A good friend up in NYC connected me with the reporter who wrote this article. She seemed amazed that I wear flip flops to the office once in a while. My response was basically summarized in that final quote below.

Cale Smith realized he had to change his style four years ago when he moved from Washington to the Florida Keys. The self-described “yuppie workaholic” brought along his wardrobe of dress pants and button-down shirts and immediately felt out of place.

“People gave me odd looks and thought I was a salesman,” said Mr. Smith, who is the managing partner of Islamorada Investment Management, where he manages two portfolios totaling $7 million in assets.

To fit in with his clientele, Mr. Smith changed his wardrobe to the more casual Keys style and sometimes even wears blue jeans and flip-flops to the office.

“If someone can show me the correlation between wearing a suit every day and portfolio returns, I’d be happy to wear a suit — despite the odd looks I’d get around town,” he said. “Around here, everyone is focused on performance, and that is all that matters.”

Wearing flip flops to the office is not always a conscious choice. I work a lot. I wear flip flops a lot. The two are not mutually exclusive. Plus, you just can’t buy socks anywhere in Islamorada. Seriously. Nobody sells them.

I think baseball legend Ted Williams summed up my position on this issue the best:

“I’ve found that you don’t need to wear a necktie if you can hit.”