Wearing Cowboy Boots

Length of Jeans

Your jeans 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 should not drag on the floor. While to some guys, frayed ends of jeans is a stylistic choice, for most cowboys, 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.

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.

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 bluejeans with cowboy boots. Traditional leather cowboy boots in brown, tan, or cognac look great with tan or straw-colored khaki pants. A lot of guys make this choice on "casual Fridays" or in my case, almost every day since dressing up is not required where I work unless we have a meeting with people from outside the company.

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 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. The color combinations work. However, it is not against the law and you won't be shot if you wear brown boots with navy slacks. This combo looks just fine.

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.

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.

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.