I am blessed with a large family. I have many great nephews, one of whom will be starting high school on Monday. Like all kids his age, he insists that he is “his own man” but dresses like a clone. “Just the right” sneakers, jeans, and t-shirts.

He told his grandmother — my sister — the other day that he wanted a pair of boots to wear to school. “Uncle [BHD]’s boots are bad-ass!” (Direct quote). Both his grandma and mother referred him to me. What happened?

Well, at first, connecting with each other was challenging. My great nephew (GN) only communicates by texting, and I block texting on my cell phone. I have no use for it, and don’t want to pay for it.

I sent him an email, but did not get a reply. Finally, I called his home, spoke with his mother, and then got him on the phone.

“Hey, dude!” — our greeting to each other. “Did you get my email?” I asked. “No. Did you get my text?” he replied. “No.” Woops, the classic difference in our ages and styles of preferred communication were evident.

“I hear you want a pair of boots to wear to school. Would you like to go look at some boots?”

GN said, “sure”. The next evening, I rode to his home on my Harley and picked him up. I wasn’t all too happy that he was wearing sneakers, but at least he was wearing long pants. I handed him a helmet, went over the safety precautions, and we mounted up. I was going to remedy that “unbooted” situation!

There is only one boot store in the area of my home state near where my GN lives, which leaves little choice. I was not, however, going to ride all the way over to Virginia where there is a better selection. Not at rush-hour on a weeknight! Traffic on the interstates is awful, and not worth the aggravation and danger on a motorcycle riding two-up in a sea of law-breakers who text and yap on hand-held mobile devices behind the wheel.

When we arrived at the boot store, we were greeted by a friendly guy dressed as a cowboy — you know the type: slim Wranglers, boots, cowboy shirt and the requisite Stetson. “Howdy” he said with a broad smile. “How can I help you today?” Then he did a double-take. He looked at me again and said, “are you that guy with that website about boots?” Oh darn, “outted” again (giggle.)

I said, “yep, that’s me. So if you’ll give us some time alone to look over your boots, we would appreciate it.” I really don’t like salespeople who hover next to you when you’re browsing at a store. I know they want to be helpful as well as guide you to making a selection that not only fits your needs but also provides them a better commission. He took the hint, and said that he would be available when we had any questions.

My GN was impressed with the selection. My thoughts? “Meh, I’ve seen much better.” But for GN’s first visit to a boot store, seeing 30 pairs of boots on display, with some others stacked on boxes in various places, was impressive.

First decision: “what do you mean by ‘bad-ass’ boots?” Cowboy boots, motorcycle boots, or a hybrid? GN said that he wanted a pair of motorcycle boots, and that he didn’t want to look like “that cowboy” — pointing to the salesman. (Knowing smile… don’t overdo the cowboy look. It doesn’t really work in Maryland.)

That narrowed down the selection quite a bit. We were left with five pairs of boots to look at.

I began with instructions to read the label inside the boot shaft before doing anything else. “Where are the boots made, and who is the maker?” We found rather quickly that three of the five pairs of motorcycle boots on display were made in China. Two pairs of Harley-Davidson branded boots and another pair from some company I’d never heard of. These three pairs of boots were instantly ruled out. No cheaply-made but overpriced boots from China!

That left two: one pair of harness boots and another pair of engineer boots — both by Chippewa, made in the USA. I described each style of boot to my nephew, and reviewed the construction, soles, and quality. The cowboy salesguy was impressed. I heard him say to a colleague, “that guy really knows his boots!”

I asked the salesguy to measure my GN’s foot using the store’s Brannock Device (that’s the name of the metal thing that you stand on to measure foot length and width, so you know if you’re a 9C or a 12EE in U.S. measurements.) The salesguy did that correctly. My GN was a 9D. I asked the salesguy to bring out both styles of boots in a 9D.

He went into the back room and returned with one box of boots. He said that only the harness boots were in stock in size 9D, but the engineer boots were not. He had them in either an 8D or a 9-1/2D. I know that Chippewa engineer boots run a little large, but thought that since my GN is still growing, it may be okay to get a larger size and grow into them, so I asked the salesguy to bring out the 9-1/2D engineer boots.

My GN tried on both pairs of boots. He thought the engineer boots were more “bad-ass” than the harness boots, but he didn’t like the fit. “My feet are really sliding around.” I thought that might be the case.

What made the selection for my nephew was what the store had in stock in his size.

I thought that was “it” when my GN noticed another guy his age with his father looking over cowboy boots. The other guy pulled on a pair of plain distressed brown Justin boots and walked in them. You could hear the heels of his boots making that distinctive “clunk” on the wood floors in the store. I could tell that my GN was keenly interested.

I turned to the sales guy and asked, “can you make a deal, such as buy one pair, and get another half-off?” The salesguy spoke with his manager, and offered a compromise — buy one pair full price and get another pair of equal or lesser value for 70%. Okay, we can live with that. (You know, it never hurts to ask for a deal. The worst they can say is “no” — but you don’t “get” unless you ask!)

So I asked my GN if he were interested in a pair of boots like that other guy was wearing. I could tell — I know “the look” — that he was. I asked the salesguy if he had a pair of those Justins in my GN’s size. He did.

GN tried on those Justins, and I could tell that he really liked them. Darn comfortable boots, and not overdramatic. Just plain old comfy boots to wear to school with jeans. So I bought the boots for GN as a gift. “My treat, from your Great Uncle Bootman.” We both laughed.

My GN was happy with his purchase of Chippewa harness boots and his gift of Justin cowboy boots. We put his Justins in my Harley’s TourPak as well as his sneakers, and he put on his Chippewa harness boots, donned the helmet, and mounted my Harley confidently (while that other kid his age and his father were watching in the parking lot). He looked cool and was happy to be seen “booted” on the back of my Harley as we passed some of his friends on our ride home.

I look forward to hearing about his first days in school next week, wearing those “bad-ass” boots!

Life is short: ditch the sneakers — wear boots to school!