On my way to an online meeting this morning, my wife stopped me. She seemed downright concerned and asked, “You’re not really going to wear that cat t-shirt on video, are you?”
I definitely, 100%, was going to wear it, I assured her. “I mean, it’s an internet job, isn’t it? What kind of internet guy would I represent myself as if I didn’t wear a cat t-shirt? That’s the real question.”

She rolled her eyes and made some remark like “it’s your funeral.”
Truth be told, I don’t always wear cat t-shirts to video- or in-person interviews. Most of the time, it’s rock & roll t-shirts, as I’ve made a dedicated effort to amass quite a collection over the past half-dozen years. Though, for meetings, I try to at least wear my newer ones.
That’s kind of where I’m at style-wise these days: The more important the meeting, the newer the t-shirt I’ll wear. And this cat t-shirt was brand-spanking new. (See pic!)
I admit this sounds a little crazy, and even counter-intuitive, but ever since I founded Array Web Development in late 2010 / early 2011, I decided that the superficiality that I always ascribed to business suits had to go. I never felt comfortable suits and/or ties, to be honest — not at Prentice Hall, not at Deloitte, not in any of the management roles I’ve held. For better or worse, I’m just not a suit guy.
So, when I struck out on my own in 2010, I tossed 100% of my suits and ties. My own mother died later that year, and I had to borrow a suit for her funeral. (And, even there, I kind of didn’t like the fact that I was wearing one.) I swore, after that, that I’d just never wear one. And by now, I think most people know me well enough to not invite me to places where I’d need one.
Anyway, when my first big meetings came up in Portland, I felt downright hesitant about my ultra-casual dress (basically a t-shirt and a hoodie), but was resolved to dress on my own terms (“comfort first”) from then on out.
But guess what? The clients I met either (1) didn’t care, and/or (2) were just as often dressed more informally than I was. And I landed the work dressed like that, time and time again. And not insignificant gigs, either. I’ve walked out of board rooms having inked $40k deals wearing Beatles t-shirts!
To me, this verified what I’ve long believed — that substance matters more than style. At least insofar as web design, web development, SEO, and digital marketing were concerned. Your mileage may vary!
And sure, why not? After all, I may never have been a particular fan of Steve Jobs or Mark Zuckerberg, but they got away with the same thing — Jobs (formerly) with his signature black shirt and jeans, Zuckerberg with his painfully plain gray shirt and jeans. Of course, no one knows who the hell I am, but why not “Jim and his t-shirts”?
I didn’t get the gig today, though.
Maybe it was the cat; maybe not. That’s the thing with informal dress. When you win the work, you can say with confidence that the cat shirt didn’t matter. When you lose, you have to accept that you’ll just never know.
If I’m being honest, I probably just flubbed something else (stumbled over my words or something). But if it was the cat t-shirt, would I have really been happy doing that work? I think not.

✍🏻 Jim Dee maintains three blogs — Hawthorne Crow, Web Designer | Web Developer Magazine, and Wonderful Words, Defined — and contributes to various Medium pubs. Connect at JPDbooks.com, Amazon, FB, Twitter, Instagram, LinkedIn, Medium, or Jim [at] ArrayWebDevelopment.com. His latest screwball literary novel, CHROO, is a guaranteed good time.







