I think I am one that dresses too old :P I am 22 but I can dress really conservatively and sometimes I feel like I dress much older than what I am. I used to look young for my age, always getting carded at bars, even refused lotto tickets once because the cashier said my id had to be a fake because I looked younger than my id :S
But now I never get carded! So for the new year I am trying to find that balance between dressing classy and dressing for my age. Sometimes it's hard to find things that I feel comfortable wearing, I find that skirts, and dresses are often too short.
Both of my aunts like to dress like teenagers. They're both attractive for their age and relatively fit, so it's not like they look gross or anything, but there's always something unsettling about seeing 40 year old women in Abercrombie t-shirts.
My mom dresses too much like an old lady. I'm trying to show her that she doesn't have to try and dress like her sisters but she shouldn't be dressing like my grandmother.