First Date Clothes for Dummies

Putting this look together will be a walk in the park—whether or not you’re going on one. Trying to win her that teddy bear at your local festival? Feeding the ducks at the zoo? (No really, you must really like this girl). Look good doing it.

Rugby Black and Blue Flannel Shirt ($79.50)
Meet your new favorite flannel: Rugby’s Black and Blue Flannel Shirt (available at Rugby.com). It’s warm and already has that perfectly worn-in feel.

Kenneth Cole Sagan Nylon Jacket in Black ($119)
Still too chilly? Add Kenneth Cole’s Sagan Nylon Jacket in Black as an extra layer of warmth. Offer it to her when she’s cold and she’ll be impressed by your chivalry—and your style (available at Kennethcole.com and most department stores).