Wearing Socks With Cowboy Boots - Best Style Guide for 2021

How to Wear Socks with Cowboy Boots and Join the Yeehaw Club

Cowboy boots are the fashion shoe you didn’t know you needed, and they’re very “now”. With Old Town Road dominating the summer charts and no end to the remixes in sight, artists like Lil Nas X are reintroducing country to the mainstream. It’s safe to say country is having a pop culture moment. 

Cowboy boots tend to conjure up images of rough and rugged ranchers or farmhands spending their days herding cattle and squinting up at the unrelenting sun. The whole cowboy look is part of the aesthetic of old westerns with not a lot of full-blown crossover into mainstream fashion. For born and bred city slickers, it’s hard to wear a head-to-toe cowboy outfit without it looking like a costume. 

From which type of cowboy boots to choose to what socks to wear with cowboy boots, the journey to making the country look work for you can be a real humdinger of a pickle. Enter the urban cowboy. This look blends city sensibilities with country classics, the most notable being the cowboy boot (western hat optional). These boots can be dressed up or down, and with the right swagger and confidence, you can create a look that really stands out

If you’re looking to add a little western vibe to your style repertoire, read on. This article will help you choose the right cowboy boots to fit your personal style. We’ll also talk about what socks to wear with cowboy boots so you’re not caught out here slippin’

Choosing the Right Cowboy Boots

So you’ve been thinking about getting yourself a pair of cowboy boots, but aren’t sure where to start. Before you decide what kind of socks to wear with cowboy boots, you’ll want to decide which boots suit you best. Each has a unique profile designed with both functionality and fashion in mind. These are some of the most current styles:

The Traditional Western Boot

This is the classic cowboy boot. The shaft of the boot is typically about 12 inches, making it fairly tall. 

The Work Boot

This boot is designed for durability and comfort with a lower, wider heel and rubber sole. If you’re on your feet for most of the day, this boot is for you. 

The Shortie Boot

Think of this as the classic western boot’s kid brother. The boot shaft runs between 6 and 10 inches, making it the shortest of cowboy boots. 

The Riding Boot

Riding boots are instantly recognizable with their height and heels. They don’t look like typical cowboy boots, but they are certainly built for riding. They are as ubiquitous in the English countryside as they are on an American cattle ranch. 

The Buckaroo Boot

This is the boot for when you’re feeling fancy. With a boot shaft height of around 14 to 16 inches and ornate stitching, buckaroo boots are made for getting attention, especially as a rodeo rider. 

When to Wear Cowboy Boots

Knowing when to wear cowboy boots can feel tricky. Their distinct look instantly says something about your personality and sense of style. While it’s always good to make your mark, you also want to make sure your footwear choice is appropriate, depending on the occasion. It’s also good to keep the weather in mind if you’re planning on keeping it country for all four seasons. 


Did you know that cowboy boots can be worn all year round? It will really come down to choosing what socks to wear with cowboy boots. Choosing socks made of moisture-wicking fabric is a must. In weather extremes like summer or winter, wool socks are best. You’ll also want to make sure your boots have good treads to keep you upright on any icy patches. 


Type & Length of Sock


Knee high or crew socks


Knee high or crew socks


Knee high wool socks


Knee high wool socks


If you’re truly committed to country style, you’ll be happy to learn that cowboy boots can be dressed up or down. Wear them as part of a streetwear look or even to a more casual wedding. What will make the difference as far as whether your look is casual or formal will be the style and condition of the boots you choose. 

Scuffed cowboy boots that look loved and lived-in are fine for day trips, when running errands, or at a country club or festival. Choose a nice, newer-looking pair for dressy casual events or dates. For semi-formal events, try the shortie, which can be worn with boot cut trousers or slim-fitting trousers for a more modern look. 

