Someone used an internet search on “rules on wearing cowboy boots” (and ended up on the cowboy boot section of my website). Someone else asked, “what guidance can you provide when I wear cowboy boots? Are there rules?”

I’m not sure why there seems to be an interest in “rules.” There aren’t any rules, per se, about wearing cowboy boots, but here are some suggestions based on my experience.

Rules for wearing cowboy boots

1. Wear what you like and what fits you and your lifestyle.

2. Stand tall and proudly.

3. Smile! Men appear more confident and self-assured when they smile (and wear boots!)

4. Stop obsessing about what other people may say or think about you wearing cowboy boots. Seriously, get over it. If you’re worried that someone may say something because wearing boots is new to you or not common where you live, then make the choice not to wear them. But it is YOUR choice — not someone else’s.

5. If you have nice boots that you want to show, tuck your jeans into them. If you don’t want to do that, then don’t. It’s your choice.

6. Cowboy boots go well with dress clothes or a suit. Generally, it is wise to choose an all-leather boot or subtle alternate skin boots (such as smooth ostrich or Teju lizard) in black, brown, or black cherry and which have a rounded or semi-rounded toe and traditional heel height. Boots with more fanciful design, sharp X-toes, high heels, or made of unusual materials (Caiman alligator, rattlesnake, python, etc.) may be too ostentatious to wear to places where one might wear a suit, such as at an office, conference, wedding, funeral, or to a place of worship.

7. Have at least two, if not more, pairs of cowboy boots if you will be wearing them regularly. It is a good idea to let boots “breathe” for at least one day between wearing them. The boots need to air out and allow time for sweat which may have been absorbed into the leather and insole to evaporate. (This is also sometimes called “rotating boots” but does not mean turning them around.)

8. IMHO, do not wear cowboy boots that have smooth leather soles while operating a motorcycle. This is a safety precaution — smooth soles provide no traction! Same applies about wearing smooth-soled cowboy boots in places that may be slick with rain, snow or ice.

Keep your boots clean and in good condition

9. Mud will dry out leather. While sometimes it’s fun to get boots muddy, it is also important to clean it off when you’re done playing so the leather is not permanently damaged.

10. If boots somehow get biological stains on them, wipe it off — don’t let it dry on. The most often-applied biological agent that somehow gets on boots dries out leather and may cause permanent damage.

11. Avoid getting boots that are made of snakeskin or lizard wet. Scales on snakeskin boots will curl when they get wet, and they will not “uncurl” when they dry.

12. Use a quality leather conditioner or reptile skin conditioner on your boots. Avoid using waxy shoe polish on boots (or parts of boots) that are made of materials other than leather — snake, lizard, alligator, etc. Waxy shoe polish can build up within the scales or fine creavases on boots and dull the finish or ruin the skin.

13. Do not use a hair dryer on boots, put them in an oven, or place them near a source of heat such as a radiator or forced-air heat vent. That can cause leather or skins to shrink permanently. If boots are wet and you want to hasten the drying process, a trick I learned from Bamaboy is to put the boots on top of a water heater.

14. Store boots so air can circulate around them. Keep them in a well-ventilated area. Keep them in the light — avoid storing boots in dark, damp places. That includes storing boots in a box when the boots may be wet. Mold and mildew love “dark and wet”. They “eat” fibrous products, and particularly have a “taste” for leather. To avoid having boots be destroyed by mold and mildew, keep them dry, in the light, and in a place where air circulates.

Life is short: stand tall, walk confidently, and smile while wearing your cowboy boots!

The following searches were done recently, and all ended up on my Jeans and Cowboy Boots page on my website. It continues to amaze me that at least 200 people visit my web page about jeans and cowboy boots every single day.

Information about cowboy boots (and jeans) is searched much more often than I thought. I will refrain from speculating why — other than to say that searching on the Internet is done so often now, rather than asking someone in person. It is faster, easier, and gives you a choice of answers to pick from (whether right or wrong, good or bad.)

Here goes — I have divided the searches by categories as indicated. Note: these were searches done by people in the United States and Canada. One might figure that people outside the U.S. & Canada who are unfamiliar with cowboy boots and customs may have more questions, so I did not include non-U.S./Canadian search results on this list.)

Jeans and Cowboy Boots

• Jeans men wear with cowboy boots
• What is stacked jeans?
• Do you have to have boot cut jeans with boots?
• Best jeans for cowboy boots
• Do cowboys iron their jeans?

Responses (my opinions): most guys choose to wear Wrangler jeans with cowboy boots. Wranglers have the thick rolled seam on the outside, instead of the inside, of the leg. Cowboys and bikers choose jeans with the rolled seam on the outside so it doesn’t rub against the leg pressed against the saddle of a horse or motorcycle (thought I do NOT recommend wearing cowboy boots with leather soles when operating a motorbike.)

Most men choose straight-leg jeans to wear with boots. Boot Cut jeans have a slightly flared (wider) leg opening, but this isn’t necessary. It is mostly a marketing ploy designed to get you to pay more for the cut of the jeans, rather than get any improved functionality from them. And no, most guys (cowboys or not) do not iron their jeans. Just wash and dry and that’s it.

Stacked jeans means, simply, that the jeans are long enough to rest with soft folds (“stack”) on top of the boot foot, but not be so long as to be lower than the top of the heel (or fray by dragging on the floor).

Wearing Cowboy Boots

• How to wear cowboy boots
• How to put on cowboy boots

Responses: I am puzzled why someone would search “how to wear cowboy boots.” Ummm… pull them on, stand up, walk. What else is there to know? Stand and stride confidently, held held high? Be proud? Smile? Then the question, “how to put on cowboy boots” — that’s easy. Sit down, pull up the leg of your jeans, and pull the boots on. Repeat with the other leg. You’re done.

