As you might imagine, we get a fair amount of middle-aged men that come into our store because their wives told them they need to buy some new clothes. About a third of the time, they’ve been told they need to get something better for work; and, two-thirds of the time, they’ve been told they need to buy some “cooler” clothes. A lot of guys struggle mightily with what to wear to the hip new restaurant in town. and in helping a receptive customer a couple weeks ago, he wanted to get some new shoes to go with his new jeans.

Amidst a number of shoes I like with jeans here, here, and here, he asked about the Spur -- a boot. I was surprised he considered a boot since I, rightly or wrongly, have grown to think that only card-carrying shoe queens like me really appreciate boots.

Since the customer was a trader, I tried to put my thoughts in a way he’d understand, which led me to say: "Boots are pure upside."

It didn’t translate at first, but then I explained: men’s dress boots are rare, I assume, because most men are told they need to own other shoes first: black dress shoes, brown dress shoes, cordovan, a chocolate suede if they know what’s good for them. So a guy has to feel like he owns all the basics before he would even consider a pair of boots. By the time he gets there, his black shoes have worn out and he buys a replacement pair of plain ol' black dress shoes. So if I see a guy in dress boots, I automatically assume he’s a man of means because he’d be crazy to have boots as his primary dress shoes.

So let's say you're walking down the street in those Michael Toschi Spur pictured above, other people are seeing your really nice shoes. Mission accomplished. But then, when you’re lounging in the bar area waiting for your table, legs crossed, your boots reveal their full glory. Again, sadly, most people won’t notice. Those that do, will immediately assume you are a man of style. Pure upside.

I recognize 99.9% of the male population has never put this much psychoanalysis behind a shoe style, but then again, that’s my point: when the one-tenth of one percent see your boots, you’re in the club. And if you’re in my club, the first drink is on me.

If you don't yet own a pair, shop all our boots here.