Comfy or stylish all the time because I basically wear leggings ans a big sweater or t shirt out with my hair up I only dress up when we're doing something nice like eating out or for work I wear stuff like this link
It depends on the girl, but I love it when a girl has her own style and takes the time to show it rather than throw something on that's just comfortable. I can't stand girls that don't care for their appearance like wearing stuff like basketball shorts.
As with candy, the contents are more important than the wrapping. Although, I do like girls who have a relaxed/casual look while still maintaining some sophistication/classiness. Basically if you don't dress like you are planning on walking the streets that night, you're okay in my book.
I don't care what a girl wears to feel comfortable, but she's gotta be able to dress up for the occasion. That's cool you have a style and know what you're into, but if you brought that for a day at the beach I'd think you were stupid.