Lolita is Victorian and Rococo inspired fashion. The style was born in Japan somewhere in the 1970's. It is unsure exactly how and when Lolita came to be. The fashion is focused on appearing "beautiful," "cute," and "sweet," rather then "hot" or "sexy."
There are "rules" and guidelines that are too be fallowed to qualify an outfit as Lolita. Rules such as a bell shaped skirt, a pair of knee high socks, headwear, etc... To learn more about the anatomy of a Lolita outfit you can visit this link
There are many different styles and sub-styles of Lolita. Some of the most popular of the styles are Classical, Goth, and Sweet.

The Word "Lolita"
If you go to Google now a day and look up the word "lolita" you're bound to find two things...
1) "Lolita" a novel written by Vladimir Nabokov published in 1955. The story is famous for it's controversial subject: A middle-aged Humbery, who becomes obsessed and sexually involved with a 12-year-old girl named Dolores Haze (also known as Dolly, Lolita, Lola, Lo and L).
2) Or Lolita the fashion. "In Lolita fashion, it is generally accepted that "Lolita" does not refer to Vladimir Nabokov's famous novel. In the context of fashion, the term 'Lolita' does not relate to sex. The usage of the word may also be considered wasei-eigo..." stated in Wikipedia.
Classical Lolita

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Classical is probably the tamest and most Victoriana inspired of the styles. Unlike Sweet Lolita which mostly focuses on looking cute and child like, Classical Lolita tends to focus more on being classy and beautiful.
The majority of Classical skirts are A-line rather than bell shape.
Rarely are bold colors worn in this style outside of royal blue and red. As the colors tend to be more soft, make-up is also suggested to be the same.

Gothic Lolita
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This style is primarily influenced by Victorian inspired goth styles and not cyber goth or industrial styles.

The attire of a gothic lolita looks much like Victorian morning clothing with it's dark colors, puff sleeves and bell shaped skirt.

Make-up for this style can be anywhere from neutral to as heavy as smocky eye shadow.

Sweet Lolita

(I do not claim any rights to these photos)
Sweet Lolita is the most childlike and over-the-top of the styles. It's inspiration is still drawn from Victorian clothing, but not as much as the Classic style.

This style tends to use many bows,  ruffles, pints(animals, candy, flowers), and accessories. The colors of this style are mostly on the pastel side.

Neutral make-up looks best with this style. Cute bouncy curls or pompom pigtails are commonly worn.
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