jeans and boots outfit

How to Flawlessly Execute a Jeans and Boots Outfit

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Both jeans and boots are classic pieces on their own. Wear them together and you have a no-fail outfit combo for different seasons, occasions, and styles. A jeans and boots outfit is versatile and easy to mix and match, but it does come with a few guidelines in order to help you wear this style right. Here’s how to flawlessly execute a jeans and boots outfit!

shop a similar look: hat | jacket | jeans | boots

When it comes to wearing boots with jeans, you may feel a little overwhelmed at first, because there are so many different styles- of each!

When it comes to boots, here are some of the top styles:

  • Chelsea boots
  • Combat boots
  • Ankle boots
  • Knee-high boots
  • Thigh-high boots

Cowboy boots have recently come into the picture as something trendy, and though they can be fun for the right person, I don’t consider them a classic piece.

And when it comes to the style of jeans, there are many options as well such as:

  • Straight leg jeans
  • Cropped flared jeans
  • Skinny jeans
  • Slim jeans
  • Boot cut or flare jeans
  • Mom jeans
  • Boyfriend jeans
  • Baggy jeans (also dad jeans)

With all of these options, it’s no wonder you may have questions such as what jeans to pair with what boots and how!

If you want a safe option, go with skinny jeans.

Skinny jeans are the easiest way to rock a jeans and boots outfit. Because the leg is skinny, it can work with shorter styles such as ankle boots all the way to over-the-knee boots.

If you want a no-fuss way to wear this combo, then skinny jeans are the best option. The best boots to try out a jeans and boots outfit are ankle boots. They can be worn in many different ways and in many different styles.

Keep in mind that there are different boot heights too, and I’m not talking about the heel! Though we sometimes use these words interchangeably (myself included), there is a difference between certain ankle boots. And that difference is decided on where the shoe falls on your leg.

There are short/ “low” boots, where the top of your boots hits right at or right below the ankle. These are booties.

There are “medium” ankle boots, where they hit 1-4 inches on or above your ankle. This is what we generally consider ankle boots.

Then there are “tall” ankle boots, which are actually more mid-calf-length boots. These can be a challenging silhouette to pull off, based on where they land on your leg.

Knowing this is helpful when you need the right words and phrasing for online shopping, though knowing the terminology isn’t going to change your fashion life or anything. Just like learning algebra in school. Sure, it’s important, but have we really used it all that much in our day-to-day lives? 😉

You may be wondering, “Should I cuff my skinny jeans with my boots?” At the end of the day, it’s a personal preference. Personally, I think it’s a little outdated, but there are pros to this style, as you can adjust the hem of your jeans to best flatter your height and outfit.

Though I’m all for the classics of skinny jeans and ankle boots, don’t stop there! Though the other boot styles and jean styles take a bit more practice and thought, you can create a stylish look by mixing it up and trying something new.

Second to skinny jeans, I think the easiest pair to wear this style with are cropped flared jeans. They work best with ankle boots and it’s a classic Parisian girl favorite!

Related: How to Wear Jeans Like a French Girl

They just happen to be my personal favorite as well. Not only is it a great way to emulate French fashion, but it’s a classic style and the ankle-length of the jeans usually fits seamlessly over many ankle boots.

Just try on your outfit before heading out the door to make sure that the top of the boot fits under your jeans. You don’t want the jeans catching on the top of your boots if you can help it! Look for a jean inseam that stops an inch or two above your boots.

Here’s a crash course on the jeans and what boots you can wear with them.

Chelsea boots

  • Do: Wear with skinny jeans, slim, straight, cropped flare
  • Don’t: From skinny to baggy, all jean styles should work, just try them on first as each jean and boot style differs from retailer to retailer

Combat boots

  • Do: Skinny jeans, slim leg jeans, cropped flared, boot cut
  • Don’t: Since this boot is tight and clings to the leg, it should work with the majority of jean styles

Ankle boots

  • Do: All!
  • Don’t:

Knee-high boots

  • Do: Skinny, slim, bootcut, or straight
  • Don’t: Cropped flared, baggy/dad jeans, mom jeans

Over-the-knee boots

  • Do: Skinny
  • Don’t: Slim, straight, cropped flared, wide, or anything else (unless the shaft of your boot is wide and loose)

Just like ankle boots, thigh-high boots and over-the-knee boots are almost the same, with just a few differences. Mainly, thigh-high boots are a few inches taller than what is classically considered over-the-knee boots.

A thigh-high boot will be able to reach, you guessed it, your thigh, while an over-the-knee boot will not be able to go that high. I personally like this style, but I know they are not for everyone. In this post, I talk more about that style of boots and how to wear them in a chic and classic way!

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Now that you have a crash course in the different jeans and boot styles, rest assured that your knowledge isn’t going to go to waste because your jeans and boots outfit can work for any time of year!

In the spring and summer, opt for white jeans and a low bootie. Wear lighter colors such as a white tee or a pale pink anorak jacket.

In the fall, break out the darker colors and washes, such as brown boots and black jeans. Throw on a black leather jacket for a stylish layer.

When it comes to your winter outfits, most of your fall clothes will still work, though you may find yourself breaking out the taller boots and swapping out a basic tee for a long sleeve tee.

Related: A Winter Capsule Wardrobe That Will Never Go Out of Style

When shopping for your boots and jeans, quality is best as these are wardrobe staples worth investing in since you’ll wear these over and over again. Leather is a top pick, as it wears nicely and can develop a nice patina. Suede is another great option, but it requires a bit more thought and maintenance to avoid snow and water spots.

Try to avoid cheap or fake leather, as these can crack and look not so good in little time. But if you want to avoid real leather for personal reasons, don’t worry, there are high-quality vegan leathers out there!

Shop for neutral colors first, such as black and brown as those will go with the majority of your outfits. Once you have your classics, feel free to get a fun statement shoe!

I’d also try to avoid a stiletto unless that’s your thing. A block or thick heel is still great for elevating a casual look, plus, they’re easier to walk in!

Madewell, Everlane, Nordstrom, J.Crew, & Sam Edelman all have great shoes ranging in mid to high pricing.

Whether you want a casual look or a polished look, a jean and boot outfit is the best way to achieve both! One of the best things about this outfit is that by switching out your boot style and the kind of jeans you have, you can create so many stylish outfits.

For another style guide on how to wear your basic pieces, keep reading!

Up Next: 5 Blazers To Wear With Jeans for an Easy Yet Put Together Outfit

jeans and boots outfit


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.