I believe that lolita fashion isn’t just about putting on a really cute dress– there’s an entire aesthetic that needs to be considered, and you can be wearing the rarest, cutest, most amazing Moitie-and-Angelic-Pretty-collaboration-radioactive-macarons-on-a-cross print ever, and you won’t look like a lolita if you don’t put effort into your all-around appearance.
In keeping with a theme I unintentionally developed of saying very non-PC things here in my blog, I’m going to say that, yes, I think all lolitas should do their hair and wear some kind of makeup, unless their hair and skin is naturally perfect (and even though I know a lot of beautiful people, I’ve yet to see anyone who fits that description). Yes, natural beauty is great. And yes, all people should feel proud to be who they are and to have their own unique personal attributes. However, I for one can’t see the point in going through all the effort of putting on really cute clothes if you’re not going to wash your hair.
I think a lot of lolitas, especially those just starting out, run into big problems when it comes to makeup. I think it’s important to consider that the makeup you wear in your everyday life might not be appropriate for the days when you dress like a cupcake (or, depending on your style, a vampire). Wearing extremely heavy makeup while wearing a bright, cute frock is going to make you look like Baby Jane, and you certainly don’t want that!
The kind of makeup you wear is largely dependent upon your personal style; that said, it is usually more appropriate to save your thick black eyeliner for your gothic looks and go for a more natural look with sweet and classic lolita. 
The age-old adage “What Would Mana Do” doesn’t really apply to things that Mana wouldn’t be caught dead in. And anyway, just imagine what all that eyeliner and mascara would look like on a girl in a frilly yellow dress! Ghastly!
I think Gothic Lolita in its true form is extremely striking; it’s also more mature than it’s sweeter counterparts. Makeup that is too neutral will make the wearer’s face seem incongruous with the overall look. However, white makeup is almost NEVER a good idea unless you’re going to be in some kind of play, or you happen to BE Mana. Your foundation should never been too different a shade from your natural skintone, if for no other reason than you will invariably end up exposing your natural skin color at some point and everyone will find out anyway.
That doesn’t mean it has to be boring, though. After all, sweet lolita is rather over-the-top to begin with so you might as well have some fun with your makeup. I think it’s especially fun to experiment with eyeshadows– colors are the way to go! Recently the trend I’ve seen on a lot of Japanese lolitas is to wear one shade of eyeshadow and a different color eyeliner and yet another hue of mascara. This gives the entire face a really playful, fairy-like look and adds to the fantasy of the outfit. Just make sure to not go overboard, and coordinate your makeup! I can’t tell you how many times I’ve met people who insist that they should wear blue eye shadow with every single outfit.
Also, experts will tell you that you should choose between a strong eye and a strong lip when doing your makeup. With gothic you might be able to get away with having dark lipstick and deep eye makeup, but with sweet I think it’s safer to stick with a colorful eye and a natural, if very shiny, lip.
As with any kind of fashion, what you’re really looking for is makeup that compliments your overall look. If the makeup is too flashy it will overpower the outfit; too plain and your beautiful face will take a backseat to the clothes you’re wearing.
I recommend carrying oil-reducing sheets with you. Flash cameras tend to bring out the worst in people’s faces, so a little dab before the flash goes off might save you the trouble of photoshopping later. This is especially useful for people who cannot wear foundation due to allergies.
If you do have various skin conditions that prevents you from wearing the usual layers of concealer, foundation, blush, etc, adding a touch of lipgloss and some mascara will give you a more finished look. You might be surprised at how far just a little bit goes.
Remember, when you’re wearing lolita, the dress shouldn’t be the only pretty thing! Your bound to feel a lot more confident, as well, if you have the whole package.
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