Q. I’m going on a first date to a restaurant that describes its attire requirement as dressy-casual. I understand that means no jeans, but what are other ideas of what I should wear. Since it is a first date, I don’t want to overdo it and I want to be comfortable, but appropriate. Also, I’m in the Midwest, so it’s cold here.
-First Date Stumped
A. While I understand you don’t want to overdo it, there’s no reason you can’t still dress up a bit. I believe part of the fun of dating is dressing up and having fun with your wardrobe—it’s not your work clothes and it’s not the clothes you wear with your girlfriends. I’m a big fan of wearing a dress on the first date. A simple jersey dress with a wrap sweater or trim fitting cardigan sweater, tights and knee-high boots. It keeps you warm, it’s not overly dressy and you still show you put effort into your attire. If not a dress, then wear a skirt, tights, knee high boots and a pretty top. Skip the pants on the first date, you can always wear dark jeans and a cute nubby sweater on a date to a movie.
left to right: Ya-Ya Swan Sweater, $345 at shopbop.com; Rebecca Taylor Jeweled Cardigan, $284 + pencil skirt, $190 at shopbop.com; Diane von Furstenberg Besos Cardigan, $172 (sale) at shopbop.com; James Perse V-Neck Long Tunic and Stretch Turtleneck, $79.99 (sale) at bloomingdales.com