Mo, these days I try very hard not to do this, but I have certainly been guilty of it in the past. I've had more than one forehead-smacking moment of realizing that I no longer want to wear a prior "absolute favourite", even though I've only worn it a handful of times. Because I was "saving" it for an occasion. No more!
I don't worry too much about upsetting environmental norms. I often dress a little different, a little more arty, I guess, especially now that I live in the suburbs, but unlike others, I have never had a snide comment. People must be nicer in Vancouver, ha. Although we have a reputation for being an unfriendly city...maybe it's just that we have better manners? No, I'm joking of course. But really, it makes me sad to think that women would subtly put down other women because of how they dress, or that people might dress differently than they'd like out of a concern that their sartorial choices might invite comments. I honestly don't think I've ever, ever had a snide comment. People sometimes say very sweet things, actually, especially about my shoes or coats, or sometimes hat. (Hats definitely invite comments). My kids' teachers and principal often comment that I look "put together" or "stylish" or something along those lines, but it feels like a compliment, not a jealous snark.