Ah yes, the rolled up double t-shirt. I remember those days. I also tight-rolled my jeans.
There was a period of about 9 months that I was on the prowl for a bomber jacket. I don't think I ever got one. Not while they were still in style, anyway.
Another trend that I went for which makes me absolutly shudder now was the colored bands on my braces. I had blue braces, red braces, purple braces and yes - even green ones. My orthodontist would even color coordinate for the holidays, alternating red and green for Christmas and pastels for Easter. Orange and black for Halloween. Well, you get the idea. The green bands sort of made me look moss-mouthed. Not attractive.
Now I realize why I never smiled in any pictures taken during middle and high school.