24, server What are you wearing? A top and skirt from Buffalo Exchange, a necklace from the Guthrie Theater gift shop and Triple Five Soul booties from shoes.com.

What's your favorite item of clothing? Ever? No clue.

What's the best way to strike up a conversation with a cute stranger? Smile, be yourself. But I've got a man.

What's your strategy for outfit coordination? My outfit tonight is built around the skirt.

30, science teacher What are you wearing? Pants from Express, boots from Everyday People and a cameo necklace from my Great Aunt Delores.

What's your favorite item of clothing? This shirt. A student of mine designed it when I was teaching in Bangkok.

What's the best way to strike up a conversation with a cute stranger? Ask them what their biggest fear is.

55, experience designer What are you wearing? Zipper coat and raw silk scarf designed by Kara Tharaldson and me.

What's your favorite item of clothing? A "spotted beaver" suit adorned with oyster and crimson silk flowers.

What's the best way to strike up a conversation with a cute stranger? Don't use your voice. Use your body. If you see a great dancer, join her.

Strategy for outfit coordination: I like to coordinate adventure and romance.

23, production assistant What are you wearing? A vintage shirt, an Urban Outfitters dress and vintage accessories.

What's the best way to strike up a conversation with a cute stranger? Easy for me -- I usually say "Hi, I think you're cute."