Whatever you do, take care of your … socks?!
“I say, beware of all enterprises that require new clothes, and not rather a new wearer of clothes. . . If you have any enterprise before you, try it in your own clothes.”
– Henry David Thoreau in Walden
Thoreau: the OG Authentic
Have you ever come across a quote so perfectly you that you feel you should have written it, if only you’d been wittier, pithier, or perhaps born 150 years earlier? You know the type of line that would look great tattooed on your arm or something? That is how I feel about that Thoreau quote, but rather than permanently etching it into my body, I stuck them up on the wall above my computer I can glance at it from time to time. If you’ve worked with me since launching 27 South, you likely know why. These days, I take these words pretty literally—but that wasn’t always the case.
Several years ago, I got a talking-to from a boss about my choice of clothing for a meeting. Not just any meeting: a Zoom, at 8 p.m., in the thick of the pandemic. I was home with two young kids, exhausted, and grateful that I’d made it through bedtime with only minor casualties. The last thing on my mind was whether the two inches of visible sweater in my little Zoom box would offend anyone. I loved that sweater. I thought I actually looked nice!
But that moment stuck with me. I quietly promised myself that if I ever created my own professional space, I’d always prioritize the wearer over the clothing.
Headshot Outtake
So when I launched 27 South, I leaned into the garment that, frankly, brings me joy: hoodies. One of the perks of running your own shop is making swag, so I made hoodies with my logo in multiple colors. Maybe you noted my new headshot on this website and on LinkedIn (thank you Emerson College headshot booth!). My clients can attest, I wear one almost every day. Sometimes I rep my firm, other times a client (maybe yours next?!), the Antelope Running Club, Camp Avoda or whatever else feels right that day.
Now, to be clear: I know when to ditch the hoodie. Earlier this summer, I ran into a client at a conference who had only ever seen me on Zoom. When she saw me in a suit, the first thing she said was, “I didn’t know you owned anything other than a sweatshirt.” I do own suits and I’ll wear them when good judgment suggests it. But even then, I sneak in a bit of personality.
It started with Jerry Garcia ties back when I worked at the State House. These days, I refuse to wear ties at all (why is a knot around the neck “professional”?). Instead, I’ve moved the personality down to the socks. Phish socks, to be precise. Maybe I took their advice that “whatever you do, take care of your shoes” a little too literally, but I’m good with that.
The world famous Trey socks.
There’s a method to this madness. Most people never notice my socks, but if you know, you know. A few weeks ago, I attended a summit with business leaders, government officials, and academics. Backstage, the CEO of a tech company spotted my socks immediately. He got it. We spent 30 minutes geeking out about Phish and then set up a follow-up meeting to talk business.
That’s the point. In my business, and likely in yours, few things matter more than authenticity. When a client signs with 27 South Strategies, they’re not just getting top-tier strategy, representation, and insight. They’re getting me, the real me. In a world of carefully curated images and augmented realities, I show up as myself.
Maybe Phish isn’t your jam. That’s okay. But I do hope you have YOUR Phish and wear it, literally. You never know who will be tuned in to what you are laying down.
