I Was Told Not to Make This Shoe "Mistake," But Now It's All I Want to Do

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, 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.

The pop of white with the socks brings additional contrast to this all-black look featuring the cream maxi coat.

Heeled loafers and white socks are particularly cool with cropped straight-leg jeans. 

Remember that tip above with the jeans? Well, it applies to this look as well. This fit could easily become your new go-to elevated casual ensemble.

Dress up the white-socks–and-loafers vibe with a pretty statement dress.

Keep it casual yet sophisticated with your loafers, socks, jeans, and a white T-shirt.

Go retro with a pair of cropped flares to show off the socks and loafers.

The white socks here punch up the all-black fit even more.

And now for a little runway inspiration. Gigi Hadid wore white tights with ankle socks and loafers in the Chanel S/S 20 couture show. 

And here’s Kaia Gerber in the white-socks–and-loafer look in the same Chanel show.

Next, check out the best top-rated boots to buy now.