Guess what! I'm having a date tonight!
Yes, a date and like every other woman in the world I have a closet full of nothing. I have no idea what I should wear tonight. As a Lolita it's even harder to find an outfit for your first date because you want to show your date your individual style but at the same time you don't want to overwhelm him with your ruffles. (On a side note, if the guy says something like "Lolita is ugly, I don't want to be seen with you in Lolita", he probably isn't worth your time :/ but that is for you to decide!)
You may not want to wear a full OTT Lolita outfit with circle lenses, wig and fake lashes, since it is about you and not about how perfect your outfit looks. Most of the guys don't like it if you look like you painted your face with several different colours :D But I have a post about "first date make-up" in my make-up blog, so check it out if you want to know what I would wear for such an occasion.
Even though I like sweet Lolita, i won't be wearing it tonight, only because I don't like to wear pastels only in my everyday life. But that's just me and my personal preferences. If you want to wear pastels on your first date, go ahead and do so but keep in mind that you want to keep it simple.
This is the only "simple" pink dress I own, I would wear this dress with a cutsew and without a petticoat. The cutsew keeps it casual and, to be honest, this dress looks better without a petticoat. You can combine it with a blouse and wear it with a petticoat if you like. As long as you feel comfortable, it's fine.
A very classy combination would be a simple JSK with a blouse or cutsew. I love this dresses cut. I wear it as a "normal" dress as often as I do in a Lolita combination. But I wouldn't wear it today without blouse and socks because we'll stay at his place to watch TV and I will have to take my shoes of. It is possible that he is totally grossed out be naked feet, so I don't want to risk anything ^^ (I'm totally grossed out by naked feet, that's why I thought about this :D)
If you have big boobies, like a C-cup or bigger, you want to avoid under-bust cuts. It will make your boobies look HUMONGOUS! You don't want your outfit to scream "Hello! I have HUGE breasts! Stare at them!" at the first date :D
Also, dresses with a babydoll cut aren't the most faltering. Sometimes they make you look "rounder" than you are and if that makes you uncomfortable, you date will feel uncomfortable too.
You don't like dresses? No Problem! Put on a skirt and pair it with a cutsew or blouse. A cutsew, once again, would be the more casual version. I choose this skirt because it's not too fancy and I know my date digs suspenders.
In the end it's up to you. Wear what ever you are comfortable in. If you want to wear a light blue ruffle monster, do it! If the guy likes you, he doesn't care what you wear!