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Wearing Cowboy Boots

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This is a pictorial description for men on how to wear cowboy boots with jeans for casual wear and with dress clothes for work in an office setting. I wear cowboy boots most every day where I work on the U.S. East Coast in a professional office. I wear them with casual khaki pants, slacks, and dress suits, too. Cowboy boots are comfortable and good-looking. Following are my opinions and come from a perspective of American culture.

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Outside or Inside Jeans?

There seems to be a lot of people who have opinions about wearing jeans inside boots or not. The general day-to-day opinion is that guys wear jeans over boots. While many photos of my cowboy boot collection on my website show me with jeans tucked into the boots, those photos were made to show the boots for purposes of the website. The photos don't really show how I ordinarily wear my boots with pants over.

Some people make snide remarks about the character of guys who wear jeans inside boots. My feeling is, "heck, if you have nice boots and want to show them off, then by all means, do so!" But for ordinary day-to-day wear, jeans over is the way to go with one exception: Buckaroo boots.

Tall Buckaroo boots are made to be worn by cowboys when working on horses on a farm or ranch. The boots are designed to be shown. In this case, tuck your jeans in. Otherwise, don't.

Stacked Jeans

People have asked me what "stacked jeans" really means. What is illustrated in the photos is just that -- the jeans are long enough to come down to the foot of the boot, but not so long as to drag on the floor behind the heel. The jeans may form a soft fold along the foot of the boot. That is "stacked jeans" -- simply, the jeans are long enough to stack (or fold) on top of the boot foot.

Length of Jeans, Slacks, Trousers, or Pants

Your jeans or pants should come down to the foot of the boot, and if necessary, be a little longer to form the "boot stack" fold on the foot. The back of the jeans or pants should not drag on the floor. While to some guys, frayed ends of jeans is a stylistic choice, for most guys, finished hems that meet the back of the heel and top of the foot are preferred.

Note that denim is made of 100% cotton, and cotton shrinks when washed a number of times -- even if washed in cold water. Expect pre-washed (or "pre-shrunk") denim jeans to shrink about 3/4" to 1" (1.9cm to 2.5cm). Having jeans be a little longer at first is preferable to jeans that are shorter, so even when the jeans shrink, they will still stack nicely at the foot of the boot.

Cowboys wear jeans that stack. If jeans cover the shaft of the boot but do not come down to the foot, then the jeans are not the correct fit. Real cowboys call short jeans "high-waders" and other names. In the U.S., jeans that don't stack are considered "goofy" or odd. (Or worse.)

Straight-Leg, Boot Cut, Flare, Bell Bottom?

This is a personal choice, but most guys choose straight-leg or Boot Cut jeans. The differences between these styles is rather minor. When buying jeans, read details on the width of the opening at the foot. Most cowboy boots have a 16" or 16-1/2" circumference. The jeans should be at least as wide as that.

Flare and Bell Bottom Jeans are relics of the 1970s. While jeans with these leg openings may still be available, they are seldom worn except for nostalgic purposes. Real cowboys usually wear straight-legged jeans.

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Color of Jeans

Again, this is a personal choice. Most jeans are from medium to dark blue. It's also common to find men wearing black jeans. There are other colors available: brown, green, khaki, and even white. Most guys in the U.S. wear jeans that are blue or black. Blue jeans go especially well with cognac or tan boots. You may occasionally see men wearing brown or khaki (beige) jeans. Cowboys do not wear jeans in other colors, such as green, red, yellow, or white.

Wranglers, Levis, or designer jeans?

Cowboys, especially those who ride horses, and Bikers (those who ride iron horses), prefer Wranglers because the heavier, "rolled" seam on Wranglers is on the outside of the legs (to reduce rubbing in the saddle) while Levis have the heavier, bulkier seam on the inside of the legs. The seam can rub against the leg while riding a horse or motorcycle. Levis were popular years ago. But since their production was moved outside the U.S. in 1996, the quality is not in the product like it once was. And designer jeans? FuggetAboutIt. Unless you're on a fashion runway, save your money and get Wranglers. Masculine men -- gay or straight -- wear regular-old straight-legged blue jeans. (Don't even ask about how silly baggy and low-rise jeans look on adult men.)

