You already got the basics down for how to dress Lolita, and you've RSVP'ed for an upcoming meetup. So the big question now is: what are you going to wear?
While New York City is the fashion capital of the world that doesn’t mean New Yorkers and tourists alike wholly accept Lolita as a fashion. They'll probably look at you and then walk away, whisper, or worse, follow you onto the train for further harassment. Now does this mean you should never wear Lolita outside and in public? Of course not. If you want to enjoy the company of your frilly friends without the incessant worry of being followed by leary eyes here are some things to consider:
Comfort is Key. Are you spending most of your times outdoors or indoors? Are you normally cold all the time? Wear a lot of layers you can take off if you get too warm. It's great to bundle up and preventing future colds, having sweat spots is neither ladylike or ideal conditions for hugging friend you haven't seen in long time. More than likely you'll be walking around a lot so opt for comfort than cute. Wear low heels (less than 2") or flats -- the lower heel creates less of an impact while walking so you're feet won't hurt as much since you're putting your weight on your whole foot instead of just your heel. I also highly recommend rocking horse shoes for those casual outings as well -- the foam platform soles make a nice cushion for your feet.
Be Prepared. You never know if there’s going to be a freak snowstorm or high chance of rain (it's always raining in New York City). I always keep a small folding umbrella in my bag because there have been times where it rains as I go home when there wasn’t a cloud in the sky. So check the weather report the night before or that morning of that scheduled meetup. I would also recommend you check mta.info before you head out the door. There’s a chance that the subway trains are running on time and then there are times where that train you need to transfer onto is not stopping at the station you need. Or map the place you need to meet on your iPhone/iPod or print out a copy of the meetup post - especially when you've never been to the area you're all going to meet up. Give yourself at least an hour before you leave your house/apartment–this way if you run into train delays you’ll be five minutes late/early as opposed to arriving three hours after everyone has left for somewhere else.
Keep it Simple. No matter where you are in New York City you will be walking to and from someplace. Try not to bring too much baggage. Unless it’s a bag full of gifts or you are returning borrowed items don’t expect someone to carry your second bag for you. You’ll probably carrying that bag all day, and it will get heavier by the end of the day after all that walking. So consolidate as much as you can, and think twice before you bring your DS (Are you really going to use it for the 20 minutes you're riding on the train?) or that latest Gothic Lolita Bible.
Be Confident If you are wearing Lolita, by definition, you’ve chosen to have the guts to look like you walked out of Candyland. Or Japan. Whether you are just wearing Lolita indoors to bake cookies or going out to see your friends you should have the confidence to wear something you like. Don’t make the clothes wear you. I strongly believe in wearing Lolita as a fashion and not a costume. Especially when people are more than likely to stare when they're not suppose to. If you wear Lolita like a fashion, people will disregard you less if you think you are wearing a costume. Show others you are wearing something that makes you happy. They'll see that and leave you alone, or give you compliments. Even better, they may follow in your footsteps.
Of course these are things to take to heart wherever you live. Is there anything that's a must-have advice for you that Lolitas should know about when hanging out in the city?