Take more chances with your look.

A true suburban 90s kid, the first piece of clothing I coveted was of course a pair of baggy Tommy Hilfiger carpenter jeans. You remember the ones, with embroidered logos on both the back tag and the carpenter loop. That was the fourth grade, when fashion was more about fitting in than standing out.

I wanted these SO BAD. My mom got me a pair and saved my 10-year old social life.

Like anyone, my look changed as I figured out the identity I wanted to project to the world. Preppy in college (Ralph Lauren and Vineyard Vines), upscale casual in my first job (Billy Reid), and, finally, full tech bro (Patagonia, Lululemon, and company swag).

Lately I’m feeling like I need a new look. It’s probably not a coincidence this is happening as my work identity is in flux. But also I think I’ve just been lazy in how I dress for the past few years. I used to care a lot about my wardrobe, but in the past few years I’ve cared a much less. Making more opinionated clothing choices gives you a “look.” And there are benefits to having a look:

  • You’re more memorable
  • Your personality is more salient, making interactions more successful
  • You can find more and more interesting margins to explore in your wardrobe; not just “I’d wear that” or “I wouldn’t” … new possibilities at or just beyond your comfort zone

I feel like I don’t have a look right now. Maybe soon I’ll find a fresh one. If you have suggestions, let me know! Everyone should have a look.

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