(Photos and some content courtesy of DaveM, used with his permission.)

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Khaki Pants?

Yes, many men wear cowboy boots with khaki (casual) pants both at the workplace and casually. There is no rule that you must only wear denim jeans with cowboy boots. Traditional leather cowboy boots in brown, tan, or cognac look great with tan or straw-colored khaki pants. Black and black cherry boots go well with grey, olive, or blue casual pants. A lot of guys choose to wear khakis with boots on "casual Fridays" or in my case, almost every day since my employer does not have a formal dress code for professionals. More photos of me wearing khakis with boots are here.

Do Men Wear Cowboy Boots with Suits?

Yes, good-looking leather or subdued exotic boots (such as python, ostrich, or cobra in dark colors like black, brown, or black cherry) go fine with a business suit. Many men, particularly in the U.S. Midwest, wear boots with suits regularly. Even though I work in Washington, DC, I wear boots with suits too. (See photos of me in cowboy boots and suits, here or just shirt, tie, and boots, here.)

If you have to (or choose to) wear a suit, ditch the dress shoes that the clones wear and pull on a pair of dress cowboy boots. Just make sure that there is not a company dress code policy that gives specific instructions about footwear. Usually, nobody says anything about seeing boots on your feet, or if they say something, it's complimentary. The only person concerned about it is someone who is insecure about his footwear choices. If you like boots, then wear them. Don't worry about what others may say or think. That is their problem, not yours.

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Boot Fasion Choices

Men are sometimes concerned with fashion considerations, such as the color of boots to wear with certain colors of clothing, particularly for office wear. Such color-matching considerations do not matter when a guy is wearing denim jeans since boots and jeans go well together in any combination. However, the color-matching concerns could be an issue, albeit more of a personal one, with dress clothes.

Regular guys who are secure in themselves and are not obsessive about fashion have found that the color of boots and belt does not matter that much. Some fashion websites say that the boots must match the belt, and generally go "with" the color palette of the clothes -- so brown boots with tan khakis and a brown belt, or black boots with a navy suit and black belt.

However, in the opinion of this regular boot-wearing office-situated professional, the articles you find on men's fashion websites are written primarily by men who are disconnected from reality of what real men wear with boots in an office. Real guys don't give a darn about fashion, but they do not want to draw attention to dramatic differences in their clothing, either. Face it, most guys dress as clones. To reduce the clone-look, get a pair of black leather cowboy boots, pull them on with dress clothing, and step out with confidence!

Many experts on boots recommend that a man have at least two pairs of boots. Give a pair a rest for at least a day before wearing them again. This allows boots to air out and for sweat that absorbed into the leather and footbed to evaporate. If you do that, then consider having one basic black pair of all-leather cowboy boots, and then another color, such as black cherry or brown. Save the exotic skins for a future purchase when you develop more confidence in wearing boots.

If you alternate the pairs of boots you wear, then you should alternate the colors of clothing you wear with them. Blue clothes with black boots on one day, tan/brown clothes with brown boots on the other. These color combinations work. However, it is not against the law and you won't be shot if you wear brown boots with navy slacks or black boots with khaki (wheat-colored) pants. Where what you like--enjoy the freedom of being your own man!

Moral of the story: the internet seems to feature much too much consideration about men's fashion that, in the real world, is immaterial. Seriously, few people, if any, care about what's on your feet and if the colors match your clothes, and no one says anything about it.

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Socks to Wear With Boots

Questions always seem to arise about what kind of socks to wear with boots. Here's the secret: despite marketing recommendations from some vendors, you don't have to spend a fortune to have comfortable, dry feet inside boots.

First-of-all, if you have those thin socks worn with dress shoes, put them away. Those kind of socks wear out quickly when worn with boots. And think about it -- no one can see socks when worn with boots, so the color doesn't matter. Grey or white socks work fine.

