All the Best Boots to Wear with Jeans in 2024 – A Woman’s Guide

As a stylist who loves jeans, I've created many articles about which boots to wear with different jean types. Today, I'm putting all that info into one article!

Jeans are on the top of the trending clothing chain for women in 2024. Looser-fit jeans are trendier now–but don't worry–if you want to wear slimmer jeans, go for it!

With all the types of jeans dominating the concrete, digital and fashion runways, it's a good time to talk about which boots go with jeans.

In Part 1 of this post, I'll outline the 3 best boots for any jeans style: from slim, to baggy, cropped and long!

In Part 2, I'll tell you which specific boots and booties I believe best suited with each jean type. I'll include all your favorites including wide leg jeans, straight leg jeans, flare jeans and more!

This post is written, as always, by Cristina Ehm, your resident ShoeTease fashion stylist with over 20 years experience in the fashion industry!

5 Best Boots to Wear with Jeans – All Styles

The 5 boot styles listed below are shoes that go with everything, including jean types. They're even easier to style when you choose them in neutral shoe colors!

1. Ankle Boots

Although each season they may alter in height or shape, classic ankle boots never go out of style – and look great with all jeans!

Pick ankle boots with a 2-4 inch block heel or stiletto with a pointed toe or slim square toe for maximum versatility. The trendiest ankle boots have a taller shaft, so I'd reach for one of those!

Ankle Boots We Love:

2. Combat Boots

Edgy yet timeless, combat boots come with platforms, higher heels or classic soles. Classic styles, with a Cuban heel block heel and a slight tread can be worn over slimmer jeans, or under straight or wide leg jeans.

For maximum style grit in a trending style, go for a platform combat boot. I adore the Jadons from Dr Martens in particular.

Combat Boots We Love:

3. Chelsea Boots

Chelsea boots are pull-on boots for jeans that look great in fall, winter and even spring. These come in a variety of styles and offer a similar aesthetic to combat boots.

A classic version, such as Blundstones, can look great styled with socks and straight leg jeans or peeking under longer or cropped wider jeans.

Chelsea Boots We Love:

4. Western Boots

Because of their versatile shape, allowing slimmer jeans to be tucked into them, or looser jeans to fall over there, cowboy and western-style boots are easy to style with pretty much any women's jean style.

Great boots for jeans when you're feeling casual and a little yee-haw!

5. Taller Boots

Calf boots are the easiest of taller boots to style, but knee boots can also work great too–especially this season. Since skinny jeans aren't as popular, a current look is folding a fuller let jean, like a straight leg pair into the boots, for a laid-back look.

Knee boots fit well under wide leg, flared and even looser cropped-leg jeans. And of course, they will eternally look fabulous over skinny jeans or jeggings!

Looking for boots to wear with specific jeans styles? Below are 7 of the most popular types of jeans for women, with a roundup of which shoes look best! 

Best Boots to Wear with 7 Jean Styles

1. Boots with Straight Leg Jeans

Straight leg jeans fall down the leg straight from the upper thigh area. And because straight leg jeans are roomier than skinnies, they can accommodate many more shoe and boot styles, especially with wider-width styles.

Do you have straight leg jeans that taper at the ankles? Then those aren't technically straight leg jeans but mom jeans. You can skip to that section here! 

• Combat & Chelsea Boots: You can't beat these edgy styles for casual fall/winter looks, which look extra rugged with a rolled jean hem. 
• Classic Ankle Boots: Roll up the hem to show off your boots, or keep your jeans down over them. If long enough, of course!
• Knee-High Boots: Tuck your straight leg jeans into knee-high boots for a sleek, stylish appearance that's perfect for colder months. Not for the faint of heart, but it can look great if done right!
• Western Boots: both low and high shaft versions work. Tuck them into your boots to show off any interesting detailing. I love a short version of the boots with a rolled-up jean. 

2. Boots to Wear with Wide Leg Jeans

Right now, wide leg jeans are all the rage! They stand in stark contrast to skinny jeans. These jeans come in various styles: baggy, long, or cropped.

Jeans with a broader straight leg also fall into the wide leg category. For more on pairing shoes with these jeans, see the related section!

To get the most flattering look, choose wide leg jeans that fit snugly at the waist, hips, and upper glutes. This will highlight your waist and allow the fabric to flow beautifully below.

Given that wide leg jeans have a broader fit at the calves and ankles, boots with block heels and robust outsoles complement them well, adding balance to your look.

• Cowboy Boots: Choose cropped wide jeans with western ankle boots or a longer style with classic cowboy boots.  
• Combat & Chelsea Boots: With a heel or lug sole, a more rugged Chelsea or combat boot can look edgy, especially if you style the side of the wide hem by tucking it partly into your boot. 
• Knee Boots: with shorter wide leg jeans, knee boots can be a vibe. 
• Classic Ankle Boots: these look great with a bit of a heel and are trendy with a rounded square toe. My preference is to wear these with cropped wide leg jeans!

3. Boots to Wear with Skinny Jeans

Skinny jeans have a snug fit from waist to hem. While some are so form-fitting they might be mistaken for jeggings, others offer more space around the knee and/or ankles. This year, the latter is much more preferable.

The actual fit of the skinny jeans often depends on the design and the individual's calf & ankle size.

There are so many great boots to wear with skinny jeans, no matter how slim they fit. For a general styling guideline, I lean towards boots that are more streamlined, with a slender toe shape and refined heel.

