I think that my preference for the practical (that is, comfortable) has skewed my perceptions a bit. Not just because my situation as a poor graduate student meant that I spent most of my time holed up in the house working at the computer in my pajamas and never having a need for nicer clothes, but also because as a fat and relatively tall person so many things just look awful on me no matter how cute they might be on the hanger. So I have little tolerance for things that are not comfortable, and a very small range of options for things that even fit properly in the first place.

As a result, 90% of the styles that have been "in" for the past 10 years or so just don't appeal to me at all. I either know that they will look terrible on me, even if I like them, or I can't find them in my size, so I just give up on the look. It's hard to pick apart how much of this is a sort of defense mechanism and how much is genuine preferences.