> Honestly, one of the things I absolutely love about tech/Silicon Valley is nobody cares at all how you dress.
Things aren't quite as loose as you seem to think. If you want to see where the boundaries are, start gradually dressing more and more informally, and note when you start drawing criticism from your manager and senior coworkers. I expect you'll get more attention than you want if you were to come to work shirtless, say.
I dress for myself. I dress well, casual and comfortable. I shall not wear a suit to suite others, nor will I dress like a bum. I have found a set of clothes I like, looks good and I feel comfortable I. And I buy five-to-ten of the outfits and I wear the same thing visually every day, though they are physically different garments.
Things aren't quite as loose as you seem to think. If you want to see where the boundaries are, start gradually dressing more and more informally, and note when you start drawing criticism from your manager and senior coworkers. I expect you'll get more attention than you want if you were to come to work shirtless, say.
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