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I have white ones with pink polka dots. I figure they are goofy looking no matter what (but very practical) so i may as well have fun with them! I wear them when it's pouring rain and i have to go out in it, or if it's raining a fair amount and there are puddles and i don't want to soak my regular shoes. I don't worry too much about the outfit - i tuck pants into them to keep the pants dry, or wear them with a skirt if that's what i'm wearing, and i have a super cute rain coat that 'pulls the outfit together'...knowing though that ultimately the purpose of the rain gear is to keep dry.
i say ... just be shameless about it! stay dry, have fun, be bold with color and pattern, and wear them whenever there's enough rain to mess up your other shoes.
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- thanks