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How to Wear Ankle Boots with Jeans

I’m obsessed with ankle boots and jeans; it’s a great look that can take us from a busy day of errands to a casual night out, but getting the style just right can be a bit tricky. So, here’s a quick guide to rocking this look with confidence.

ankle boots with jeans - woman in the city
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The Do’s of Ankle Boots and Jeans

  1. Cuff Your Jeans: If your jeans are on the longer side, cuff them. This small roll or turn-up at the hem can make a world of difference. It shows off the boot and creates a neat, put-together look.
  2. Choose the Right Jeans: Skinny jeans are a natural choice for ankle boots because they tuck in easily. But don’t shy away from straight-leg or slightly flared jeans, either. They can look equally chic if styled correctly.
  3. Play with Colors and Textures: Ankle boots come in so many varieties – leather, suede, bright colors, prints… you name it. Pairing a textured boot with simple jeans can really make your outfit pop.
  4. Mind the Boot Shaft Height: The height of your ankle boots matters. Ideally, there should be a little bit of your leg or ankle showing between the boot and your jeans. This gap is key to a flattering look.
  5. Experiment with Different Styles: From rugged, chunky boots to sleek, pointed-toe designs, there’s a lot to play with. Change up your look according to your mood or the occasion.

The Don’ts of Ankle Boots and Jeans

  1. Avoid Baggy Jeans: Oversized, baggy jeans can overwhelm ankle boots and make the outfit look messy. Stick to fitted styles for a cleaner look.
  2. Don’t Hide the Boots: If you’ve got a fabulous pair of boots, show them off! Avoid jeans that are so long they cover the boots completely.
  3. Be Careful with Boot and Jean Colors: While contrasting colors can be fun, avoid combinations that cut off your leg line in an unflattering way. For example, black boots with light blue jeans can create a stark contrast that shortens your legs.
  4. Don’t Forget About Proportion: If you’re wearing chunky boots, balance the look with fitted jeans. Similarly, sleek boots can pair well with a slightly looser jean style.
  5. Avoid Rolling Jeans Too High: A small cuff or roll is great, but rolling your jeans up too high can look a bit off. Aim for just a couple of inches above your boots.
ankle boots with jeans - skinny jeans and boots

If This Jean Style, Then That Ankle Boot Style

Skinny Jeans

Inseam Length: Just above the ankle or full-length

Boot Style: Any ankle boot works!

For a sleek look, choose a boot that fits snugly around the ankle.

For a casual look – Slouchy or chunky boots add a fun contrast.

ankle boots with jeans cropped jeans and boots

Straight-Leg Jeans

Inseam Length: Cropped or full-length

Boot Style:

Cropped Jeans – Go for a boot with a little height or a standout design to show off.

Full-Length Jeans – Choose sleek, close-fitting boots that the jeans can fall over comfortably.

ankle boots with jeans rolled jeans and black boots

Boyfriend Jeans

Inseam Length: Cropped or rolled up to the ankle

Boot Style:

Chunkier boots balance the loose fit of the jeans.

Flat and low-heeled boots keep the look relaxed and casual.

ankle boots with jeans - boot cut jeans and boots

Bootcut Jeans

Inseam Length: Full-length, slightly brushing the ground

Boot Style:

Opt for pointed-toe boots to peek out stylishly.

Avoid chunky or overly detailed boots as they can get lost under the flare.

ankle boots with jeans - flair jeans and boots

Flared Jeans

Inseam Length: Full-length, covering most of the boot

Boot Style:

Choose boots with a bit of heel to elevate the flare and keep the jeans from dragging.

Slim-profile boots work best to avoid bulk under the flare.


Deciding whether to tuck your jeans into your ankle boots or not is another important part of getting this look right. Here’s a breakdown to help you out:

Tucking Jeans into Ankle Boots

When to Tuck: Tucking works best with skinny jeans because they fit snugly around your legs and won’t bunch up. This creates a sleek, streamlined look that’s especially good with taller ankle boots.

How to Tuck: The key is to avoid any bulky gathering at the ankle. Make sure your jeans are tucked smoothly into your boots. If you find they’re bunching up, try wearing a pair of socks over your jeans to hold them in place.

