how to wear ankle boots with jeans

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Do you have a pair of ankle boots that you’re not sure how to style? Check out these 15 stylish ways to wear those ankle boots with jeans!

It’s fall or winter. You took out your favorite pair of boots and want to them wear them with your jeans and but with every pair of jeans you pick out, you don’t know, but it ends up looking weird, or something’s off.

If this is your situation, you have no idea how many times I’ve ditched the ankle jeans and boots look just because I was not feeling the vibe. It was when I learned all this over the years that I could finally figure out a way. It’s not difficult, but not the easiest as well.

So let’s quickly get those jeans and booties working for you! There are some tips to style them and 15 outfit ideas that would actually get all the jaws to drop on the street and flood you with compliments! Wooohoo!

Different types of ankle boots that go with jeans

When it comes to getting dressed up for the day, matching your jeans with ankle boots is always a real fashion “win” – not only is it comfortable and chic, but it’s also easy to pull off! Whether you’re looking for something classic or modern, there are plenty of options out there.

If you want an effortlessly stylish combo, opt for a pair of sleek black Chelsea boots. Alternatively, if you want to add a bit of funkiness to your outfit, try some heeled cowboy boots in a bold animal print.

For those who like their style edgy, look for combat boots with unexpected details such as studs and lace-up fronts. Finally, if you’re into something timeless and sophisticated, invest in a pair of pointed-toe suede or leather ankle boots. You know they’ll go with most of your jeans and will last years of fashion choices.

Now that styles are out of the way, there are 3 shafts of boot style also available in the market. High shaft, medium, and short shaft. A shaft is just the measurement of the boot from the top of the heel to the top of the boot. The basic rule of thumb is that when you are tucking in the jeans, you’d generally want to tuck them in tall shaft boots, and when you are wearing cropped jeans, you’d want to wear short booties with jeans.

What kind of jeans go best with ankle boots?

Honestly, ankle boots are one of the easiest to style with jeans. There are just so many types. You just need to find the perfect jeans for you and know certain tricks to wear them right.

1. skinny jeans, obviously

I mean, was there even a doubt? Skinny jeans and ankle boots are a classic pairing. Not only are they comfortable to wear, but the possibilities for style and expression with this combination are practically endless. Whether you’re going for a timeless preppy look or something edgy and street-style, there’s no wrong choice!

How to wear skinny with short boots?

To create an even more polished vibe, try tucking your skinny jeans into the boots and pairing them with a tailored top for a chic dinner outfit. Now there are a few fashion rules to follow while tucking your jeans with ankle boots, which we’ll go over in a second.

For those off-duty days, opt for some high-rise jeggings with shorter ankle boots and complete the ensemble with an oversized blazer – it’ll make you feel like a million bucks! Don’t be afraid to have fun with colors as well – try one of this season’s trending shades, like mauve or beige to really knock it out of the park. Trust me when I say that this fashionable combo is worth the fashion risk!

Do jeans go inside or outside ankle boots?

When it comes to tucking jeans, I have a few rules of my own. Now you can do whatever you like, but this is what I love.

• First of all, skinny jeans always go inside tall shaft ankle boots. I just don’t like how showing some ankle can give an illusion of shorter height to my 5 feet 7 inches ass. I could use anything to help me elongate my legs. To do this, you have to keep in mind to pair darker jeans with darker boots and lighter with neutral color boots. It gives a very cohesive and polished look. For instance, I’d wear dark wash jeans with black boots and white or light wash jeans with beige boots.
• But if you are playing with cropped jeans, make sure your jeans are cut at the same length as your boots for a streamlined feel. If they are longer, you could always cuff them up or fold them under.
• For cuffing, you can either do a single cuff that is big enough to show 1-2cm of skin over the boots or two cuffs.
• “Less is more” – If your jeans are too baggy, you’ll end up creating an unflattering extra bulk that brings your whole outfit down. To avoid this, consider going with straight-leg or skinny-fit jeans so the fabric won’t bunch up under the boot.

