How to Wear Ankle Boots with Jeans: The Ultimate Fashion Trend Showdown

I only recommend products I love and I think you will, too. If you click on links I provide, I may receive a little compensation. Learn more.

It’s fall or winter and you’re itching to wear your favorite boots with your jeans. But no matter which pair of jeans you try, something just doesn’t feel right.

Trust me, I’ve been there countless times, ditching the ankle jeans and boots combo because it just didn’t vibe with me.

I’ve learned a thing or two over the years and now I’m here to help you unlock the secret to rocking this look. It’s not the easiest task, but with a little guidance, you can make it work like a pro.

So let’s waste no time and dive right into it! I’ve got some killer styling tips and 15 ankle boots and jeans outfit ideas that will turn heads and have everyone talking.

Get ready to strut your stuff and soak up all the compliments. We’re about to slay the fashion game, and it’s gonna be epic. Wooohoo!

What to consider when pairing ankle boots with jeans?

Noooo babe, you cannot simply decide to wear the boots you have with the jeans you have. You need to see what style of shoes you have and what shaft length it is. Then, you’ll decide on how to style them for a winning outfit!

What all styles of ankle boots are out there?

For a sleek and effortlessly stylish look, go for classic black Chelsea boots. Or, if you’re feeling bold and funky, try some heeled cowboy boots in a fun animal print.

If edgy is your vibe, combat boots with studs and lace-up fronts will give your outfit the perfect edge.

And if you’re all about timeless sophistication, invest in some pointed-toe suede or leather ankle boots. They’ll go with any pair of jeans and last you for years of fabulous fashion choices.

Okay, so there are shafts too. And they’re important!!

There are three boot shaft styles to choose from: high, medium, and short. The shaft is just the height of the boot from the top of the heel to the top of the boot.

But why are they important? Here’s the deal: If you’re tucking in your jeans, go for tall-shaft boots. They’ll give you that sleek, tucked-in look. And if you’re rocking cropped jeans, short-shaft booties are the way to go.

Do jeans go inside or outside ankle boots?

Let’s talk about the best way to wear jeans with different types of shoes. Now, you can do whatever you want, but I’ve got some rules that I think work best.

1. Skinny jeans always go inside

First of all, skinny jeans always go inside tall shaft ankle boots. I personally don’t like how showing some ankle can make me look shorter, so I always tuck in my skinny jeans. What can I say, I love looking even taller!

To lengthen those legs, keep in mind that darker jeans work best with darker boots, while lighter jeans pair well with neutral-colored boots. It’s all about that coordinated and put-together look. Think dark wash jeans with black boots and white or light wash jeans with beige boots.

2. Cropped jeans always stay out

If you’re rocking cropped jeans, make sure they’re the same length as your boots for a sleek vibe. If they’re longer, you can cuff them up or fold them under to make it work.

Speaking of cuffing, you can go for a single cuff that shows off a bit of skin (prolly 1-2 cm) over the boots, or try two cuffs for a stylish twist.

3. Pointed toe or not, that matters too!

If you’re wearing a shoe with a pointed toe, then it’s best to have a slight break at the hem of your jeans. On the other hand, if your ankle boots have a round or square toe, then wearing cropped jeans or rolling up the hem works perfectly.

4. Ditch baggy jeans for Straight or wide-leg

If your jeans are toooo baggy and long, you’ll end up creating an unflattering extra bulk near your boots that will bring 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.

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 and boots, obviously

No doubt about it, skinny jeans and ankle boots are a match made in fashion heaven. Not only are they super comfy, but the style possibilities are endless!

Whether you want a timeless preppy look or something edgy and street-style, you can’t go wrong.

How to wear ankle boots with skinny jeans?

Well, for a polished vibe, tuck your jeans into the tall-shaft boots and pair them with a tailored top for a chic dinner outfit.

But if you’re going for casual streetwear attire or have short booties in hand, make sure the jeans hit just above your ankles, leaving a bit of skin showing between the hem of your jeans and your boots.

On your off-duty days, go for high-rise jeggings with ankle boots and throw on an oversized blazer. Girl, you’ll feel like a million bucks!

2. straight leg jeans

I’m obsessed with straight-leg jeans! They are stylish, make you look taller and slimmer, and don’t even get me started on how comfortable they are, especially in summer, spring, winter, and fall, lol.

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 straight from the runway.

Personally, I like to let the jeans just hang over the boots for a laid-back, clean look.

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 frame? Wide-leg jeans and ankle boots are a definitive combo that can help you create a show-stopping street style.

So when styling wide-leg jeans with booties, you don’t have to do anything fancy with your jeans – just throw on a pair of ankle boots and let the jeans sit on them effortlessly! No rolling, tucking, or cropping necessary.

But what if your wide-leg jeans are naturally cropped? No worries, gorgeous. Just opt for taller ankle boots instead of shorter ones. You don’t want to show too much skin between your jeans and booties when the bulkiness of the jeans is doing all the talking!

4. Flare jeans

Okay, so you won’t hear much about this combo, but if you are a pear-shaped or inverted triangle body type, 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!

Now, about styling ankle boots with flared jeans – NEVER tuck them in your boots. You may or may not cuff them, your choice. I usually give it a cuff or two if the jeans are way too long, but that’s it!

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

Also, with flared jeans, make sure you wear pointed or sharp boots rather than rounded ones. The former will stand out better, and the latter will hide.

5. Mom jeans

Not only do ankle boots add that extra edge to your ensemble, but they also help balance out the bulkiness of those higher-waisted jeans. Talk about a win-win!

Now, Mom jeans are typically cropped or end above the ankles, so the best way of wearing ankle boots with them is to leave a little gap between the two.

If you’re a fan of classic vibes, pair your mom jeans with some brown ankle boots in either leather or suede. Looking to spice things up? Opt for ankle boots with metallic accents, cool embroidery, or even fringe. You’ll be turning heads left and right!

6. cropped jeans

If you haven’t tried rocking cropped jeans with ankle boots, you’re missing out on the easiest and chicest style hack out there.

No matter your age or personal style, these babies are a guaranteed win. They’re perfect for those days when you want to look both trendy and comfy – a total fashion double whammy.

To master this timeless look, start with some high-waisted cropped jeans that hit right at your ankles. They’ll elongate your legs and put all the attention on your fabulous footwear. Pair them up with some sleek ankle boots in classic shades like black or tan.

To add a little extra flair to your outfit, roll up those jeans and play around with different textures like frayed hems or leather. Trust me, a little texture can instantly up your style game. And don’t be afraid to go bold with some colorful socks for a fun pop of color – the louder, the better!

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.

Now, let’s feast on these gorg ankle boots with jeans outfits!

1. denim on denim

One of my favorite outfits of all time; I can’t get enough denim-on-denim fits. They are SO 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 styling 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!

Related articles to how to wear ankle boots with jeans

• 16 Gorgeous Dresses To Wear With Thigh-High Boots
• 31 Super Cute Winter Outfits That Are To Die For (Not Kidding!)
• What To Wear To A Pumpkin Patch? 21 Cutest Outfits You’ve GOT To See!
• How To Dress If You Are A Petite Busty Woman Without Holding Back

how to wear boots with jeans