(SOURCE: Dolce & Gabbana)
The best way (personally speaking) for someone that is interested in getting into lolita fashion is to first learn about the distinctive "anatomy." After all, it is what got them interested enough to learn more about this one-of-a-kind Japanese street fashion.
The standard lolita outfit consists of (a) headbow, (b) blouse, (c) jumperskirt, (d) over-the-knee socks, (e) mary jane shoes and (f) bag. See figure 1.1.
Figure 1.1
Note the hair is natural and neatly styled, the makeup minimal, giving it a simplistic look.
However, the ideal lolita outfit is more detail oriented, commonly; (a) wig, (b) fake eyelashes, (c) circle lenses and (d) fake nails. See figure 1.2.
Figure 1.2
This look is "dressing up to the nines." The makeup is heavy, the wig is voluminous, there is much detail to the outfit. You could say its less casual.
Now onto the undergarment layers which are super important. It is basically half the look, literally!
The undergarments are typically (a) bloomers, (b) petticoat and (c) camisole. See figure 1.1.
I would advise any beginner to start out with the standard, along with a petticoat. The camisole and bloomer undergarments are optional. Well, kinda. The camisole acts as a barrier between you and the dress, keeping the dress a little more clean. You could also use sleeveless, v-neck tops which maximizes the efficiency. As for the bloomers, they're designed to prevent any embarrassing Marilyn Monroe moments, but shorts would work, too. Petticoats are the only undergarment that is absolutely not optional! Petticoats are the magic behind the super fluffy lolita dresses! Otherwise, you get a sad looking dress, much like a deflated balloon! It is, like I said before, half the look! So please invest in a petticoat before anything else!
Which petticoat? Where to buy?
Stay tuned for Lolita Style Lessons: Chapt 2 - Petticoats!