While the boat shoe demonstrated breakout appeal from yacht clubs to city streets and college campuses, the shoe looks best when paired with summery outfits and bare legs. You can transition the boat shoe to spring and fall wear, but finding the right pair of socks is difficult. Your best bet to avoid a fashion fail: Downplaying socks or ditching them outright.
No socks with boat shoes is the most frequent and safest choice. While not the best option year-round, you can wear these shoes with bare feet from spring to fall, if the weather's right. As a cold-weather alternative, try nude stockings, which give warmth without a telltale sock line.
Stockings and tights help you pair boat shoes with skirts and dresses in a natural way. You can opt for nude if you want no color, or match the tights to the color of the dress or the shoe itself. If you're rocking high-heeled or wedge style boat shoes, stockings help keep the look classy. To make a style statement, try a bold color; to blend in for a sophisticated look, try black.
Loafer socks go super low, so you can wear any sock you've got on hand and no one needs to see it. You get the warmth you want in a sock, while keeping the casual look of the boat shoe intact. Sometimes you can have it all.
Boat shoes with visible socks are generally best left for men who want a self-conscious preppy style or aren't paying attention. If you want to copy this masculine prep look with boyfriend jeans, put on tall argyle socks and boat shoes. Otherwise, you really don't want to see socks with boat shoes.