Several of you commented, and I had an email exchange with Ashley, about not thinking about what you put on in the morning. All hail, the people who dress on auto-pilot! You are in very good company. For example … Michael Kors. I remember hearing him answer a viewer question about this on one of those Project Runway season wrap-up shows. The viewer was suggesting that it was ridiculous that a fashion designer would wear the very same thing all the time. Presumably, wearing a plain black sportcoat and tee with jeans every day didn’t strike this viewer as a good marketing statement for buying designer clothing.
Kors’ response was that, as a young man, he wore all sorts of crazy things. But at some point, he found it easier to be creative in his designing when he wasn’t expending so much energy on his own wardrobe. So he figured out what looked good on him* and what was comfortable, wore that and stopped thinking about it.
I’ve got respect for that sartorial philosophy, especially the part about figuring out what’s flattering on you. I’ve tried to do this of late. For example, I have concluded that the crewneck looks awful on me. I am never happy with a crewneck.
But his response also makes another point: you have to choose your creative outlets. And that outlet ought to be something that is important to you, that you enjoy, and that inspires you. If getting dressed isn’t it, then, by all means, don those jeans and tees with pride. But wear handknit socks.
* Just an aside: I am a big fan of the sportcoat/t-shirt/jeans combo on men. Big fan.