15 Stylish Boots to Wear With Jeans: From Skinnies to Flares

Pairing boots with cute jeans can seem like a no-brainer. But with so many styles of jeans, from skinny to wide legs and flares, and endless new styles of boots, it can feel overwhelming to know what goes with what.

Today, I’m sharing some popular combinations that will make it easier for you to decide.  I’ve rounded up some of the newest boots you can pair with jeans, so you’ll look and feel amazing at 40, 50, and beyond!

15 Boots to Wear With Jeans: Skinny, Flare and Everything In-Between

What Boots to Wear with Straight-Leg Jeans

Ankle Boots

Ankle boots are perfect for pairing with straight-leg jeans, and there are so many types available that you can create a wide range of looks. Choosing the right ankle boot for your straight-leg jeans is easy if you think of it this way.

Whether you are wearing regular-length or cropped straight-leg jeans, the denim should hit below your boot shaft. This means that the shaft of your ankle boot needs to be high enough to sit under your jeans or at least meet the hem. There should be no flash of leg showing. Yes, really! Showing a flash of skin used to be in style but is now passé in 2025.  

My favorite ankle boots to wear with straight-leg jeans are kitten heels because they make an outfit look elegant and feminine. These suede kitten-heel ankle boots are classy and modern. The delicate pointy toe complements slim, close-fitting, straight-leg jeans.

Sock Booties

Sock Boots look classy with straight-leg jeans. These stretchy, leg-hugging boots fit snuggly under straight-leg jeans (and even narrower, slim, straight-leg jeans), guaranteeing no flash of leg. I wear often wear sock boots with slim pants, but they work just as well with jeans. Right now i have my eye on this gorgeous brown suede pair. 

Chelsea Boots

There’s a couple of types of Chelsea boots that look good with Straight leg jeans. Block-heeled Chelsea boots  are lower and easier to walk in than sexy, high-heeled booties, but can still look polished. I love these elegant pointed-toe Dolce Vita Chelsea Boots. They’re classy and very comfy, and this reddish-brown color is gorgeous.

Chunky Lug Sole Chelsea boots have a totally different vibe but also look great. They’re more utilitarian. I like this black suede waterproof pair from Blondo. Notice how they are tall enough in the shaft to sit at the hem of my jeans without showing any skin.

Western Boots

Western style boots are is in style right now! The latest Western booties give a nod to the Western look rather than having an “on my way to the rodeo look.”  Look for modern versions of the traditional cowgirl boot with a sleeker design or softer leather. 

What Boots to Wear with Wide-Leg Jeans

Some gals are on the fence about wearing wide-leg jeans because they can make you look a little wide and boxy. But you can look longer and leaner in wide-leg jeans when you know the right shoes to wear with them.

In general, a big, chunky lug sole bootie with a rounded toe worn withwide-leg jeans will weigh you down at your ankles and give you that Frankenstein foot look. You’re better off with ankle boots that have a slim heel and a pointy toe,  or wear Block Heel booties which are a popular choice.  

Ankle Boots with a Block Heel

Ankle boots with a chunkier block heel are fantastic for balancing out a wide-leg pants look. You foot doesn’t look as chunky but you get some height and black heels are easy to walk in.  The key is to find block heels that are sleek-looking and don’t have any extra bulk at the ankle. I own two pairs of these side-zip block-heel ankle boots in brown and black. The heel isn’t too high and they look nice under jeans. If you wear them with ankle jeans there’s no awkward gap between your jeans and boots.

Knee-High Boots

Knee-high boots can also  work with wide-leg jeans. Yes, they’re tall, but they slide easily under wide-leg jeans and they keep you warm in winter. I love these sophisticated faux croc knee high boots. The point toe balances out all that fabric at the hem and the point toe helps give you your pants that long lean flowy look.

Platform Boots

Although not as popular, platform boots can work, too! They’re very practical for gals who want height but don’t feel their balance is very good in heels. These suede platform boots give you height, and are sturdy and dependable. The platform isn’t too heavy looking and the almond toes is more elongating than a round or square toe.

What Boots to Wear with Flare Jeans

Pointed-Toe Boots

Flared Jeans with round-toe booties feel dated, although an almond-toe bootie can work. Pointed-toe boots are more modern and sophisticated and will make your legs look like they go on for miles.