2. straight leg jeans

I have a different kind of love for straight-leg jeans. They are stylish, make me look taller and slimmer, and don’t even get me started on how comfortable they are, especially in summer, spring, winter, and fall.

Ankle boots’ sleek designs and higher shaft lengths play beautifully with the fit of straight-leg jeans. In fact, it is one of the best shoes to wear with straight jeans. The slightly relaxed leg over the top of the boot is my favorite way of styling ankle boots and jeans for an uncluttered look. Or you could simply cuff them for an edgy, casual look.

I like to just let the jean be over the boots for a laid-back, clean vibe.

As an extra bonus, playing around with how you style them keeps your ensemble looking fresh AF and keeps the haters asking, “Where’d ya get that?” That’s right—they’ll be wondering while they work their way back down to Earth from Mount Fashionista!

Bottom line: Straight-leg jeans and ankle boots = one sartorial power couple made in heaven.

3. wide leg jeans

What did you say? Comfortable and sexy in one picture? Wide-leg jeans and ankle boots are a definitive combo that can help you create a show-stopping street style. Plus, the variety of textures and colors in this pairing allows you to express your personality while still looking polished.

To really make this look pop, try wearing a low-heel ankle boot in an unexpected cut or woven texture with a subtle wedge or stacked heel to give some extra oomph to your height. And forget the rules about no skin showing between the hem of your jeans and the top of the boots – if it looks cute, then why not rock it?!

Also, since wide-leg jeans have an inherently bold silhouette and wider leg opening, they’ll go beautifully for the times you wanna leave your jeans over your boots, especially when the jeans are longer or cuff-off when paired with a stiletto heel.

Wide-leg jeans are super flattering and versatile, so go ahead and don’t be scared to step outside the fashion box for this timeless yet modern fit. With some confidence (and ankle boots!), you’re sure to bring down the house in this chic look.

4. flare jeans

Okay, so you won’t hear much about this combo, but if you are a pear-shaped body type (smaller breasts as compared to wider hip), flared jeans might be your new haven. They are hotter than ever, look so sexy, and give you the perfect balance and body proportions to look like a hot mama!

Flared jeans are hotter than ever, and if you’re looking for a way to spice up your wardrobe, why not team them up with some ankle boots? With the right style choices, you can create an outfit that looks chic, classy, and timeless all at the same time.

For a more modern look, opt for slim-fit Flared jeans paired with sleek black ankle boots—it’s a combo that’ll have you looking like the cat who got the cream! If you want to add some edge to your look, try distressed denim with statement snakeskin booties—a surefire way to turn heads when you walk down the street.

Whatever route you decide to go down, make sure your jeans are just slightly above the ground and over your ankle boots.

Ultimately, pairing booties with flared jeans is an easy way to get fashionable oomph into any outfit! So don’t be afraid to push fashion boundaries every now and then—you never know when a daring look will become your new signature style.

5. Mom jeans

When it comes to pulling off the perfect mom jean look, ankle boots are the icing on the cake. Not only do they give your outfit an extra edge, but they also help to balance out the added bulk of wearing higher-waisted jeans.

For a classic style, try pairing your mom jeans with brown ankle boots (leather or suede). If you’re looking for something funkier, go for a pair with metallic accents or detailing like embroidery or fringe. Add in a colorful top to help liven up your look, and you’ve got an ensemble worthy of showing off on Instagram!

And don’t forget – by choosing a pointy-toe ankle boot like cowboy boots, booties, or oxfords, you’ll not only nail the trend, but you’ll also elongate those legs of yours and have everyone asking, ‘Where did she get those shoes?!’ Now that’s the confidence we can all get behind!

6. cropped jeans

And if you have doubt that nothing will work for you, you have not yet tried cropped jeans with ankle boots, especially when they are frayed from the hem. They are literally the easiest to style and will make you look chic within minutes.

No doubt they’re easy to pull off no matter your age or personal style, making them the go-to pairing for days when you want to look a little extra trendy yet comfortable.

