5+ Ways to Wear Ankle Boots With Straight Leg Jeans

I think we can all agree that ankle boots are a staple closet item and even more so in the Fall. Living in Canada, the Fall and Spring are the only times we really get to show these off and so I take full advantage of the slightly crispier weather to style my ankle booties in different ways.

If you’re having trouble styling your favorite ankle boots with a pair of jeans, keep reading! We’ll be going over the type of ankle boots, types of jeans (yes even the types of straight leg jeans) and then showing different options for styling your pair of booties with your different styles of jeans.

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The Types of Jeans

When it comes to jeans, there’s a wide range they come in based on their type of fit and cut.

The 8 main styles are:

-Skinny jeans
-Straight-leg jeans
-Bootcut jeans
-Wide-leg jeans
-High-rise jeans
-Mid-rise jeans
-Low-rise jeans
All the other jeans you may know would fall under one of these categories. For example, mom jeans tend to be high-rise in nature and so they would fall under high-rise jeans.

When talking about styling booties in this post however, the main jeans I would be referencing are skinny jeans, straight-leg jeans, bootcut jeans and wide-leg jeans. This is because we are more interested in the shape and flare of the jeans versus how they fit around the waist.

The style of jean you choose to wear is heavily influenced by your choice of boot and vice versa. As this post is focusing on straight-leg jeans, let’s start off by understanding the types of straight-leg jeans.

These types are:
-Skinny jeans
-Super skinny jeans
-Slim jeans
-Straight jeans and
-Taper jeans (a cropped length boot cut off right above the ankle bone).

One pair of jeans can fall under multiple categories as you can see (a straight jean could be mid-rise and tapered at the same time).

Now that we’ve got the different jeans down, let’s quickly go over the types of boots in terms of height.

This includes:
Ankle boots
Knee-high boots
Over-the-knee boots

As our focus is on ankle boots, we shall split these into the categories of: low ankle boots (like most booties), mid ankle boots (like a chelsea boot)and high ankle boots (like a combat boot).

Now that we’ve got the types of jeans and boots covered, let’s focus on outfit ideas for our straight leg jeans and different ankle boots.

1) Skinny jeans

Skinny jeans are probably the easiest straight-leg jean to style with an ankle boot. This is because you don’t need to tuck or roll the hem of your jeans up in order to complete the look, meaning there is no chance of bulking around the ankle.

When it comes to styling a look with a pair of ankle boots, you generally want the top of the boot to show.

If your jeans are too long, you should try to tuck or fold the hem of your skinny jeans into your boot and if the jeans are not straight, this can become a challenge. You might be left with some excess denim, making your look awkward.

Similar match HERE

Regardless of your body type, I would strongly suggest you invest in a pair of good skinny jeans if you tend to be rocking the ankle boot look across different seasons. They would give your outfit such a modern look and now skinny jeans are made to accommodate all sizes.

Sock boots are an example of ankle booties that could work only with a skinny jean because the material is so thin that anything thicker than a skinny jean would just bunch up and look really weird.

Get a similar look HERE

During the warmer months, you can throw on a pair of cut out black ankle boots to go with your skinny jeans and a leather jacket for a chic date night look.

2) Straight jeans

Straight jeans are sort of that jean in between a skinny jean and a boot cut. They don’t hug your ankles but don’t flare out at the bottom neither. These jeans are a great option for ankle boot pairing if skinny jeans are a big no-no for you.

They are still tuckable (if that’s a word) without causing bunching at the ankles of your boots. These jeans work great with pointy toe ankle boots as well as sock booties if you don’t mind leaving some jean over the top of the boot.

Straight jeans can be styled in several ways that can make them dressed up or down. Try wearing a blouse with a pair of dark-wash straight-leg jeans and then styling this look with a pair of ankle boots with a stiletto heel for a more formal look. Trench coats work amazing to finish this business casual look.

3) Taper Jeans

A lot of people think tapered jeans are only for the warmer weather but that is incorrect. Tapered jeans are the perfect option of jeans to go with a combat boot or a Chelsea boot. This is because these 2 styles of ankle boots rise a little higher, covering the hem of the jeans right at the top of your boots and allowing the boots to be on full display.

When you’re wearing Chelsea boots, like your Doc Maarten’s, you want them to be seen and so non-flare jeans work best here.

Adding a graphic tee to this look is a great way to really give your casual look some edge.

Taper jeans would also work nicely with heeled sock boots for a more dressed up look. In my opinion, the pointier the toe of the boot, the more dressed up it looks.

Tip: When considering these ankle boot choice, always keep in mind that your height plays a role as well. Ankle boots that cut you off closer to your calf tend to make you appear shorter while an ankle boot that reaches right around your ankle bone would make you appear taller.

When in doubt, add a bootie with a heel if you wish to elongate your legs.

I know this post is focused on ankle boots and straight-leg denim but I just wanted to seize the opportunity to quickly talk about some of the other denim styles and different types of boots.

If you have one, you tend to generally have the other so I might as well give you some more outfit combo ideas in one blog post.

Wide-leg and boot-cut jeans

Wider legged jeans can definitely still work with ankle boots, as long as you don’t mind not showing your cute booties off. The bottom of your jeans would most likely cover the top of your boots and all that would be seen would be the front of your shoes.

Black jeans, a moto jacket, a white tee and some large shades would complete this chic look.

If you have wide calves like myself, sometimes ankle boots are the only boots that you can feel comfortable in and you might be insecure about that (which you shouldn’t be!)

However, if you’re bent on not showing off your calves with one of the tucked in looks, wide-leg jeans are the best way to go.

Cowboy boots are a fun boot to go with if you’re strutting in some bootcut jeans. This outfit combo works in the Fall as well as in the summer if you’re in Texas 🙂

If you do end up wanting to try tucking in your straight-leg jeans, you can ease into this style by starting with your shortest ankle boots and pairing those with your skinny jeans.

The lower cut of the boots gives some distance between your calf and your ankle, adding length to your foot and not drawing attention to your calves.

Try it and let me know how it works out for you!

I hope you’ve gotten lots of outfit ideas you will use when pairing your ankle boots with not only your straight-leg jeans but also all the other jeans you have in your closet. Remember that this a style guide and the best option of ankle boots would depend on the jeans and vice versa.

Skinnier and/or cropped jeans work with both lower and higher ankle boots because of how easy it is to tuck in while flare jeans or wide-legged jeans work better with lower ankle boots because no one is seeing the top of your boots.

Feel free to play around with different colors of boots but my general rule is: the darker the color, the more formal the look. Black boots can be worn to both the office and to formal events while I don’t see a bright red boot being worn to a board meeting.

If you’re on the shorter side and wish to elongate your legs, ty not to cut yourself off at the calf but leave room between your ankle and calf. Or you can just wear a wider-legged boot and not tuck in.

You can check out how to style only your flat ankle boots HERE or how to style a pair of brown boots.

Looking for some more tips such as what shoes to wear with a burgundy dress?

Or searching for the perfect minimalist bag to go with your outfits?

I got you covered!

See you on the next post!


P.S. Don’t forget to follow me on LTK to keep up with all my latest fashion finds and daily style inspiration!

For those of you looking for ideas on which shoes to pair with your bell bottoms, check out my post: 12 Shoes to Pair with Bell Bottoms or Flare Jeans.

My blog post: The 15 Best Pants to Wear with Ankle Boots is a great guide on deciding the types of pants and jeans to pair with ankle boots.