This conversation is interesting to me, as a 47yo artist and DJ who feels a lot younger and lives a casual, fairly non-conventional lifestyle. Granted, I'm on the other coast, where style is definitely more buttoned-up, but someone in my lifestyle could wear cutoffs and tees almost every day and no one would bat an eye. I have friends of all ages who rock those boho 70s styles, so I don't think it's age-restrictive.
Elle, you look great, but I understand why you're asking the questions you are. The further into my 40s I've gotten, the more I've questioned whether certain looks are right for me, but the words "age-appropriate" don't enter my mind as much as "sophisticated" does. I just got rid of the last of my items with short puffed sleeves -- I have hit a point where they look dated and unsophisticated to my eye and *for my style.* Somehow things that didn't seem too girly last summer seem all wrong now.
Bottom line to me is, wear what you enjoy. If you feel fab in something and it's not getting in the way of personal or professional goals, then go for it. I wear shorts (although not short), bikinis, and sleeveless tops, even though I have cellulite (and I'm not overweight). I'll be damned if I'm going to cover my arms through a 95 degree, 80% humidity Baltimore summer for fear of offending someone's eyes with my dimpled flesh. The day will probably come soon enough that I feel the need to cover more up, so for now, I just relax and enjoy some freedom.
All the same, I am always looking at my wardrobe with a critical eye these days to assess whether something is a style I'm aspiring to or simply settling for.