When Do I Wear Tall Boots?

Wescomorrison23I appreciate the blog suggestion from a loyal reader from Belgium. He recently wrote to me to ask,

I was wondering when you wear your knee high boots? Is it always functional, like when riding your Harley? And is it always with the pants tucked in?

This is a great question, and thanks for the blog idea. My answer follows after the jump…

Cops04Like this loyal blog reader, I usually choose to wear tall boots when I ride my motorcycle. This preference for wearing and showing my tall boots originated with my admiration of motorcops in uniform with tall Dehner or similar patrol boots. Yes, dating back to my teens, and when the popular television show “CHiPS” was on air in America, tall boots on a cop captured my attention.

There was something striking about those boots and the man in them — the image of rugged masculinity and an air of confidence and strength — when I knew deep down that even though I admired the appearance, I would never be that guy.

rp_Searseng2.jpgThen when I bought my first motorcycle, I also bought my first pair of tall engineer boots. Made by Chippewa, my “Sears Engineers” portrayed the “rugged bad boy” image of the tough biker. Well, even if I were a wimp in biker’s clothing, I could dress that way.

I soon realized two things whilst wearing my tall engineer boots with jeans tucked in:

1) Those boots protected my legs from rocks, dirt, and water that would fly up from the front tire and spray onto the boots. My clothes would remain (relatively) clean while the boots took on an even more rugged appearance.

2) From all the glances, I saw that other guys admired the boots. Few would say anything, but I could tell — they were feeling like I felt when I saw other guys in tall boots.

rp_Chipnonsteel07.jpgAs I continued to ride and get new and bigger motorcycles, my collection of tall biker boots grew. In my 20s and early 30s, 99% of the time when I rode my motorcycle, I would choose tall engineer boots and tuck my jeans into them. I quickly became comfortable and confident to wear tall boots with jeans tucked in almost everywhere (outside of my work setting at the office), and even when I was not using the motorcycle for transportation.

Was I concerned about what other people would think or say? Yes, at first. But over time, so many of my family and friends would see me dressed that way, they never said a thing. Living in a suburban area where so many people do not know each other, strangers may glance, but no one said anything about the boots either. I learned that any concern or fear about what people might say was unfounded.

Dehnerlug01Then in by my mid-30s, I realized that even us civilians could buy and wear tall police motorcycle boots like Dehners and find cop breeches to go with them. I was emerging into a man who wore boots and breeches like the men I fantasized about in my youth.

Also as I worked with real motorcops as a civilian volunteer, I learned that cop breeches are not worn just because they make a man look sexy. They indeed are functional. Breeches are durable, stretch easily when swinging my leg over the saddle of my motorcycle, are easy to clean, and due to the tapered legs, breeches are designed specifically to fit well inside boots. So this was part of my tall boot-wearing lesson — choose clothing designed to accommodate tall boots.

blufformal09Also, as part of my life-changing and coming out experience as a gay man in my 30s, I got into BLUF (Boots, Leather, Uniform Fan) leather gear, and enjoyed emergence with my spouse (then partner) at a few gay leathermen’s events and activities. There, I would always wear tall boots with my fetish leathers or replica uniforms, which is de rigueur.

As I continued to mature and am now in my late 50s, and while I always choose to wear boots (never dorky dress shoes, sneakers, or flip-flops), I find that I more regularly wear my pants, trousers, or jeans over my boots instead of tucked inside them, for these reasons:

1) Most of my weekday time is at the office where the “businessman clone look” is expected. I still shun wearing suits, but most of the time, I wear a shirt & tie — and dress cowboy boots. Wearing boots with my pants tucked into them just wouldn’t work. Even I — an avowed lifetime Bootman — would think such an appearance would be foolish.

Chipfire2022) I discovered Chippewa Firefighter Boots about 10 years ago and learned how much better these shorter tactical boots felt when I wore them on long motorcycle rides, especially on rides that went to a destination that involved a lot of walking. Those boots are about the most rugged yet good-looking and comfortable motorcycle boots I have ever owned.

rp_Bama4.jpg3) As I have gotten older, I find it more and more difficult to wear heavy, bulky, tall boots like Wescos. I like the appearance of tall Wesco boots, but not how they exhaust me when dragging my feet around in them. There is nothing wrong with Wesco boots — it is only that as I have aged, I am more fatigued with the exertion required to lift 10 pounds (4.5kg) with each step.

4) I have tried and just don’t like tall cowboy boots like Buckaroo boots. Those boots have higher heels, and I cannot wear high-heeled boots without tripping. (I am naturally quite the klutz and have always been quite awkward.) I may have worn tall cowboy boots way back in my youth when I rode horses on the family ranch, but those days are long gone.

bluejeans105) This is minor, but some of my favorite every-day leather jeans that I wear often in Autumn, Winter, and Spring when it is cold, are made of thick cowhide and do not fit inside tall boots without puckering and appear to be ill-fitting. As I have aged, my lower legs have lost muscle tone. That loss of muscle tone means that my lower legs are a bit wider than they used to be. Add thick leather with tall boots of average calf circumference, and the legs feel squeezed and eventually become painful. So nowadays when I wear leather jeans, they are worn over boots (even full leather over boots instead of inside them.

Summary: I like to wear tall boots. I think nothing of wearing tall boots when out in public (outside of work.) I wear them often with clothing that fits well with them, and not always whilst riding my motorcycle. I don’t care what other people may say because my experience is that other people seldom say anything about the boots except one thing: “hey man, cool boots!”

Life is short: be comfortable in your booted appearance and wear them proudly with confidence.