In years of working with creative people, I've learned just how deceiving looks can be.
Pete's a good example. He really looked the part of a 1980s ad writer. Every day, a fresh blue button-down shirt, blue blazer with brass buttons, cordovan shoes polished a rich ox-blood, and a serious paperback under his arm. He talked the part, too. Go with him to a third-rate bar of his choosing, and he'd have critiqued every ad in The New Yorker by the time your prime-rib-au jus-on-a-French-roll arrived. He could also imitate talk-show hosts perfectly. If you missed Johnny Carson, he'd do the monologue for you.
Trouble was, Pete couldn't write. Every ad he wrote was as interesting as instructions for a washing machine. The language stilted, the plot hokey, the dialogue contrived.
Sharon was another example. She always came to the office dressed as if we called her in from gardening. She would've been great if we had an organic gluten-free account, but we didn't. The closest we could come up with was a whiskey account. She refused to go meetings, and was too shy to speak in meetings anyway. But, boy, could she write about the rolling fields of grain and the limestone water in whiskey. We told her she didn't have to go to meetings. Stay in your office and write. The guys from the distillery never knew their ads were written by Rebecca of Sunnybrook Farm.
The most complicated case, though, was Richard, because he was never the same two days in a row. One day he was as sharply dressed as a Men's Warehouse salesman, and the next day he showed up looking like a telephone lineman after a double shift. One day Mr. North Face, the next day Bowler of the Week. You never knew who you were talking to, and soon you were the one having an identity crisis. I tried to find the relationship between his productivity and his persona, but I couldn't. Clients loved Richard. He was Brooks Brothers at meetings. His writing was buttoned up, too.
I'm still looking for the connection between wardrobe and writing. I remember growing a full beard when I was secure in my job, but shaving it off when I was interviewing for a better one. When a writer wears a tie, he's probably covering something up.
When you're starting out, it's probably best to dress a little on the conservative side. Until both you and your boss agree you've got ability.