Cropped skinny jeans are perfect for showcasing a unique heel or even ankle boots with intricate details.

Bulkier boots might clash with the sleek profile of skinny jeans, potentially offsetting the overall aesthetic. However, if you have a penchant for a bolder look with your skinnies, the fashion choice is all yours!

Skinny jeans are the easiest to pair with most boots. Especially sleek and slim-fitting boots! They fit seamlessly on top or just at/under your jean hem. 

• Classic Ankle Boots – any shaft height or heel height works with skinnies. Pull the boots over the jeans, or let your ankles show with cropped styles.
• Socks Booties – great, especially with a finer heel and pointed toe for a night out!  
• Combat & Chelsea Boots – any style works. Just keep the heels minimal & sleek. You can even style your boots with wooly or fishnet socks that pop up from above the boots!
• Tall Boots – Knee or over-the-knee height boots worn over the jeans create a sleek silhouette for day or night. 
• Riding Boots – perfect for the lady who prefers a little equestrian prep in her step!

4. Boots with Flare Jeans

Bootcut jeans widen from the knees downward. Flared jeans exhibit a more pronounced flare, bootcut jeans have a minimal flare, while bell bottoms take the flair to an even more exaggerated level.

Given the flared design common to these three jean styles, certain boots pair perfectly with all of them.

With flared or bell bottom jeans, many boots, particularly those that are taller, can easily slide underneath. This includes iconic cowboy boots. Here are the best boots to complement these jean styles:

• Heeled Booties: Wear block heel booties with ankle length flares or longer. Choose a fun stiletto or kitten heel for an above-ankle length flare.
• Cowboy Boots (ankle and mid height): Embrace a classic Western look by pairing your flare jeans with cowboy boots, which easily slide under the flared silhouette.
• Ankle Boots: I love a classic ankle boot that has a mid height block heel with bootcut jeans. You can play around with toe shape, but a rounded square is particularly trendy right now.
• Chelsea Boots: Choose a chunkier fit with a wider flared jean and less of one, for a bootcut.

5. Best Boots with Baggy Jeans

Baggy jeans are big, loose, and cozy. They look good with tough or boho-style boots. It depends on your style!

For high-up baggy jeans, they should fit well at the waist. This makes them look more chic, even if they're loose.

For low-down baggy jeans, they should hug the top part of your waist/hips. If not, they might look too big, like they're not yours, or worse, fall right off!!

1. Ankle Cowboy Boots: Ankle height cowboy boots look cool with long, or ankle baggy jeans and tucked in or out. 
2. Ankle Boots: Opt for ankle boots to create a balanced and fashionable outfit, tucking in the hem of your jeans if desired. Best with slightly tapered styles. 
3. Combat & Chelsea Boots: Achieve a cool, edgy look by pairing your baggy jeans with combat boots emphasizing the laid-back style.

6. Best Boots to Wear with Cropped Jeans

There are so many types of cropped jeans! These can be wide-legged & loose, skinny or straight-legged. In any form, they will hit right above the ankles or higher. 

Cropped jeans give room to show off fun detailing such as a fun heel. Lug soles or chunkier style boots balance out wider leg cropped jeans, while slim cropped jeans often look best with a more streamlined– aka less chunky–boot with a finer heel.

• Sock Booties: These look great with a stiletto heel under straight leg or slim jeans, while a more block heel.
• Chelsea Boots: Love a higher shaft Chelsea boot that hides under a cropped jean hem.
• Combat Boots: These in a taller also look fun, but regular height combat boots are also great!
• Calf Boots: These work perfectly under a straight or wider cropped jean, showing off more of the boot! You can also tuck yours slimmer jeans into them.
• Western Boots: These look so fun with cropped jeans. Opt for a lower boot with a wider leg or taller cowboy boots with cropped straight leg jeans.

7. Best Boots with Mom Jeans

Today's mom jeans fit better than the baggy ones from the 1980s and 90s. They can look good with many boots!

Mom jeans now sit high on the waist and have a comfy fit in the leg. Some are straight, and some get a bit narrower at the bottom. Here, we'll talk about boots for the narrower fit.

You can roll up mom jeans or leave them down. Either way, they match with lots of boots!

• Kitten Heel Booties: These really refine the look of mom jeans and fab in ankle boot or sock boot format.
• Western Boots: Love a great cowboy boot tucked into a mom jean, for a laid-back, yet stylish style.
• Calf or Knee Boots: Tuck mom jeans into boots or wear a wider leg version right on top.
• Combat or Chelsea Boots: I love the look of cuffed mom jeans with a more rugged boot!

Let's Recap: Boots to Wear with Jeans

If you've come to this point, kudos! You now have the knowledge to pair boots with jeans across various styles, fits, and lengths!

As we've explored, crafting a memorable look with jeans goes beyond the denim itself. It hinges on pairing them with the perfect boots.

Jeans are a wardrobe wonder item to their adaptability! Figuring out how to coordinate boots with jeans ups their style quotient.

From laid-back ankle boots to elegant knee-highs, your choice of boots can wholly revamp your outfit, bringing a unique touch to various jean styles.

Whether it's a classic straight leg, a vintage-flavored flared cut, or an evergreen straight legged jean, there's a perfect boot (or boots!) waiting to round off your outfit.

So, let your boots and jeans be the showstoppers, and always remember: confidence is your most captivating complement. Dress in what brings you joy.

Need more shoe and jean pairing ideas? Check out my post all about the best shoes to wear with jeans (that don't include boots!).

xo ShoeTease

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