Looking good in western boots depends more on the pants you wear than the boots on your feet. A single pair of boots may be adopted to any number of situations, but different types of pants are needed for different social settings. Here is a guide on how to wear men's western boots with different styles of pants.
Shorts: Don't Wear with Boots
Shorts should not be worn with any style of western boot. Addressing women's boot styles, Country Outfitter advises women to look for a dress that falls just above the knee when wearing cowgirl boots. Wearing shorts of a comparable length is not okay for men, though. Women can get away with showing some leg, but people don't want to see a man's hairy kneecap.
If you're headed to a summer picnic where shorts would be acceptable, decide between shorts and boots. You can't wear both to the party.
Jeans: Wear Inside Fancy Boots
Jeans and boots are a classic look, and they can be worn different ways. You may want to wear your jeans inside or outside your boots, depending on your jean's cut and your boots' design.
Jeans are tucked inside fancy boots. Tucking jeans into cowboy boots shows off the boots' pattern. If your boots have a threaded design or are made of a unique material, such as snakeskin or alligator hide, you may want to tuck your pant legs into your boots. Otherwise, no one will be able to appreciate the artistry.
Only certain styles of jeans will fit inside cowboy boots. If you're going to wear jeans inside boots, look for a pair of straight-leg or skinny jeans.
Jeans: Wear Outside Plain Boots
If you have a pair of roper or work boots, which are typically less detailed than cowboy boots, there is no reason to tuck your pant legs into the boots. Since there is little artwork to showcase, you can cover the top of the boots. Regular-cut and boot-cut jeans fit boots nicely.
Khakis: Wear Outside Boots
Khakis can be worth with all types of western boots, including cowboy, roper and work boots. As the quintessential business-casual pant, however, they should never be tucked into a pair of boots, regardless of the boots' style. Doing so would create a shabby, unprofessional look.
Although Khakis are often a shade of brown, they can be worn with any color boot -- including black. Sachin Bhola says that the fashion rule that prohibits wearing brown and black together is dated. He admits that combining the two colors might create a flat look but suggests compensating by mixing up textures. Juxtaposing the cotton of khaki pants with the leather of western boots will ensure your outfit is not flat, even if it does include both brown and black.
Dress Pants: Wear Outside Boots
Like khakis, dress pants should always be worn outside western boots. Your dress pants should be hemmed so that they just touch the floor at your heel. There should be a single crease in the front of each pant leg, about where your ankle is. Tucking dress pants into boots would mess up this hem.
The next time you put on your western boots, think about what type of pants you are wearing. If you're wearing jeans that can be tucked into the boots, consider showing off your fine footwear. If you have any other pair of pants on, though, refrain from tucking the legs in. As long as you follow these guidelines, you'll always look good in boots.
For more info about wearing your boots in style, contact a local retail store that specializes in men's western boots.