tan ankle boots and socks

12 Best Tips: How to Wear Socks with Ankle Boots

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You bought a pair of ankle boots and you’re excited to wear them! But you’re not sure if you should wear socks with them. 

You may be wondering:

  • What type of socks should you wear with ankle boots and tall boots?
  • What color socks should you wear with your ankle boots?
  • Is it ok for socks to show with ankle boots?
  • How do you wear long socks with ankle boots?

I’ve got the answers to all your questions! First, let’s look at the types of socks to wear with ankle boots and tall boots. 

What type of socks should you wear with boots and ankle boots?

To choose the right socks, first we have to talk about the different shaft heights on boots. 

Measure the shaft up the back of the boot from the top of the heel to the top of the boot.

There are 3 general shaft heights for ankle boots. Low, medium and high. Ankle booties have the lowest shaft at 3 inches. Medium shaft ankle boots stop just above the ankle around 5 inches. And high shaft boots stop about an inch or more above the ankle. Tall boots stop just below the knee. 

Let’s talk about the different types of socks to choose for each shaft height. 

Tip 1: Wear low shaft ankle booties with no show socks.

No show socks are a great choice since they cover the bottom of your foot but are cut very low. They won’t show if you’re wearing a very short bootie or one with side cutouts. 

black no show socks

They come up over the bottom of your feet and just cover the sides of your feet, similar to the nylon footies you wear to try on shoes at the store. The right pair of socks will have a rubber sticky line on the back of the heel that helps the sock stay securely in place. There’s nothing worse than wearing socks that slip off the back of your heel when you walk, so choose a pair that stays securely in place.

I bought these no-show socks at Old Navy. But you can also find similar pairs on Amazon.


Here I’m wearing them with tan ankle booties with a cutout under the ankle.

ankle booties

You don’t see the socks at all. When you need to wear a sock with an ankle bootie that is cut low and reveals the ankle, they’re an excellent choice.

You’ll find that they’re a great option with other shoes in your closet too, like ballet flats, loafers and fashion sneakers.

These no show socks work whether you’re wearing skinny jeans or straight jeans. If you’re wondering how to wear ankle boots with skinny jeans, this post will help. Or with straight jeans, this post will help.

No show socks are also great with pants, leggings or skirts.

Now, what if you have a pair of ankle boots that hit higher up on the ankle? Wear crew socks.

Tip 2: Wear crew socks with medium shaft ankle boots.

Crew socks come up above the ankle by a few inches. They’re the best socks to wear with short boots because they don’t have a ton of excess fabric that will create bulk at your ankles. 

Here’s a picture of a gray marled pair that I bought in a five pack of socks from Amazon.

gray crew socks

These socks are a good choice because they’re soft and are a wool, cotton and polyester blend that’s perfect for everyday wear. 


Crew socks will stick out of the top of your ankle boots by about a half-inch or so. 

Here I’m wearing my tan ankle boots from J.Crew Factory with the same pair of gray and white marled crew socks from Amazon.

tan ankle boots with crew socks

They stick out of the top of the ankle boot by less than an inch.  

Tip 3: Wear trouser socks with high shaft ankle boots.

My tallest ankle boots have a shaft of almost 6 inches. And hug the leg. Higher shaft boots will fit snug because they stop higher up on the leg. A trouser sock is a good choice because they’re thin.

brown ankle boots with brown socks

Your highest shaft ankle boots aren’t likely to show if you wear them with pants. They’ll be tucked under the hem. 

Here I’m wearing them with a slim pair of brown trouser socks that I stole from my husband’s sock drawer. Since they’re longer socks, I scrunched them down at the top of the boot. Since they’re thinner, they don’t create bulky elephant ankles when you push them down. 

Tip 4: Wear tall boots with knee socks.

Wear tall boots with socks that pull up to the knee. And pair a dark sock with a dark boot. Here I’m wearing brown trouser socks that match and blend with these brown taller boots.

brown riding boots with brown trouser socks

Trouser socks end below the knee and may be opaque or sheer. They’re also a great option with tall black leather boots. If you want to wear socks with tall boots rather than tights and stay even warmer, choose a thicker pair. Or add a long coat over top your outfit. 

If you still have boot socks with buttons or lace at the hem. Or some that are extra long and meant to be folded over the top of your boot, consider swapping out those kind of socks for a more updated look.

If you’re looking for thick socks that are very warm, merino wool is a great alternative to pure wool socks to keep your feet warmer. It’s the softest wool that wicks moisture, and is odor resistant. 

When choosing your sock color, you have several options. Let’s go through them.

What color socks should you wear?

Socks are a great way to express your personal style and to be yourself! But if you’re looking for some guidance about how to wear neutral socks with your ankle boots, here are 5 ways to do that.

