A good friend of mine recently asked me, “Do you have a very very favorite pair of boots (cowboy or otherwise)? Like, the “bury me in these” boots?”

He said that it would be really hard for him to make a choice, and the same is true for me. I can’t say that I have one particular pair of boots that are my absolutely favorites, but here are some of my top choices.

Bury me in…

This may be surprising to some of you, but bury me in my Chippewa Harness Boots. I want to go out as a biker. No suit, no dress boots. Leather jeans, jacket, and traditional, common, ordinary-every-day biker boots. (Actually, I will be cremated, not buried, but that’s a different story.)

Marry me in…

Lots of things ran through my mind while getting dressed on the morning that I was married. Unlike women are known to do, I did not obsess over the choice of footwear, but I gave thought to what boots I should wear. I was wearing a suit, though that choice was more last-minute. I was going to wear leather jeans, but my spouse talked me out of it. He wanted to wear a suit and wanted me to wear the same. Okay.

I have lots of dressy cowboy boots, but knowing that I am a wee shorter than my spouse, yet I wanted to look him directly in the eye when I said my marriage vows, I decided to wear my Legendary Cowboy Boots.

My spouse bought me those expensive custom cowboy boots and the boots have a higher-than-usual heel, so when I stood straight up, I was on direct eye-level with my spouse during the marriage ceremony. So now you know the real story about why I selected that pair of boots to wear when I married.

Escape from a fire in…

When my friend asked this question, he also asked “if your house were on fire and you had time to take only one pair of boots with you, what pair would it be?”

My answer is simple: whatever was on my feet (or bare feet if I were in bed at the time). I have a strong fire safety background and am a life member of my local fire department. No delay in escape. Just crawl low under smoke and get out! Boots are replaceable. I am not.

Fortunately, I had the foresight to have automatic residential fire sprinklers installed in our house when I built it. If there were a fire, one sprinkler in the room of fire origin would douse the fire while my spouse and I escaped, called the fire department, and they arrived for mop-up duty.

Ride all day in…

I love to ride my Harley, and on those rare occasions when I can take a long, long ride with my club, I choose boots that are comfortable, durable, and easy-on-the-feet — especially if there is walking involved at the destination. My choice? My favorite-of-all motorcycle boots, Chippewa Firefighter boots. Really, honestly and truly, the very best in comfort, design, and utility for a motorcycle boot.

These boots are easy to put on and take off (once you get the initial lacing of the boot zipper right). They are lightweight, and serve in-a-pinch as comfortable boots to walk and stand in for a long time — such as at a biker event or show. With a quick spray of furniture polish and a lintless cloth, it is easy to restore a brilliant shine. I could go on and on about how much I really like these boots, but I have already done that.

Wear breeches with…

I like to wear breeches (leather or otherwise) when I ride my Harley. I do not wear them all the time, but when I do, my favorite pair of boots to wear with breeches are All American Blue Knight patrol boots. Yep, great boots for breeches. Of course, I default to Dehner patrol boots, too, which also look great and work well with breeches, too.

Wear leather with…

Hmmm… hard to say. Leather jeans over the boots? Then I probably choose Chippewa firefighters again. They look good, rugged, and masculine. They also keep a great shine with little fuss.

Leather tucked into boots? Then I like to wear lug-soled Chippewa Hi-Shine engineer boots. These boots have a calf circumference to accommodate the thickness of leather tucked into them. The boots are also very comfortable to wear (standing at a bar, for example), and are easy to maintain and keep shiny.

Cowboy up in…

Now this is really really tough. Honestly, I do not have an ultimately favorite pair of cowboy boots. I have some really nice custom and top-of-the-line commercial boots, as well as a number of general run-of-the-mill comfy classics. I wear cowboy boots every day to the office (on days when I cannot ride my Harley due to weather), and frequently wear kickin’-back comfy cowboy boots when knockin’ around the neighborhood. I cannot answer this question. OMBIT, give me one demerit.

Do yard work, home repairs, and snow duty in…

Again, hard to say, but I do not have nearly as many pairs of work boots as I have other styles. But when it comes to work boots, I have three favorite pairs, depending on what I am doing.

Timberland classics when doing yard work. Very comfy.

Chippewa Arroyos Cowboy/Work boots when using my Harley to ride to a work site. Damn comfy boots with a great Vibram sole and heavy enough to withstand the gaff, but light enough to be comfortable to wear all day long.

Chippewa loggers to wear in cold, snowy, wet, or muddy conditions. Very comfortable boots that keep my feet warm and dry.

Summary

How does a man who has over 200 pairs of boots make a choice of his “favorite boots?”

Answer — he doesn’t.

Life is short: wear boots. Lots of boots. Always.