Millennials and Boots

There is some controversy about what defines generations, including those generally lumped into the class of “millennials” who were born roughly between the years of 1981 to 1997, more-or-less. I generally disavow lumping anyone into any category because I myself don’t fit stereotypical lumps. But that’s another story.

Anyway, I had an interesting conversation with three guys in their late 20s at a professional association social networking and mentoring gathering, and I thought I would convey the boot-related parts of our conversation. (I participated as an old-fart sage/mentor in my role as an officer of the association.)

The boot-related conversation began by one of the young men noticing cowboy boots on my feet, and saying…

“…cool boots. Different for a social event, eh?”

I responded that I wear boots like these all the time, not just for social events.

His reply was expected, “you what? Boots at an office? You mean like at a desk and in meetings? — not out on a field site, but actually with a suit in an office?”

His incredulity was palpable. His other two buddies about the same age were closely attentive. They also were a bit more than wondering about this “boots-in-a-professional-office” thing that I had going on.

One of the other young men said, “I’ve been taught to ‘dress like the person whose job you want’, not just what I want to wear. Hell, if I could do that, I’d be wearing my sneakers and jeans every day.”

But then the conversation changed a bit. First young man said, “Well, if I wore boots, I wouldn’t wear pointed-toe cowboy boots. That isn’t my style anyway.”

Okay, I can understand that. Not everyone likes cowboy boots. So I asked him, “if you did choose to wear boots, what kind of boots would you wear?”

Guy #3 said, “look at these!” and pointed to his own feet. He had on a nice pair of short dress boots. He went on further to say, “these are good looking, comfortable, dressy boots that I like a lot.”

The other guys looked at his boots and asked him more about them. “They’re ‘Thursday Boots.’ I saw them on Facebook and liked how they looked. The company that makes them was founded by guys my age. I like their style. They also were much less expensive than dress shoes. With my student loan payments, I can’t afford high-end shoes. So these work.”

Guys #1 and #2 both seemed to be impressed. Guy #1 said, “well, I’d wear boots like that. Not like those…” (pointing to my Lucchese Caimans.) Guy #2 said, “me, too. I saw those and some others like that, but haven’t gotten any.” Then he pulled out his smartphone and found the Thursday Boots website and actually made a purchase there on the spot. He remarked, “nothing like the present.”

Okay… I guess those wallet-sucking sillyphones have a purpose. I mean, if it gets a guy to buy boots, even short dress boots, I’m all for it!

So a brief moral to this story — yes, young men who are trying to “dress to impress” for promotion potential, who live on the U.S. East Coast, and work in a professional office can wear boots with dress clothes. Perhaps they are not ready for or not interested in traditional cowboy boots, but as far as I am concerned, any kind of boot is far better than a dorky dress shoe!

Life is short: wear boots!

5 thoughts on “Millennials and Boots

  1. Hey there! First of all, I gotta say I love your blog! I think I keep re-finding it every now and then but for sure I’m setting up an RSS to keep subscribed from now on!
    Second, as a 22-year old “millennial” with a very eclectic boot collection (44 pairs as of right now) I have to say that it’s true that not many peeps of my age appreciate boots in the same way I’ve seen older gentlemen do. I have managed to convince some of my peers and friends to wear boots in some way (heck, I’ve even lent them pairs of mine as a sort of “demo”) and most of them see the appear, but either consider them to be costly or simply too much of a burden to wear. The trends in boots that are of the taste of the “young’uns” I’ve met is usually around tactical boots, combat boots or regular work boots. Heck, I think the most popular type down here in Mexico are the tried-and-true ol’ cowboy boots. So yeah, I would say the boot spirit is not quite dead, and I’m trying my best to keep the flame alive around my social circles!

    • Rick, thanks for your reply. I’m very happy to receive it.

      I appreciate your interest and ongoing support of younger men wearing boots. The resistance, curiosity, and sometimes fear expressed by younger men toward wearing boots has been puzzling to me, so hearing from someone of the millennial generation gives me hope.

      Keep on keepin’ on the boots. Best wishes, BHD

  2. I’d like to add a bit to the discussion about quality. I’ve found it’s not so much the boots versus dress shoes viewpoint, rather how much you invest in quality footwear. Cowboy boots made with high quality leather gives a much different perception than those made from synthetic leather. I’ve been noticing boots made by Allen Edmonds and the thing that strikes me most about them is quality. They use the same quality and standards in the production of their dress shoes when producing their boots. Strict dress codes aside, it really boils down to personal style choice within parameters. Go for quality in whatever you choose to wear and you’ll be well-ahead of the game.

    • I agree. Quality outlasts, outperforms, and is a much better value for the long-term. I have several pairs of Allen Edmonds boots, and like them… though I am still struggling personally with their dorky-dress-shoe appearance.

      • It’s the wingtips that give me pause. Unless they’re two-toned, they just don’t suggest to me a sense of style, other than what might appeal to a middle-aged lawyer.

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