Tip 5: Choose a sock that matches your ankle boots.

Pick a pair of socks that match your ankle boots so the socks blend and take a back seat to the boot. 

Here I’m wearing brown marled socks with brown ankle boots. 

brown Chelsea boots with brown crew socks

The brown socks aren’t an exact match for the brown color of the boot. But they still do a good job of blending with the boots. 

Tip 6: Choose a sock that matches your jeans or pants.

Select socks that match your jeans, pants or skirt, to visually connect your boots to your bottoms. 

Here I’m wearing a navy and black marled crew sock that came in that Amazon 5 pack.

brown Chelsea boots with navy marled socks

Wearing a sock that matches your jeans, pants or skirt color creates a pattern that makes sense to the eye. And visually connects the pants and shoes.

Tip 7: Choose a sock that matches an element of your outfit like your sweater.

Go for socks that match one piece of your outfit to accentuate that color. Most often, I wear a pair of socks that matches my sweater or top in some way. 

Here I’m wearing tan socks that match my tan cable-knit sweater. 

tan boots and tan sweater

Matching your socks to your sweater creates a visual pattern that makes your outfit more interesting. 

Tip 8: Choose a sock that matches an accent color on your boot.

These platform Chelsea boots have a tan accent line around the top of the lug sole. 

Black platform Chelsea boots with tan socks

I’m matching my socks and sweater to that color to play it up and add some visual interest to the outfit. 

Tip 9: Choose black socks to match black bottoms in your outfit.

Black socks are a good option if you are wearing black jeans, pants or a skirt. 

brown Chelsea boots with black crew socks

Here I’m wearing black jeans with black socks and brown ankle boots. 

Certainly you can wear black short boots with black jeans or pants. But pairing brown and black is very chic these days. Brown boots worn with black jeans makes a statement in a minimalist basic outfit. And wearing black socks is an easy way to tie in the brown boots with the black jeans. 

Tip 10: Choose a sock with a fun contrasting stripe. 

I love cute socks with stripes or bold colors to add some visual interest to an outfit and for a fun peekaboo moment.

These brown duck boots create a casual look and are perfect for cold weather. I’m wearing thicker socks with a contrasting gray body and a double red stripe at the top. 

brown duck boots with gray socks with red stripes

To connect these gray cozy socks to the outfit a bit more, I’d like this even better with a dark gray sweater on top.

Is it ok for socks to show with ankle boots?

Yes, it is a stylish option for your socks to show with your ankle boots. And that’s true whether you’re wearing your ankle boots with jeans, pants, skirts or dresses. Choose crew socks that come above the ankle by a few inches. And let the sock peek out the top of the boot. You can pick a sock that matches the boot color, your jeans, pants or skirt, or an element of your outfit like your sweater, or an accent color on your boots. If you want your socks to fade into your outfit, choose a pair of socks that match your boot color or your jeans, pants or skirt. If you want your socks to make a statement, choose some with a pop of color or a stripe. 

What socks should you wear with sock boots?

Sock boots are a special case. They are slim fitting boots that are made of stretchy fabric that clings to the ankle like a sock. The stretchy shaft may extend several inches up, stopping below the calf. It’s like a boot and sock in one. 

The beauty of these boots is that they’re perfect for wearing underneath tapered straight jeans that have a narrow opening at the ankle. Or with wide-leg cropped jeans. It’s ideal to wear a sock with them to wick moisture away from your feet and keep your feet warm.

Tip 11: Choose socks that won’t show with the sock boots.

Like no-show socks or thin tight crew socks. Make sure the crew socks stay up well inside the boot because you won’t have easy access to pull them up if they fall down. 

How do you wear long socks with ankle boots?

Tip 12: Choose long socks that are thinner.

Long socks are trickier to wear with ankle boots. If you need to wear them, scrunch them down at the top of the boot. Thinner socks will add less visual weight to your ankles when you push them down. If your socks are too thick, you’ll end up with thick blocky elephant ankles.

When picking what type of sock to wear with ankle boots, the perfect socks are the socks that you love and that offer the warmth you need, while looking stylish! Experiment and have fun with it! XO, Marya


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Hi, Friend. I'm Marya. I'm so glad you're here!

I’m here to help women feel good inside and out through approachable everyday style inspiration and encouragement for midlife. Once upon a time, I worked as a therapist and coach. Now, I’m a holistic style blogger studying style coaching! Be So You celebrates leaning into who we were meant to be! 

Read about my  journey to self-discovery at 40. Follow me on Instagram here and Pinterest here. Send me a quick question through my contact page here.  

Fit Note: I’m midsized at 5’6″, 160 pounds, with size 12 jeans.

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