If you have to ask, you aren't cool enough to pull it off
Dressing for an occasion and one rule of cool
Hello friends! The weekend is nearly upon us. Before today’s entry in This Is The Way, I have two housekeeping items for your awareness.
1) Tomorrow is our First Friday e-lunch for members of This Is The Way. We hang out for an hour, get acquainted, talk about weighty issues, and generally just foster relationship with one another. If you’re a reader, there are more folks out there like yourself who love pop culture and self-improvement who you can meet in our little community. Upgrade to Paid today and join us!
2) Two months ago I opened an e-store called Living Star Wars. Without much expertise in merchandise or selling, this was a little too heavy a lift for me. But my friends at No System stepped in and we’ve begun a merch partnership for This Is The Way. No System is an apparel hub for free thinkers and genuine rebels, and they have a section carved out just for you. The first piece of apparel is inspired by Qui-Gon Jinn of Star Wars: The Phantom Menace, and his words “Your focus determines your reality.” That is a foundational idea behind this newsletter. The notion that self-control, moderation, temperance, these things are not for prudes…they are for people who want to have a say in how they experience the world. We’re not powerless. Our choices, the things we focus on, those things become our world. Hop on over to No System and check out “Focus Determines Your Reality” using promo code THEWAY2022 to get a sweet discount.
Who are the coolest characters you know of?
I’ll start: Indiana Jones, Tyler Durden, Star Lord, Qui-Gon Jinn, James Bond, Ellen Ripley, The Dude, Han Solo and this one guy on cable news named Jimmy Failla.
You know “cool” when you see it. These characters know who they are. They either know exactly what they believe about the world or are far too flexible to be pinned down by idea, sacred cow or dogma. You can’t quantify or qualify “cool”, cause as soon as you have a working definition that is what opens the door to it being subverted. And it will be subverted.
During the inaugural First Fridays lunch for This Is The Way supporters, we had a group of readers/thinkers/fellow travelers discussing a wide range of subjects including the midterm elections, parenting, self-confidence, and ego. Big thank you to everyone who showed up last month to get acquainted.
If you have to ask
One part of our discussion focused on dressing for work events (such as conferences, interviews, or galas). I wanted to share one of the takeaways from that discussion — a little lesson I picked up from a visit to Fox News in New York City many years back.
It was 2019, and I was in NYC to do Fox Business’ Kennedy in the evening. Kennedy is a fun show. They intentionally mix political talk with humor and even some games over the course of the hour-long show. The lead writer of the show is Jimmy Failla. This guy is more New York than pizza rat, and he’s also incredibly (if not unreasonably) kind. Failla splits his time on air sporting window pane suits, gunslinger button-downs, and leopard skin blazers. Failla does his thing whether its morning, noon or night on Fox News and without much consideration for who he’ll be sitting with at the table.
Because he knows he belongs there.
I was in the “green room” getting ready for the show. Reading the show topics and hurriedly skimming news articles so I’d be prepared for the lively panel discussions on Kennedy. They can be very lively. For a guest on this show, over-prepare and under-prepare at your own risk.
I’d brought my denim jacket up to NYC with me. It’s cool. A nice sharp blue and covered in patches of all my favorite things: Star Wars, Ryan Adams, America! What else could one need?
And here begins the tortuous moment where we stand before our wardrobes or mirror and fret endlessly about what we’re going to wear, and what that choice says about us to the all-important public.
I was there on business, so I’d also brought a more formal blazer with me. I didn’t know which to wear. I’d brought the denim jacket because I was toying with the idea of going casual and just “being myself” rather than my work-self who suits up and tries very hard to sit up straight and say clever things.
Jimmy was in the room saying hello to all the guests, being his usual swell self and warm host. I put on my denim jacket, walked over to Failla, and asked him if I could wear it for the show (instead of the usual suit).
Jimmy grinned, “Kent, if you have to ask you are not cool enough to pull it off!”
Damnit. Jimmy was right. And in the end, I didn’t wear it. I walked out in my work costume and did my thing. It went great, by the way. Because to be clear, I feel more comfortable suiting up than dressing down. When I’m in that mode, being that person, I feel like I belong in settings like this. You ever felt like that at a dinner or conference? Dressing a bit more like me, the me that my family and friends experience, I don’t feel like that person belongs in NYC on anyone’s TV.
If you have to ask, you aren't cool enough to pull it off
It took me another few at-bat's on Fox to even reconsider what Jimmy had said to me that night in Midtown. Eventually, I did dress the way I wanted. A button-down, a nice tie, and a denim jacket. To me — that is perfection.
And I didn’t ask. Han Solo would never. You shouldn’t either.
This is the way.
Don’t forget to grab the FIRST of several to come This Is The Way t-shirts and streetwear. Use that code THEWAY2022 for a discount! Pick up Your Focus Determines Your Reality here.
I am thinking of switching to cloak, like a Franciscan monk. But I live in Houston. Maybe they make a light, cotton version.