Jeans Inside Boots

If there is anything that people obsess over more about cowboy boots and jeans is the ongoing question about wearing jeans inside boots — or not. Here is what was searched:

• Can men wear their jeans inside their boots?
• Do guys tuck pants into boots?
• Why do cowboys tuck their jeans into their boots?
• What does it mean when pants are tucked into cowboy boots?
• Men with their pants inside the boot

Responses (my opinions): Yes, men can and sometimes do wear jeans inside boots. It doesn’t “mean” anything about the person who does it, yet others seem to be afraid of what other people may think. My observations (here in the United States) are that most men wear jeans over cowboy boots, except boots like Buckaroos, which are more often worn with jeans inside them than over them. Overall, my opinion is that if you have nice boots and want to show them off, then tuck your jeans into them. If you obsess about what other people may think of you doing that, then forget the boots and wear sneakers. Life is too short to worry about other people’s opinions, and you will arrive at this conclusion with time and maturity.

Why do cowboys tuck their jeans into boots? It comes from an old tradition of doing that since the Roman and Greek times, mostly to protect the lower leg with stronger, more firmer protection of the leather on the boot shaft. Doing so also makes it easier to keep the jeans clean and not be exposed to dirt, mud, and gunk that may fly up from a horse’s hooves.

Other Unusual and Amusing Cowboy Boot Related Searches

Here are some other searches related to cowboy boots that I saw come in:

• Rules for wearing cowboy boots
• How to wear tall boots with jeans men
• What boots do real cowboys wear?
• Should I wear cowboy boots?
• Wear jeans over cowboy

Responses (my opinions): The only “rules” for wearing cowboy boots are: 1) wear what fits you and your lifestyle best; 2) stand tall, walk confidently, and remember to smile! That’s it — simple as that!

How to wear tall boots with jeans? I think this may be going back to some of what was above about wearing jeans and boots, or wearing jeans inside boots. “How” to do it? Use this trick: sit down, and pull the sock on your left leg up over the end of your jeans. Pull the jeans down to smooth them, and make sure the inside and outside seams of your jeans run down both sides of your legs. Repeat with your right leg. Then pull on your boots. Smooth the jeans into the boots to reduce puckering of the jeans fabric at the top of the boot shaft. Stand up, stand tall, walk proudly. Smile!

What boots do “real” cowboys wear? Good question. Most working ranchers and riders may wear solid, sturdy boots like Buckaroos while actually riding a horse and working with cattle. When the go to town, you will often see them in ropers, which have a short shaft and rounded toe. The traditional, 13″ cowboy boot with fancier stitching and design is worn more for dressy occasions, and by some men in the U.S. Midwest, South, plains & mountain states, and Southwest, to work (even with a suit.) I have observed that a rounded toe or squared toe is more common than a pointed toe, but that is a matter of personal preference and varies widely.

If you have to ask, “should I wear cowboy boots,” then you probably shouldn’t. You’re obsessing too much. Let go, relax, and wear your boots, but don’t fret over whether you should or shouldn’t. It is a personal decision, made by YOU, not the opinions of other people around you.

I close with a final funny: wear jeans over cowboy. Yeah, I know what happened here, but it still amuses me by conjuring up some pretty ridiculous images in my mind. I will leave it to your imagination. (giggle)

Life is short: wear your cowboy boots!

Okay, loyal blog readers, it’s time for another poll!

I am seriously considering getting one or both pairs of cowboy boots featured here. What do you think? Vote in the poll to the right and let me know. Thanks.

Pair 1: “Silvercreek” boot from Nocona® features a full quill ostrich leather foot and 13″ fancy stitched leather shaft. Leather lining. Supportive, handpegged steel shank. Pointed toe. Color: denim.

Pair 2: Justin “Bent Rail” buckaroo boot features a buckskin bay Apache leather foot under a fancy stitched 15″ sea blue cowhide leather shaft. Buckskin bay Apache scalloped, punched collar. Easy-on pull holes. Soft leather lining. Leather covered cushion insole and triple density insole board. 1 3/4″ heel. (Click on the image to see it larger).

Update: the poll I took from blog viewers closed on December 9. The results? 4 voted that I buy the Justin Bent Rail buckaroos; 11 voted that I buy the Nocona denim ostrich boots (plus one positive comment about them); 5 voted that I buy both pairs; and 1 voted that I buy neither pair. Majority rules! The blue ostrich boots have been ordered and are scheduled to arrive in January. (January??? yeah, January, 2010.)

I am always amazed at the huge number of visitors to my website’s page on “Wearing Cowboy Boots” who find it by entering phrases like “how to wear cowboy boots” or “do you wear jeans inside or outside of cowboy boots” or “how to you wear jeans with cowboy boots” into a search engine.

Now, to be honest, most guys wear jeans over boots. Jeans are worn “stacked,” meaning the jeans are long enough to fold softly across the foot and across the back of the boot, but not lower than the heel. More information and instructions are on my “Wearing Cowboy Boots” page.

However, if you have nice boots, you could consider wearing jeans inside them from time to time. My pictographic “jeans and cowboy boots” tutorial is visited at least 1,000 times each week. In observing the high frequency of these visits, I decided to update it by showing a simpler method of how to hold the jeans down inside cowboy boots. Come visit the page and see … it’s simple.

Life is short: wear your boots!

This photos shows the sculpture outside the meeting room where I led my sessions yesterday. Man, they must have known that I was coming. How appropriate!

I wore my cowboy boots, as usual, throughout the day and several others wore their boots, as well. We felt right at home.

Welcome once again to Arizona!