Socks come in three lengths: 1) ankle socks, sometimes called sport socks, which some guys wear with sneakers while playing sports or working out at a gym. These socks are not suitable to wear with boots. 2) mid-calf (or crew length) socks are what most men are familiar with. They extend to the middle of the calf and are the most common socks worn by Americans, and are what I wear with boots. It doesn't matter if the socks slide down the leg a little bit, because no one sees socks under boots anyway. (Another good reason not to wear shoes -- you don't have to worry about committing a style faux paus by showing hairy legs.) 3) over the calf (OTC) hosiery, the formal name of what is commonly called "knee socks," are recommended by the style guys to wear with dress shoes. Regular guys (or western wear stores) call them boot socks, but guys wearing boots don't need socks that go up that high on the leg. Really, guys wearing boots do not need to wear boot socks!

Why don't I recommend boot socks? Quality cowboy boots are made with a leather lining so if the socks do not come up as high as the boot shafts, that's okay. The boots should not rub on the legs, and if you have quality socks, they will stay up on your calf all day. You don't need to spend more money for something that you don't need. So what if socks slide down the leg a little bit? Most guys could care less.

You do not have to spend a lot of money for good socks, either. Most variety stores and on-line retailers carry mid-calf socks made of a blend of cotton (for comfort); nylon, rayon, or polyester (called "acrylics" -- to keep shape and stay up); and wool. Yes, wool -- you know, that yarn made from sheep. The best kind of wool is called "Merino," (a kind of sheep), which does not cause itching as some other types of wool. You need wool in socks to wick away sweat. Your feet will feel cooler that way.

You may find socks made of cotton and acrylic blends only, which are not as good as socks that have wool in the blend, since acrylics do not absorb sweat nearly as well. Be wary of inexpensive socks made only of acrylic/cotton fibers. The socks may wear for a long time, due to the durability of the acrylic fibers, but the socks do not breathe, or wick away sweat. When feet get sweaty, they are more likely to get an infection, such as athlete's foot which is caused by a fungus that loves hot, sweaty feet.

Summary: wear crew-length socks made of cotton, wool, and an acrylic blend. You can find at any store that sells men's clothing, including KMart, Sears, Kohls, and similar retailers.

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How to Break In New Boots

Breaking in new boots and what to do before wearing boots for the first time is a common question. Here are ten simple steps:

1. Unpack the boots from the box that they came in carefully. Look them over for any blemishes or damage. Check the insides, too. Look for the size markings in both boots and make sure that is what you ordered. (It is rare, but sometimes boots of different sizes are shipped, or the boots were seconds or damaged in transit.)

2. Reach down inside the boot and remove any wadded up tissue or cardboard spacer that may have been crammed inside the toe of each boot. (Nothing like discovering that the hard way! Ouch!)

3. Keep all of the packing materials inside the box, just in case you have to pack the boots up again to return them.

4. Clean the boot with a lintless soft cloth. Sometimes boots stored for months or years arrive dirty. Apply leather conditioner to boots made of smooth leather. Leather conditioner is much better than paste wax because it keeps the pores of the leather open and helps the boots remain cooler on your feet.

5. If necessary or if you want to, polish or shine the boots using materials recommended by the manufacturer. Paste wax works okay on cow leather, but as stated above, leather conditioner is far better than your Dad's old waxy stuff. Wax polish is not the right choice for exotic skins such as snake, alligator, or ostrich. For those, you should apply exotic leather conditioner instead (search the term to find it and where to buy it either locally or on-line.) Furniture polish works for boots with a plastic top coat -- like All American Patrol Boots, Dehner patrol boot shafts, or Chippewa "Hi-Shine" engineer boots. Use the right product for the right application. (If you are not sure what to use, write to me to ask.)

6. I recommend to break in all boots by hand at first. I created a video "training the ankle of Dehner Boots" (available here). I suggest doing this with all boots, including cowboy boots. Just insert one hand into one boot and use the other hand to bend the back of the boot shaft backwards, so it forms a straight bend where the shaft meets the foot at the ankle. Bend the boot forward and do the same thing. Then bend the boot back and forth until you see gentle creases along the back and the front of the boot. As you walk in the boots, this will be where the boots will crease naturally.

