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Step 1: Hair and Outfit
Try to wear something girly, but based on what type of Lolita you are-preppy chic, literally just pink and girly, or even punk rock. Hair is best curly or wavy (especially crimped) and possibly in fun colors, with hair chalk or wash-out dye. Wear pretty jewelry, like lace and bows. Good hairstyles are pigtails, braids and double buns.
Step 2: Makeup Prep
Apply concealers, bronzers, or foundations if you want. Also, put on some chapstick. I used:
-Shimmer Strips Vegas Strip/Light Custom Bronzer+Blush+Eye Shadow
Step 3: Eyes
You can make your eyebrows more comical if you want. Use sparkly shadow in a prominent color like pink, gold purple, blue, etc. and do the same with eyeliner. I am using my Urban Decay Vol 11 eyeshadow palette in Ecstasy, Sphynx, Half Baked, and Midnight Cowboy Rides Again. I am also using my Hello Kitty Charmmy Kohl Eyeliner Kit.
Step 4: Lips
Use a bright, possibly even neon, color like red, berry or pink. I am going over with teal eyeliner for a Lolita look.
Step 5: SFX
If you want, you can make a blush like kawaii lolitas have.