your legs or roll them up too much and add width to the cuff

What I Look for When Pairing Skinny Jeans With Booties
If you want to be able to cuff your jeans while not cutting off your legs and while keeping a streamline look, here are two things I look for:

a) Jeans that have very fitted ankles. (You can also take the jeans to a tailor to get the leg opening narrowed.)

b) Boots with a lower shaft so that I don’t have to roll my jeans up as much. Whenever I’m considering a pair of boots to wear with skinny jeans, I check if it works with my go-to skinny jeans. If it does, that’s an easy decision. If it doesn’t, I have to spend more time thinking through whether it’s worth having them in my closet if they don’t work as easily. (Usually my answer is “no” because I prioritize ease and functionality most of the time. But that’s just me!)

Alright, we talked through a lot, and while it can seem confusing when it’s all laid out like that, it really boils down to a couple of things: the fitted ankles and the lower shaft. If you focus on those two things, everything falls in place more easily. And, it’s much, MUCH quicker to get dressed!


Bootcut Jeans With Booties

Bootcut jeans are fairly straight forward because they are made for boots. (Hence the name!) The bottom of the legs is slightly wider to make room for boots. I do have two recommendations for bootcut jeans, though.

First, I recommend wearing bootcut jeans with booties that have a little bit of a heel. Bootcut jeans are cut in such a way that they are meant to be worn with a heel. They can make your legs look a million miles long. That said, you don’t *have to* wear them with a heel, but if you feel like bootcut jeans look messy or aren’t doing their magic when you’re wearing flats, it’s probably because of the flats. (Not because anything is wrong with your body!) Try them with something that has a slight heel and see what it does.

My second recommendation is to wear booties with a bit of an elongated toe box, whether that means a pointed toe or an almond shape toe. Sometimes feet can look swallowed up in bootcut jeans, especially if the bottom is particularly flared or wide, and a shoe with an elongated toe will help to extend your leg line. (Although I’m wearing a pointed toe boot in the picture below, I personally prefer almond shape toes to pointed toes most of the time. Almond toes work better for my more relaxed style while still giving you the benefits of an elongated toe! An example of an almond shaped toe boot is the pair I’m wearing in the ideal skinny jean outfit above.)

How to Wear Bootcut Jeans with Booties: olive green floral top + cream cardigan + dark wash bootcut jeans + taupe booties + cognac tote + white leather earrings + gold pendant necklace

In the picture above, the heel is about 1-1.5″, so it’s not very tall, but it’s a slight heel nonetheless, and it helps!


Straight Leg Jeans With Booties

Now we move to straight leg jeans. When it comes to wearing straight leg jeans with booties, I feel like more nuance is required, similar to skinny jeans.

Length of the Jeans
First, let’s talk about the length of the jeans. For straight leg jeans, I prefer for them to be either:

a) ankle length, sitting at the top of my ankle bone or within about 1″ above, or

b) right at the top of my foot / middle of my instep if we’re talking full-length

These lengths allow you to keep that long, clean leg line once you pair them with booties.

What to Aim For
Again, my main goal would be to create a long, clean leg line. In other words, I’m trying to avoid my jeans getting caught and bunched up on my ankle boots when I move around!

How to Wear Straight Leg Jeans With Booties
There are a couple of options. First, you can have the jeans sit right on top of the booties. To do that, you have to make sure the length of the jeans works perfectly with the shaft height of the booties so that the jeans don’t get caught on the boot.

Second, you can have your pant legs fall over the boots. In order to do that, you have to pay attention to:

a) the width of the leg opening

b) the shaft of the boot, making sure the booties have a tall enough and narrow enough shaft to fit—and stay(!)—under the pant legs 

So, while I said that with skinny jeans I look for booties with a lower shaft, with straight leg jeans, I look for booties with a higher shaft and a narrow shaft. (And yes, I totally think it’s annoying to essentially have to buy all new shoes. 😭)

How wide the legs of the pants are and how long they are determine how narrow and tall the shaft of the boot needs to be. For example, if the leg is slimmer and shorter, then you’ll need boots with a shaft that is slimmer and taller to fit under the pant legs. I usually aim for pant legs to cover the shaft of the boots by 1-2″ so that they remain over the boot when you move around.

Examples of Booties With Straight Leg Jeans With Different Leg Widths

Let’s take a look at how the width of pants affects how they pair with booties. We’ll look at pairings with slim straight leg jeans and then wider straight leg jeans.

Slim Straight Leg Jeans With Booties
Here is the same pair of jeans paired with booties that have three different shaft heights. Under each outfit I showed the three boots I’m wearing so that you can see the difference in how tall the shaft is.

How to Wear Straight Leg Jeans With Booties

The pair of booties in the first picture (a) have the shortest shaft. That is the SAME pair of boots that I used in the *ideal* version of skinny jeans. They were perfect for skinny jeans, but they aren’t great with these straight leg jeans—the pants are getting caught on the boot.

The second picture shows jeans with booties that have a slightly higher shaft. The shaft is also fairly narrow, so it does fit under the pant leg. However, it sort of bunches, and while it’s not horrible, it’s not my favorite either. These boots might work with a different pair of straight leg jeans, but I don’t love it with this pair.

The third picture shows jeans with booties that have a taller and narrower shaft. They fit more easily under narrow pant legs and create a more streamlined look. Yes!


Wider Leg Straight Jeans
Now let’s show some boots with straight leg jeans that have a wider leg. A wider leg is able to fall more easily over a variety of booties. They work with booties that have a narrower shaft, but they can also fit over booties with slightly wider or lower shafts. Overall, these afford you a little more flexibility with your shoe options, depending on how wide the leg is. Here are some examples:

How to Wear Booties With Different Cuts of Jeans - Wide Straight Leg

The first example is of straight leg jeans paired with the same booties as in the ideal skinny jean example and the first not-ideal slim straight leg example. Here they are, though, with a pair of wider leg straight leg jeans. Because the leg opening is wider, the pants don’t get caught on the boots like the slimmer straight leg jeans do. Also, even though the pant leg is much wider than the booties, unlike with the wider cuff on skinny jeans, the line looks more fluid and cleaner with straight leg pants—because straight leg jeans fall straighter around the calves whereas my skinny jeans created curved lines at the calves.

The second example shows straight leg jeans paired with the same booties as in the ideal slim straight leg example. The shaft of these boots is really narrow, so of course they work with jeans that have a wider leg opening.

WHEW! Is anyone else tired? 🤪 Figuring out how to wear booties with different cuts of jeans can be work, but the work is easier when you know which puzzle pieces to look for. I hope this helped you hone in on some key characteristics to look for in booties and jeans so that styling them becomes a little simpler!

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