I dunno about that dress looking grandmotherly... because every old woman I know of where's some kind of slacks and ked shoes.
As for the initial questions on the topic...
What kind of makeup do you prefer?
I don't wear any makeup. I've tried. Every time I try to put anything on, I look like a little girl that got into mommy's makeup. My face is way too childish for it. ^.^
How do you typically dress?
In highschool I had a big gothic phase and wore a lot of black fishnet things as well as those bulky bracelets and belts. I even had a purple gothic schoolgirl skirt with a bunch of belts and chains. It was cool at the time. ^^ Now I just wear a lot of jeans and shirts. The shirts usually have some over the top cute drawing and saying on them.
Where do you getcher clothes?
Hottopic (yeah I don't care!) or
Loyal Army. Though now that I live in Germany I have yet to go shopping for very many clothes...so I don't have a place yet, but there was one store that had adorable bunnies with nerd glasses on the front that I got...
What's your skin/hair routine?
I straighten it. It's naturally curly and icky but some people say they like it. It's alright that way but I do the whole blow-dry then straighten most of the time. If I'm feeling lazy I leave it curly...but it makes me feel like Shirley Temple :<