Breaking Them In: Wearing Cowboy Boots 

Snug-fitting leather shoes and boots are far from forgiving when you first start to wear them. Cowboy boots are no exception. There are a number of issues you may encounter on your way to getting your boots to actually feel comfortable. Also, choose boots that are made with top-quality leather with no rough patches on the inside. You may want to invest in toe and heel pads as well. These tips should help you to survive the break-in period:


Blisters when wearing new boots are fairly common. They’re also fairly awful. Make sure to wear socks with cowboy boots to ensure a comfortable fit. We'll get into what socks to wear with cowboy boots right after this. 

Sore Feet

Proper arch support will help to lessen or eliminate foot pain. Grab yourself a good pair of insoles if your boots are lacking.


If you’re unused to boots with a significant heel, your first pair of cowboy boots may be a fall hazard. Practice wearing your boots at home, or try a pair or western workboots with a lower, wider heel. It’s also good to choose boots with a rubber sole that has traction if you’ll be wearing them in wet, snowy, or icy conditions.

Pinched Toes

Boots giving your toes the squeeze? Most cowboy boots have a narrow toebox. Try going up half a size for more wiggle room.

Best Socks to Wear with Cowboy Boots

So you’ve looked at your options and chosen the perfect pair of cowpie crushers. Now, what are you going to put in them (besides your feet)? Choosing what socks to wear with cowboy boots can make all the difference in terms of all-day comfort. No, your favourite pair of well-worn crew socks with holes in the heels won’t do here. In general, the best socks to wear with cowboy boots are breathable and moisture-wicking. Depending on the height of the boots and your personal preference, choose between:

Casual Socks

When figuring out what socks to wear with cowboy boots, casual ones are a good bet. Hitting at mid-calf, they’re the perfect height for all-around comfort, especially if you’re wearing your pant legs over your boots. 

Knee High Socks

What socks to wear with cowboy boots that are of the riding or buckaroo varieties are knee highs. These socks will hit just below the knee, helping to protect your skin from chafing on your boots. 

Wool Socks

Believe it or not, Merino wool socks will keep your feet warm in the winter and cool during the summer. If cowboy boots are a wardrobe essential, wool socks should be as well. 

By all means, when you're choosing what socks to wear with boots, any type of sock can work. Consider the chart below a guide for the best socks for each boot type. 

Type of Boot

Casual Socks

Knee High Socks

Wool Socks

Traditional Western

Western Work boot





The Best Socks for Sweaty Feet

Warm feet in a pair of warm leather boots is the perfect combo for too much moisture. Sweaty feet are more than just uncomfortable. Over time, sweaty feet can go from being a small inconvenience to a legitimate health issue with conditions like:

  • Odor
  • Athlete’s foot
  • Toenail fungus

Luckily, there are a number of things you can do, including making sure you have the best socks for sweaty feet on hand. Wool socks, in particular, can help draw moisture away from your feet. Here are three steps you can take to mitigate the moisture problem:

  1. Wash your feet thoroughly with antibacterial soap
  2. Once your feet are fully dry, apply foot powder or cornstarch 
  3. Wear breathable, moisture-wicking socks

Best Western: Build Your Outfit Around Your Cowboy Boots

Still worried about your cowboy boots and accessories looking like a costume? That’s actually something to be embraced! The modern cowboy look is all about cool confidence.

There’s no blending in with this distinct style. That doesn’t mean you can’t choose a few pieces here and there to make the look a little less Rancho Relaxo and a lot more Rodeo Drive. After you've chosen what socks to wear with cowboy boots, take a few key pieces to throw together an outfitjust don’t wear them all at once:

  • Western-style shirt: chambray, contrast piping, plaid
  • Leather belt with statement buckle
  • Boot cut or slim-fit jeans
  • Leather, suede, or jean jacket 
  • Accents like a bandana or a vest

Do You Wear Socks with Cowboy Boots?

The answer is a resounding yes. There may be a few “no”s, but chances are they’re too busy nursing their blisters to speak up. Choosing what socks to wear with cowboy boots is fairly easy, with casual socks as everyday staples and wool socks saving the day during hot summers and cold winters. If you’re going for knee high buckaroos, grab a pair or two of knee high socks. Then, put together a winning western ensemble, get out there, and turn heads.