7. Pull on a quality pair of socks made of a blend of cotton, wool, and acrylic fibers. See my section on socks.

8. Pull on your boots. Pull your jeans up, pull on the boot, and then pull the jeans leg down over the boot. Optionally, you can tuck your jeans into your boots (explained here).

9. Most new cowboy boots have a smooth leather sole. Be careful walking on carpet or on rain-slick sidewalks -- it is very easy to slip and fall until the soles develop enough wear to provide traction.

10. Walk around wearing your new boots. Walk on a sidewalk or pavement to help break in the soles. Walk up and down stairs to help break in the foot and the shafts. Just walk in your boots -- about four hours and the boots should be fully broken in (give-or-take, depending on the thickness of the boot, whether it is lined with leather or not, and a few other factors.) Generally, the more stiff a boot feels, the longer it will take to break in.

Stand tall, walk proudly, and remember to smile -- show your confidence as a boot-wearer!

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Do You Have to Wear a Cowboy Hat with Cowboy Boots?

No. In fact, in today's American culture, most men do not wear a hat at all, except if they may be going out in the rain, in which case he may choose to wear a ballcap. The traditional "10-gallon" felt cowboy hats are seldom worn these days except in the rural Southwestern or Western United States when the weather is cold. I like traditional cowboy hats, and may choose to wear one made of straw when I am outdoors in bright sunshine, as the sun can burn my scalp with the little hair I have left. My choice to wear a hat is for personal protection, not for style.

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Leather Jeans and Cowboy Boots?

Some guys like the look of leather jeans and cowboy boots, or chose to wear cowboy boots with leather to mix it up a little. If you do choose to wear cowboy boots with leather jeans, then stack the jeans over the boots (not tuck the leather inside the boots) and wear cowboy boots of the same color as the jeans -- usually black. Anything else makes the boots stand out and draws attention to differences. You want people to look at your face, not be distracted by an odd combination at your feet.

How to Put on Cowboy Boots

Yep, I've been asked that, too. Simply: put on your jeans, then sit down. Lift the fabric of each leg one-at-a-time, and pull on the boot. Pull the fabric of the jeans over the boot. Repeat with the other foot. If the boots have laces that need to be tied, then tie them. Stand up. You're done.

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Jeans Inside Cowboy Boots

As stated above, it is not often that one wears jeans inside cowboy boots, but I have been asked from time to time how to get jeans to stay down inside boots while wearing them. Here's how I do it.

First, pull the jean fabric in the back and bottom of the leg taught. You will wrap the fabric to the side of your ankle. Pulling it from the back and wrapping it from there will keep the seams of the jeans in line with the side seems of the boot, making a neat appearance.

Next, pull your sock up over the top of the end of the jeans.

Push the end of the jeans into the sock.

Pull the sock up over the jeans while continuing to smooth out the jeans into the sock. You want to avoid bulging, but it is alright to have a bulge of the end of the jeans inside the sock because you won't see it once the boots are on your feet.

Repeat with the other foot and sock

Pull your boots on.

Tuck remaining loose pants leg fabric inside the boot.

And there you have it -- jeans inside cowboy boots!

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Note: This page and ALL content including images on this website are protected by Copyright. Read my copyright page here. This page, text or images from this page, or anything from this website may not be downloaded or reproduced/uploaded elsewhere without expressed written permission. Violators or websites/forums where my content is reproduced without permission will be prosecuted to the fullest extent of the law.

More info on cowboy boots--
Eliminating chafing, stretching, shrinking,
squeaking, or sagging, and details on skins

Cowboy Boots and Suits

Cowboy Boots and Khakis

Shirt, Tie, and Boots

Guide on Choosing Different Styles of Boots

Motorcycle Boot Guide

Patrol Boot Guide

Posts about Cowboy Boots on BHD's Blog

Write to me

Cowboy Boots Work Boots Motorcycle Boots Dress Boots
Active Motorcycle Gear

Retired Motorcycle Gear

Fetish Leather Gear