I have frequently said on this blog that guys should wear the “right boot for the right application.” For example, smooth leather-soled cowboy boots are not a good choice to wear when operating a motorcycle.

Muddy work boots don’t go well with a suit in church. Tall motorcycle patrol boots look best with breeches tucked into them. Lug-soled boots for motorcycling. Dressy cowboy boots with dress clothes in an office.

However, this blog post will discuss my feelings and observations about different styles of boots and features. I definitely have my own opinions. What are they?

First of all, I encourage men to wear boots every day, and never flip-flops. But other than that, I know that different men prefer different styles of footwear for different reasons.

For me, I prefer clean, shined, dressy cowboy boots to wear to work. I work in an office with other professionals. I usually wear a shirt & tie, and try often to shuck the tie.

Being a confirmed Bootman and known to wear boots every day, I will be adventuresome and wear bolder boots to the office. Brighter colors, intricate designs of inlays and stitching. But at the office, my pants are always over my boots. I may enjoy wearing boots, but I go along with the office norms.

There are some styles of dressy boots that I won’t wear — such as ankle boots once made popular by Florsheim. Similarly, I do not own and will not wear boots with Cuban heels. These types of ankle boots are not my preference. I don’t like how they look.

Does that mean that the boots are bad? No. It only means that I don’t like them. I know some guys who don’t like cowboy boots or don’t like motorcycle boots. I like both kinds of boots. Everyone is different.

I will not wear platform boots made popular in the disco era of the ’70s. Again, I don’t like them. I prefer styles that are more masculine and no way could I manage to wear heels that are 6-inches (15cm) high (or higher)!

And while I like cowboy boots, I generally avoid wearing cowboy boots with higher heels than a standard walking heel. Why? I am a klutz. I trip easily. But I also do not like how high heels feel on my feet. Again, it is just a personal preference.

I own and wear higher-heeled boots, such as my Legendary cowboy boots, custom Lucchese Classic pointed-toe high-heeled boots, or Olathe buckaroo boots. I do not wear these boots from my collection that often, though. I find that I prefer boots with lower heels that are easier for me to walk in.

For motorcycle boots — I have raved for years about Chippewa Firefighter Boots being about the most comfortable, durable, easy-to-maintain boot I have worn for motorcycling. I wear them frequently. But I also own and wear many other styles of motorcycle boots, including engineer boots, harness boots, motorcycle patrol, and tactical. I like them all and wear what fits my whim at the time I am preparing for a motorcycle ride.

However, I have preferences regarding motorcycle boots, too. For example, I own many pairs of Wesco boots, but because they are so heavy, I choose to wear them only when I will be riding more than standing or walking. Those boots definitely are not hiking boots.

Speaking of hikers, though, I own one pair of Chippewa hikers that I wear for long exercise walks that I take every weekend. (Unfortunately, I do not have time to go on a 1 to 2 hour walk during the week.)

An entire additional category of boots that I wear regularly are work boots which I wear to do physical work such as home repairs, remodeling, construction, or work around the house. I particularly am enjoying my Chippewa Arroyos biker/cowboy/work boots. These boots are rugged and have a great Vibram sole for motorcycling, yet have a cowboy boot design. They are heavier than the typical cowboy boots because they are built with thick leather and rugged construction of a work boot. I wear them often.

What boots do I not own or wear? Besides Cuban-heel ankle boots and platform boots, I do not own boots used for sports like skiing or polo. I don’t play any sport, particularly sports that involve snow or balls (or snowballs.)

Over time and with experience (both good and bad), I have developed my sense of personal preferences regarding boots. I like boots that look good with dress clothes that I wear to work in my office and feel comfortable all day; boots that do the job when I am doing repairs or work around the house; and boots that give me solid support and traction when I ride my Harley.

Life is short: wear boots, but know your preferences.