first: red lipstick. it has that old hollywood glamour, femme fatale come-hither appeal that looks phenomenal when done right. it makes even the sloppiest of outfits and the messiest of hair look sophisticated, like you meant to be a mess because obviously you have red lipstick on. sadly, my skin tone has made it tricky for me to obtain this.
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second: glasses. i've yet to find the perfect pair to achieve that geek-chic look. i think girls look adorable in square glasses, preferably black plastic ones, but i also like tortoise shell.
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