Too young:
- hoodies, if you're over 35, on either gender. Women are quicker to swear these off, but a lot of middle-aged guys in tech hang onto them for too long.
- Skirts more than a couple of inches above the knee, though there's some fudge factor if you wear leggings under them. And some people might say that if you've got great legs, you can still pull them off when you're older -- but to me, it fairly shouts, LOOK, LOOK, I'VE STILL GOT IT, and trying too hard is aging, IMO.
- A bright pink lip.
Too old (a lot of this is specific to my area):
- What I call Berkeley Schlumpwear: lots and lots of drapey layers in natural fabrics, to the point where the wearer's figure is completely obscured, usually worn with aggressively sensible shoes. I think the intent is an artsy, IDGAF look, but it takes exceptional confidence and a very strong personality to pull off, and a lot of women seem to go for this look to hide, not stand out.
- On both men and women: long hair that isn't regularly trimmed or conditioned. Ponytails with balding or thinning hair.
- Heavy eyeliner, powder or blush.
A lot of this comes down to looks worn with confidence and self-knowledge, I think. To me it's about looking like you're still engaged in the world around you, while at the same time having enough confidence to not try to compete with the kids, and dressing the body and face you have right now in a flattering way.
