When I was in fifth grade, I went to a private school that required students to wear uniforms: the boys wore slacks and collared shirts, and the girls wore little belted pale-blue jumpers. The popular girls wore the jumpers beltless, layering them over white or navy turtlenecks that were bunched at the neck (never rolled). I went for button-down blouses with enormous, frilly collars and tied that belt on exactly where it was supposed to go.
I was not cool.
I took a strange sort of pride in my non-coolness, actually. I remember at one point all the girls deciding to wear their scrunchies around their ankles, and making a conscious decision to keep my scrunchie in my hair where it belonged (despite my best friend's urgings) because it seemed pointless and weird to stick the thing on my foot. My choice to buck that particular trend made me feel pretty good, actually...in a small way it felt like a sign that I was doing my own thing, and that "my own thing" might be a kind of awesome thing to do.
And then, in the spring of that year, everyone (by which I mean Sarah and Nell and Katie and the other girls I wanted very badly to be just like) started wearing saddle shoes. I loved them. I wanted a pair of my own. But I felt silly about the fact that I wanted them; it seemed embarrassing to even desire the pair of shoes that was so clearly what the cool kids were into. I worried that it would seem like I was wearing them just to fit in, or that "fitting in" was actually what I did want.