Here's my two cents on the subject...
Doesn't it depend on your intention and your circumstances to what age you decide to dress?
For instance not every crossdresser goes out in public. Although from this thread it looks as though the number of stay at home crossdressers is smaller than I thought!
Personally I would have a tough time "passing" going out in public. But posting photos is fine. Why? I'm six - four in bare feet, have a large Adam's apple, man face features and love wearing heels (size 14!). I'm slim so in photos it looks proportionate, so dressing in age appropriate clothing would not be helpful or allow me to "pass". I truly stand out in a crowd!
On the other hand if you love younger clothing and you feel comfortable going out like that. I say more power to you. Sure you'll get a lot of looks and people will judge. That's really the way of the world.
Personally I'm more uncomfortable with a MIAD out in public than an inappropriately dressed crossdresser. But hey, that's me!