Leaving Jeans Over Ankle Boots

When to Leave Over: If you’re wearing straight-leg or boyfriend jeans, it’s often best to leave them uncuffed and over your boots. This can create a laid-back, effortlessly cool vibe.

How to Style: If your jeans are a bit longer, let them fall naturally over the boots. Just ensure they’re not dragging on the ground. For a cleaner look, you can give them a small cuff so they sit just above or on the boot.

Half-Tuck Trick

Sometimes, neither tucking nor leaving your jeans over the boots feels quite right. In this case, try the half-tuck. This is where you slightly tuck the front part of your jeans into the boots while leaving the back part out. It’s a stylish, edgy look that works well with looser jean styles.

To Sum Up

  • Skinny Jeans: Tuck them in for a neat, polished look.
  • Straight-Leg/Boyfriend Jeans: Leave them over the boots for a relaxed style. Consider a small cuff if they’re too long.
  • Half-Tuck: A cool option for a more fashion-forward, edgy look.

The right choice depends on the style of your jeans, the type of boots you’re wearing, and what feels most comfortable and stylish to you.


Styling full-length bootcut jeans with ankle boots can be a bit tricky, but when done right, it’s a fabulous look. Here’s how you can nail this combination:

Understanding Bootcut Jeans

First, let’s understand bootcut jeans. They’re designed to have a slight flare at the bottom, which was originally meant to fit over boots. This slight flare can be a great match for ankle boots, creating a balanced and stylish look.

Choosing the Right Ankle Boots with Jeans

  • Low Heel or Flat Ankle Boots: These are a great match for bootcut jeans. They keep the look casual and are super comfortable for everyday wear.
  • Pointed Toe Boots: These can give an illusion of length and work well with the flare of the bootcut jeans.
  • Avoid Overly Chunky Boots: Since bootcut jeans already have a bit of width at the bottom, pairing them with chunky boots can make the bottom half look too heavy.

How to Style Them

  1. Length of Jeans: Make sure your jeans are the right length. They should just graze the ground or sit slightly above it. Jeans that are too long will drag on the floor, while too short ones will disrupt the line of the bootcut.
  2. Show a Hint of the Boot: Let the hem of your jeans fall smoothly over the boots, but it’s nice to show just a bit of the boot – maybe just the toe peeking out. This creates a cohesive look.
  3. Balance Your Top: Since bootcut jeans and ankle boots give a slight flare at the bottom, balance it with a fitted top or a tailored jacket. This creates a nice silhouette.
  4. Color Coordination: Consider the color of your boots and jeans. Darker jeans with darker boots can elongate your legs, while contrasting colors can be a bold fashion statement.
  5. Accessorize: Add a belt or a stylish bag to tie the whole look together.

ankle boots with jeans - woman on the street with black jeans and black ankle boots and a black and white blouse

Pulling off ankle boots with jeans is not just about following trends; it’s about finding what feels good and looks great on you. Whether it’s the snug fit of skinny jeans tucked into your favorite boots, the laid-back air of straight-leg jeans resting on the tops of your boots, or the playful flare of bootcut jeans, there’s a style that fits every one of us.

Final Thoughts on Wearing Ankle Boots with Jeans

  • Pick the Jeans That Work for You: Each style of jeans brings its own flair when paired with ankle boots.
  • Pay Attention to How You Pair Them: Whether you cuff, tuck, or let your jeans fall naturally over your boots can change up your look.
  • Get the Balance Right: The colors and fit of your jeans and boots can really make your outfit pop.
  • Make It Your Own: Fashion is personal. Don’t be scared to mix it up and find what speaks to your style.
  • Stay Comfortable: The best outfit is one that you feel great in.

Up next, Best Winter Outfits for Moms.

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Hi! I'm Jen, and I'm thrilled you stopped by!

I am a certified life coach, mother of five, wife, founder of the non-profit Eye on Vision Foundation, entrepreneur, Christian, and friend. I live, play, work and worship in the Orlando, Florida area.

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