10 Fashionable Ways to Wear Loafers With Socks

My grandfather was very much into style. In fact, there are a few sartorial tips he ingrained in my brain long ago that I still think about today. One of which was to always remember the tailor (“Bobby, nobody likes saggy pants,” he’d say) and the other was to never forget about your sock choice because it does matter. And it’s true. While socks are often the afterthought to a look, the accessory is often quite noticeable when your pant leg lifts up, so it’s important to ensure that your sock game is on point.

On that note, one rule of thumb my grandfather also taught was to never wear white socks with black shoes. For many (Michael Jackson aside), this pairing was considered a “mistake” because black or multicolored socks were more appropriate. But as the fashion crowd continues to prove RN, it’s actually quite forward and cool to wear white socks with one of S/S 20’s most noteworthy shoe trend, loafers.

Slightly ironic in nature, this is one of those looks that feels “wrong” but is actually so right as an unexpected and simple way to bring a forward twist to any look. Some of the biggest designers have also been showcasing this styling trick in their recent collections. Chanel, for example, just sent a range of models down the runway for its S/S 20 couture show in black loafer-esque shoes with built-in white socks.

To dive into this trend a bit further, I’m highlighting some of my favorite street-style looks of the moment featuring white socks with black loafers. I also included a few runway shots below and shopped out stylish loafers (with socks to match) to perhaps inspire you to try this offbeat but cool look this season. I know I’m going to.