Q. I'm so glad your website turned up in my Google search! I took your advice (archive) over the weekend for Date #2 to a football game. Date #3 is dinner at my date's house. He is cooking and I'll be bringing the wine and myself. This is a great opportunity to see what he is like - his style, his apartment, etc. It's time for me to show him my casual, cute, funky side. What should I wear? I am 31 and I like to dress classically with something funky mixed in - like jewelry or fun shoes. I usually can pick out outfits but with this date, I am nervous and can't think straight!
A. Since it‘s about being cute and casual, go for items in your wardrobe that you can get comfortable in. For example, clothes that you can be cozy on the couch while you’re spending hours talking and enjoying wine. Wear dark jeans and a great camisole and wrap sweater or a great v-neck fitted cashmere sweater with velvet pants and ballet flats. Perhaps the flats are patent leather or animal print. And don’t wear too many layers since you don’t want to get overheated and give the wrong impression if you need to take something off. And since your signature seems to be the jewelry, wear one of your favorite necklaces or pair of earrings, but nothing too chunky or oversized. Keep your look pretty and feminine. And bring along a great bottle of wine and perhaps a mini pie or fresh baked cookies for dessert.