I think I speak for both Ryan and myself when I say that neither of us really have too much of a clue about what it means to be stylish, or really even why anyone would bother. In some ways, it can seem that those obsessed with fashion are, in the worst of cases, vanity-driven trend-jumpers without real substance, always looking for the next trendy high-dollar status piece.
I can only speak for myself when I say that I was one of those people who only noticed the ugliest, most noise-generating members of the personal style and fashion tribe, and often wrote off anyone who looked like they “invested too much time” into their style. Even still, when observing a person on the street who had a look that was well put-together without being deliberately ostentatious, I couldn’t help but feel undeniable respect. I kinda love having my ego jostled like that…
That’s why I was excited about this episode.
I had personally met Tommy a few times previously, so I knew going into it that he was a super-sweet, deep guy. He’s also one of these guys with a style that’s potent, confident, and not at all attention-grabby for no reason, which, to me, is undeniably worthy of respect. In my case, probably as much jealousy as respect. Ha.
Our conversation with Tommy was super eye-opening, and our longest to date. Of course, we dug into his creative process, fawned over his artfully-curated shop (where we recorded this one!), talked about the importance of story in business and its prevalence in high-end menswear, and even squeezed a few much-needed fashion tips out of ol’ Tommy. We covered some good territory, but barely got past the crust of this topic, as I continuously thought of so much more I wanted to ask for a few days after we recorded.
With a little luck, we’ll get a second shot at sitting down to record with Tommy, as he’ll no-doubt find continued success with his shockingly-nimble and COVID-appropriate business model. For that reason, I won’t get into all the unasked questions that came to me in the days following recording, but I will share a huge takeaway that slapped me in the face almost immediately after, and will keep me from ever judging another human for having a desire to be fashionable or look nice, and that’s this:
While high-fashion clothing design is inarguably an art form, one of the most basic and foundational forms of self-expression is in your look. Even without knowing, your look is showing a good bit about who you are, and what you’re trying to share of yourself with the world. A person’s “look” is no less artistically valid than their efforts to paint, sculpt, write, or whatever. And if you’re judging a person for their look, you’re probably as big a douche as me.
