Middle School and High School
Provided you don't go to a school with a very strict dress code or a uniform policy, it is possible to wear Lolita to school. I know quite a few people that wear their frills to school all the time. There are a few things to think about though before you decide on your outfit. First and most important, will I be breaking any school rules by wearing this? Many dress codes have a policy on what you can and cannot wear. Consult your school handbook to check those rules. It shouldn't be a problem if your school has a fairly lax dress code, but double check to make sure. Second, do you have any sort of art class that could be messy and leave stains or gym classes that would either require you to change? It's best to avoid wearing lolita on those days. You do not want to be stuffing expensive and delicate dresses into gym lockers or risk staining them with paints or chemicals. Make sure your schedule will allow you to wear lolita without risking your clothes. Finally, do you mind getting rude comments, stares, questions, etc? Kids can be really mean to each other, especially if you look different from everyone else. Prepare yourself for all sorts of comments, questions, and all those nasty looks.
College is so so much easier to wear Lolita at. Very few colleges and universities have uniforms or even dress codes. Unless your school is extremely small, people really won't bother you, make comments, etc. You'll still get the occasional question, comment, and plenty of stares, but overall it's not nearly as bad as High School or Middle. Again, you want to avoid wearing lolita on days where you might have messy activities (Chemistry, other science labs, art, etc.). Take into account if you use public transportation that it may be crowded at peak hours. Other than that, I can't think of anything to really watch out for.
Think about what you'll be asked to do at work. If you work with food, machinery, or pretty much anything that could spill or leak, don't do it! Use common sense! Many work places if not all have dress codes or uniforms, so make sure your boss is okay with it. If they are, then that's great! Watch your skirts, they can easily knock over displays or get caught. Most everything from above also applies to work. You also might want to leave your wigs and OTT makeup off for the day, as customers and co-workers can be put off by these things especially.
As for styles, I think pretty much anything can work as long as it's not too over the top. Classic is a lot more "normal" for people that don't know anything about the fashion as it passes for vintage style. Casual probably would work best as well as it would be more comfortable. The most important thing is to be comfortable and your outfit be functional. Have fun and don't be afraid to try wearing Lolita to school/work sometime!