Or be sneaky...
Tell her you were thinking of changing your image and you need her advice when you go shopping. If this works out try to go shopping late in the day and then ask her out for a drink to thank her for her help. You'll wearing the new clothes she picked out so she's gonna like how you look, now it is just up to your wit and charm. You'll be sitting on the porch in thirty years time with you grandkids reminiscing on just who was that masked poster.:-)
ttyl