To ace this classic look, start with high-waisted cropped jeans that hit right at the ankles, as they add length to your legs and make your shoes the main focus. Then pair them with sleek ankle boots in neutral tones, such as black or tan.

To give the outfit a more lived-in vibe, cuff up your jeans, and don’t be afraid to experiment with different textures like frayed bottoms or leather (adding texture to an outfit can instantly make you look stylish AF). For an unexpected pop of color, add colorful socks in bright prints to color block—the bolder, the better!

For the cooler months, layer on a blazer over the top for added warmth without sacrificing style. With just the right mix of cool items from your wardrobe and a few simple accessory touches here and there, you’ll be rocking crop jeans and ankle boots like a pro!

How do you wear ankle heel boots with jeans?

There’s nothing you’d do differently. The only thing that matters while styling ankle heel boots and jeans are the right style of jeans and the color of boots. These boots will go best with skinny, straight-leg, and cropped jeans. And if the jeans are longer, wear the same color boots as your jeans and either tuck the jeans inside or cuff them above to show a little ankle (1-1.5 cm) to give a bit of skin area to the fit.

ankle boots with jeans outfit ideas

1. denim on denim

One of my favorite outfits of all time; I can’t get enough denim-on-denim fits. They are freakin’ easy to put together and look such a bombshell.

2. corset and blazer

Let’s turn those heads and make them wwwoooowww with this corset and oversized blazer fit. You could tuck your jeans into your booties for a messy street-style vibe or just cuff them neatly.

3. graphic t-shirt

And if you don’t wanna use so much brain, just throw a graphic t-shirt over skinny jeans and pair ankle boots to give an edge to the outfit.

4. color blocking fit

Try color blocking only if you want to be known as the known Fashionista of B-town! Don’t tell me I didn’t warn you 😉

5. turtle neck

If you’re looking for an effortless fall outfit, you have to pair your turtle necks this year. Look at the cuffed jeans and ankle boots, giving a rich, sleek look!

6. high-neck sweater

Black and brown boots are wardrobe essentials, but if you wanna add an extraordinary flair to your ankle boots and jeans outfits, you need to get white ankle boots ASAP.

7. t-shirt and blazer

You know how I said I love a little frayed hem action over my boots? This shows why!!!

8. trench coat

First of all, can we take a moment to acknowledge how these patent boots are the star of the outfit? I mean, it’s a gorgeous shirt and coat ensemble you can wear to wear and still stay stylish.

9. pop of color

Oh gosh, this is exactly my kind of streetwear. So stunning, and don’t you love the pop of red (I am all for it)? It’s just an effortless, head-turning look. You could recreate this with any bright colors.

10. tube top and leather blazer

And when it comes to adding interesting elements to the look, leather knows how to do that.

11. white high-neck and denim jacket

If in doubt, always choose black and white. I would generally not tuck different color bottoms inside my boots, but I love it here since the texture of the clothing is the same – leather, and it looks cohesive and hot.

12. leather jacket

If you ask me, a leather jacket over a turtle neck and leather boots is one of my most loved ensembles. What is there not to like? It’s easy, looks polished, and gives a model off-duty vibe.

13. fuzzy cardigan

Since I am a pear-shaped body type, when I say I am obsessed with flared jeans, I mean OBSESSED. And this cute ankle boots and jeans moment has my heart.

14. aviator jacket

You need just one aviator jacket to drop all the jaws on the street. And if it’s in a hot color like red, you know you’ve got the stage all to yourself to set the fire.

15. oversized sweater

There’s something about oversized sweaters and fall that I wanna stay in them all day long. And if you see how beautifully she rocked neutral boots with the same toned sweater.

Concluding how to wear ankle boots with jeans

And that’s a wrap, ladies! The do’s and don’ts of wearing ankle boots with jeans. I hope this was helpful and that you feel armed and ready to take on the world (or at least your closet) with confidence.

If you have any additional questions, leave them in the comments below, and I’ll be happy to answer them. As always, thank you for reading; you guys are the best!