Pointy-toe boots can have many different types of heels. Two of the most flattering with flare jeans are kitten heels or block heels.  These kitten-heel pointed-toe boots are a nice shorter boot option since they’re playful and chic. If you prefer a taller boot, I love these Schutz western pointed-toe heels!  

Western Boots

Another trendy boot that complements flare jeans is modern-style western boots!  Many of these boots have fun stitching and interesting textures, which can add personality to your outfit.

These chunky-heeled cowboy boots are a chic option for pairing with flare jeans! If you want something with more stitching detail, these Abel booties won’t disappoint. 

What Boots to Wear with Ankle Jeans

Ankle Boots

The fun thing about wearing ankle boots with ankle jeans is that you can show off your boots entirely! But remember, you still want to make sure your ankle boots line up with your hemline so you get that seamless look with no skin showing.

Since we get to show off the whole boot, why not wear something fun and eye-catching, like snake-embossed ankle booties? Or even studded boots for a more edgy look?

What Boots to Wear with Baggy Jeans

Chunky Heel Ankle Boots

Chunky heel ankle boots work best with baggy jeans’ oversized and relaxed vibe. The chunky heel offsets the jeans’ wide-leg silhouette and gives them a classic look. Chunky heel ankle boots with a pointy toe are the most flattering and help balance the weight at the bottom of the pants. These pointed-toe block ankle boots have a chunky heel that lifts them and balances the loose fabric of the baggy jeans. 

Combat Boots

If you want to make a rebellious fashion statement, boots like the Dr. Martens you rocked years ago can be worn with baggy jeans, but it’s definitely not a look for everyone. If you don’t want to look like a granny in combat boots, you may want to think more about straight-leg jeans with Chelsea boots.  Fearless fashionistas can try 1460 Pascal boots! Try slightly cuffing your jeans to hit the top of your combat boot for a more defined look.  

What Boots to Wear with Boyfriend Jeans

Heeled Booties

Pairing heeled boots with loose boyfriend jeans elevates the relaxed, laid-back look. A pointed toe elongates the leg and polishes the look, while the heel gives you a boost without making you uncomfortable. This look is perfect for dinner or a polished daytime look!

Chelsea Boots  

Chelsea boots are a timeless, classic option. Their close fit gives them a sleek look that balances out the loose fit of boyfriend jeans that are regular length or cropped. These lug sole low heel Chelsea boots are a good fit with the cool tomboy look of boyfriend jeans.

What Color Boots to Wear with Jeans

We’ve discussed the style of boots to wear with jeans, but what about the color? With basic blue denim, anything goes.

In general, if you want a more conservative formal look, keep your top and boots the same color. For example, you could wear blue jeans, a black sweater, and black boots.

Mix it up for a more casual and modern look. Wear blue jeans with a black sweater and burgundy or dark green booties. Matchy-matchy isn’t wrong; it’s just more of a classic, older look.

What Color Boots to Wear with Black Jeans

Black jeans are a little dressier than blue jeans, which is why I love wearing them in the fall. I like to enhance the sophisticated vibe of black jeans by pairing them with these color boots.

• Black on black is always a solid option. It keeps the look classic, seamless, and sleek. Plus, it is very slimming.
• Brown boots pair wonderfully with black jeans, especially in cognac or chocolate shades. There’s a contrast there, but it isn’t too striking. 
• Burgundy or deep red boots look amazing with black jeans. They add a pop of color without totally overwhelming the outfit. 
• Animal print is another winner when it comes to wearing black jeans. Leopard, Croc, or Snake print is a fun way to add print and personality to a black jeans look!
• Boots with metallic accents can be a daring choice, but a great one, nonetheless! They make a fashion statement without being too bold. 

If you have any recommendations I didn’t mention, let me know in the comments! I would love to add to this list of pairings to tweak your chic!

How do you plan on styling your boots and jeans now?

I’m a big fan of figuring out how to wear boots and jeans in modern ways.  Just check out my advice on how to wear ankle boots with dresses and how to wear skinny flare jeans for some more inspo!  

Aside from that, I hope I was able to help you navigate and figure out exactly which boots and jeans combo works best for you! Every look should make you feel like your most fabulous, age-amazing self. 

Be sure to stay up to date with my LTK storefront. It’s the best way to follow along with my affiliate links and find styles that work for you. Don’t forget to chat with all the other gals in The Fabulous After 40 Dressing Room to compare which jeans and boot style you like the best! Join here!