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What To Wear On A First Date If You're Not 20 Anymore

5. Wear Chic Dresses With Comfy Shoes
If you don't love heels you don't have to suffer for fashion in order to look stylish on a first date. You can most definitely wear comfy shoes and still look fashion forward. The trick is just choosing shoes that match your frock - play around with your options until you find ones that go with your outfit.