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Time Will Tell

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Time Will Tell

Steve Jobs may have reinvented the black turtleneck at one point, but most tech guys aren’t known for their sense of style. More likely, they’re known for a complete and utter lack of it. Hoodies. T-shirts. You know the outfit.

I was a tech guy for a long time. You get the picture.

Even my friendship with Angel, or involvement behind the scenes at A|B, didn’t change the way I dressed. I thought suits were suits. Ties were dumb. And since I have an iPhone, I thought watches were a waste of time.

But a few years before I sold my company, things started to change. I had a lot of big meetings. I met a lot of investors. The more I found myself in rooms with really well dressed people, the more I started seeing the difference a nice suit made. It wasn’t just appearance, it was presence. Not that I was showing up in a hoodie, black socks and Vans, but I wasn’t dressed like them.

I also started noticing little details. Pocket squares. Ties. How they pulled an outfit together. There was also some practicality to both, and deep down, I’m a pretty practical person. I could wipe my brow with a pocket square and look good doing it. A tie could hide the fact my tailored, slim-fit shirt was ballooning out between buttons when I sat down, revealing my bellybutton. The better I dressed, the more confident I felt. To put it simply, it was weird. But very cool.

Still, the practical side of me from Indiana Amish country still made it hard to rationalize the cost of some of these items. Especially shoes. Every bone in my body said spending $1,600 on a pair of custom shoes was crazy and they couldn’t possibly be worth it. But shoes were really what wound up pushing me over the edge. And Angel was the one who pushed me into the shoes that took everything to another level.

Now I own 4 pairs of custom shoes. The difference I feel in walking, I can’t put a price on it. I have had chronic back issues for years, but it feels great after a day of walking in handcrafted shoes. They change my day. My mood. My energy level. Above all that, they look amazing. The stitching, firmness, material, craftsmanship of something like a pair of St. Crispins is amazing. I quickly realized, if the shoes were worth it, maybe everything else was too.

That’s really how I started appreciating custom clothing. Being Angel’s friend didn’t hurt, but again, I’d been Angel’s friend a long time and really didn’t get it, or even try. But that was then. I’m still not necessarily sold on watches yet, but our recent trip to the Brietling headquarters and a weekend with George Kern and his wife may change that.

Only time will tell.