Boots With Shorts?

I received an email the other day from someone who asked,

What’s your opinion on boots with leather shorts? I have really tall 18″ Chippewas and 18″ Wesco boots but I look like Sponge Bob Square Pants when I wear them with shorts. I have some 8″ Carolina boots I could wear. I am looking for a suggestion.

My response probably would not surprise you…

BHD: Hi, thanks for your question. Sorry, I am not the one to ask about wearing shorts with boots (or anything, for that matter.) I do not wear shorts myself. My body type is not suited to wearing shorts.

If you think you look like a cartoon character when wearing tall boots with shorts, you have answered your own question. Take a pass. Wear tall boots with jeans or leather. They look better that way (my opinion.)

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Continuing on with my commentary:

Some guys look really good wearing shorts — you know the type — fit, muscular, and usually young. (Or younger than me, anyway.)

Shorts worn with a polo shirt or t-shirt (and usually with sneakers), many men look hot. While that’s not “my look,” I realize I am the exception rather than the norm.

As men age, our legs look generally awful. Even if healthy, veins, ridges, and sagging muscles are obvious. (I speak for myself!)

One would think, then, that wearing tall boots might cover up the worst of the outward appearance of these features of older men. No, not really. While tall boots will cover the lower legs, the area of the legs between the bottom of shorts and top of footwear still… look… well, I’ll say it, ugly.

I also have a personal opinion that wearing boots with shorts just looks “off.” A very few really good-looking men can pull it off, sometimes quite well, but they’re the exception rather than the rule for us average Joes.

The few times I have been to Folsom or leather events in San Francisco (a long time ago), I always wore full leather and tall boots. I more-or-less enjoyed the “eye candy” of guys dressed in full leather and dressed like they were. Full leather was always comfortable to me, and to this day, I still enjoy it.

I was fortunate that when I was at Folsom, I was with the man I married. He was gorgeous in full leather, so I always enjoyed having him in my bed after the event (and always, since we had a closed relationship and didn’t fool around with other men.)

One may ask me, “Hey, I know you spend a lot of time on Puerto Rico and love the island’s beaches. You don’t wear shorts? Ever?”

Okay, you got me. I may wear something that looks like shorts (long leg bathing suit) and either “reef shoes” for when I go into the water and perhaps walk on shells so my feet need protection, OR short hikers to get from the car to the beach, then take them off and walk barefooted on the sand.

Inside my home-away-from-home in Puerto Rico, I may indeed wear shorts, but pad around in bare feet.

I *h*a*t*e* sandals and flip-flops and just can’t wear those things.

So there you have it. My opinion (only.) Wear boots with leather or long pants and drool over the few men you may have seen at Folsom who can pull off wearing leather shorts with boots. Not me.

Life is short: know what works for you and stick to it.

3 thoughts on “Boots With Shorts?

  1. I’m literally wearing shorts and boots right now, haha. I personally love the look, and I got several types of shorts to match with my many pairs of boots. I got this summer punk vibe going on and in most cases, really makes my boots stand out more!

    • Good for you! Enjoy! If you are happy with it (wearing boots with shorts), go for it! With my build and body, this look isn’t for me. Again, my
      personal opinions remain my own.

  2. Same opinion as mine. I prefer wearing tall boots with skinny pants, waist coat and a newsboy hat.

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