Q. I just bought a pair of brown topsiders, and I have no idea what to wear them with. I'm not actually particularly preppy, and I feel like a poser in a polo and khaki shorts... any outfit ideas I can incorporate these shoes into?
A. Boat shoes (or topsiders) are making a comeback this season, along with the ladylike loafer. Of course they look great with nautical-inspired clothing (see Blake Lively below), but the trick to wearing your new topsiders in a non-preppy way is to wear them with anything you might wear with a ballet flat: skinny or cropped pants, short skirts, and even summery dresses like the Karen Walker runway look below.
In addition to the traditional brown topsiders you bought, there are plenty of fun colors and even wedge styles available this season. Here are some of our favorite boat shoes worth trying: