College is actually a fantastic place to start wearing Lolita. If you have issues with your parents' approval of it, they're not giving you "the look" when you walk out the door for class. If your high school had a really strict dress code... well, I've seen people wear pajama pants, fox tails, and turkey hats to class. If you're incredibly self-conscious and/or shy, it's a little easier to keep in mind that a) there is a very small possibility that you will have class with any of the people you're surrounded by, and even if you do it's likely you'll never talk to them. Also, given the flow of students, with some leaving forever over the breaks and new people coming in... if you get your first coord over the break and you want to wear it: do it! Even on a small campus, there's not the "everyone knows everyone from the time they were five" mentality, or the problems that come with it, that's present in mandatory schooling.
I can see why some people might be worried if you go to school on a smaller campus where the professor knows you, you probably have him or her for at least two classes and it's been that way since you were a freshman (or, if you are a freshman, you're worried about it being that way) and the class sizes are closer to 35 than 500. There's a lot more individual interaction, and you generally start to sort of know everyone in your class. That's the kind of campus I'm on, and I've never had a single problem. I've been an admirer of Lolita since high school, but I started wearing it last year and I haven't had an issue. If my professors comment, they tell me I look very nice, or if a classmate comments, they tell me they like my shoes. The professors that I have for a million classes don't bat an eye anymore, and professors I've never had before might glance for half a second longer but make no comment.
For walking to class, my advice is to, if you're nervous, put headphones in, and just listen to music as you walk to class. If you need to, don't even look at people around you. But, after a while when your confidence is built up more, start looking at people's faces, if you don't usually listen to music on the way to class, take the headphones out and listen. Yes, I've had people give me the "what in the-" look as I walk by, but that's really about the most that happens. And there's plenty of good things that happen too: the lady at the cafeteria register absolutely adores my dresses, and she'll tell me I look like a little doll; people will tell me that I look so cute or "you look so nice, what's the occasion?" and when I tell them I just felt like it it's more along the lines of "that's awesome!" rather than any kind of negative reaction.
College is a really good, safe, place to wear Lolita. If you're just now starting to wear the fashion, or if you've been scared to wear it in high school but want to make it more of a daily thing, college campus' are a wonderful confidence boost.
Just for fun, here's a picture of the anime club booth at last year's "Organization's Night" (Club Rush)- as you can see... all types of people! (I'm in the middle!)
