I was at an event recently, a surprise 40th birthday party for a good friend that I used to work with. I got to hang out with a ton of people from my previous employer (huge health insurance company - rhymes with "you floss, you yield"). Anyway, as I caught up with people and wandered around the party nearly everyone commented on my wardrobe. I was wearing nice new blue jeans, leather soled loafers and a collared blue dress shirt. Which is actually pretty dressed up for me these days. But people couldn't get over the jeans. I confessed that I frequently wore gym shoes to work, at this point they said that I was just bragging...
I'm not comfortable all the time. I have frequent client meetings, and I suit up according to their dress code, but the rest of the time I dress for comfort.
How much is being comfortable worth to you? Would you accept a lower salary if you knew that you could dress in comfortable clothes every day? Or going the other direction, if you dress for comfort today, how much more would they have to pay you to get you to put on a tie every day, or wear wing-tip shoes?
Is one of the defining characteristics of the truly successful that they get to decide how they will dress all the time?