Tall Boots for Men

I am asked from time to time what manufacturers and styles of tall boots I like to wear, and do I enjoy wearing tall boots over my pants, jeans, or breeches. This post is about my preferences for tall men’s boots, especially nowadays where my lower legs have lost muscle tone with age.

There are four basic styles of tall boots designed for men. They are…

1. The Equestrian Riding Boot

Made popular hundred(s) of years ago, men wore tall boots when their primary means of transportation was a horse. These adapted Wellington boots became known generally as Equestrian Boots. These boots kept the mud and muck from soiling and damaging clothing (that was usually hand-made and not easily replaced.) It was very common that all adult men wore tall boots. (See this post for a history of how men wearing boots has changed over time.)

These days, men who ride horses for dressage, show jumping, equestrian competition, or for horse-driven sports such as Polo, wear modern-day equestrian boots. (Sometimes called “long boots” or “English riding boots.”) These boots come up to the knee and are sleek and conform to the rider’s legs (which are usually slender.) These kind of boots must be custom-made for older gents (like me) to accommodate a larger calf circumference.

The Dehner Boot Company began its business making equestrian boots of fine calf leathers, and they still make them today, though their boots are very pricey. Alternatives for those less inclined to pay over US$1,000 for a pair of boots are made by Ariat, Devon-Aire, and some other makers. Caveat emptor: if a pair of tall equestrian boots is priced less than $US200, be careful. Likely the boots are made in China or Pakistan of inferior products and with poor machine-made construction methods.

I personally do not own any equestrian boots and do not plan to get any. My only horse these days is made of 900 pounds of iron, steel, and chrome.

2. The Classic Tall Engineer Boot

Made popular when the railroads were being built and booming, engineer boots with the rounded steel toe and buckle across the instep were first worn as safety footwear for railroad engineers and operators. As motorcycles came onto the scene, men began wearing engineer boots for the same reasons that horse riders did — tall boots protected their clothing from dirt and damage, but also protected the rider’s legs from burns on hot exhaust pipes, and also during a fall or crash, of which there were many.

I own and regularly wear tall engineer boots. My favorite are those made by Chippewa. The Chippewa Hi-Shine (model 71418) boot looks great, is leather-lined, and is built very rugged and sturdy. Many motorcops wear them (as seen on my bike cop galleries). These boots are easy to maintain and last for years. A brilliant shine makes them stand out among the crowd.

I also equally prefer to wear oil-tanned Chippewa Engineers (model 27909). These classics never go out of style. A real “man’s boot” if there ever were one. Tough. Rugged. Solid. Looks especially good when well-worn, broken in, and covered with a golden patina of road muck. These boots are affordable, and can take a lot of rough wear. I choose these boots when I know that I may be riding to a location where there is a lot of dirt, such as to observe a road race, civil war re-enactment, or even visit a county fair.

I also own some other brands of tall engineer boots, but find myself coming back to Chippewa more often than choosing other brands, especially Wesco Boots. Man, I love how rugged and durable tall Wesco Boss (engineer) boots are, but I find their weight to be exhausting, especially if I wear them to walk around at a destination to which I have ridden my Harley.

3. Motorcycle Patrol Boots

Worn by motorcops, tall patrol boots are worn with motorcycle breeches. Their sleek design is very similar to tall equestrian boots (which is why some cops call them “horse boots”.) Tall, black, and shiny, these boots are attractive. That is among the reasons why so many people notice them, and the man wearing them. His boots represent a tough, masculine job that earns respect among the masses. (See what I mean among the >1,700 photos cop galleries.)

I have a large number of police patrol boots. While you see me wear Dehner boots often, my personal favorite are not made by Dehner, but are made by All American. I only have one pair of All American Boots (they’re darn hard to get), but they remain the most comfortable and best-looking patrol boots in my boot stable.

I have to say, though, over many years of some mild “boot lust” about patrol boots, there still is something about Dehners that turns my crank like no other patrol boot can do. I guess that’s where my gay genes are showing just a bit (giggle.)

4. Cowboy “Buckaroo” Boots

These boots are a western style of tall cowboy boot that men wear, especially when working while riding horses. Men who work on the horse ranch where I grew up wear them (but they also more frequently wear shorter cowboy-work boots, too.)

Buckaroo boots were made popular by Olathe (pronounced Oh-LAY-tha) and were once made in Olathe, Kansas, but are now made in Mercedes, Texas, when the company was bought in 1975 by Rios of Mercedes.

These boots have fancy designs on the shafts and the shafts are made of leather dyed with bright colors and contrasting stitching. These boots make a bold statement about the beauty of a tall cowboy boot. The boots come with a tall riding heel made with a spur ledge (onto which spurs are placed and used by some horsemen.)

I once owned two pairs of tall Olathe Buckaroo boots, but sold them to a friend since I was not wearing them. I just did not have the interest to do so — nothing wrong with the boots. They just did not suit my style any more. (Style preferences change with age, too.)


Generally, my preferences these days at my age and muscle-tone-loss calf circumference, I am finding that I am preferring to wear shorter boots. But I still choose to pull on tall boots some times, too. Mostly only now when I ride my Harley and on the few times when I am not choosing my favorite motorcycle riding boot, the Chippewa Firefighters.

And no — tall boots are not only worn by women. Secure, confident men can — and DO — wear them too. See this past post: Who Can Wear Tall Boots — Men or Women.

Life is short: wear (tall) boots!

3 thoughts on “Tall Boots for Men

  1. Note to your readers: Devon-aire boots can be very cheaply made, despite their price! I’d steer away from them if you are going to use them for serious horse-riding. For show or “play”, they would be fine.

  2. Dear BHD,

    Thanks to your blog I have gotten pretty confident wearing cowboy boots at work and around town.

    Just wondering, do you do ever pair boots with a large decorative/Western-style belt buckle? Or do you stick to plain belts?

    [I tried to post this comment on a 2012 post about matching belts to boots but the article did not allow commenting.]

    • Thanks for your message and comment. Glad to know that my blog has induced your confidence to wear boots at work and around town.

      I own only one “show buckle” that I won (as a young’un) in rodeo in Oklahoma, but it is more “normal size” (3″) than one of those large buckles you may have seen on display or worn by real rodeo stars. Anyway, these days, that show buckle is in an airtight frame so the silver won’t tarnish and is on the wall of my boot closet as a keepsake memory. I wear plain belts and buckles now.

      BTW, the capability to post comments this blog’s posts that are more than 30 days old is automatically turned off. I did that because my experience has been that comments on old posts are almost exclusively from spammers. I got tired of deleting all that junk so I just turned off the ability to comment on old posts.

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