“As the co-founder of a sock company (shout out @bombas), you would think my answer to whether to wear socks with Sperrys would be a reflexive “yes”. That I would be an easy plant on the wrong side of a lopsided debate. But my stance on socklessness is more nuanced than that.
I believe that because I started a sock company, I have earned the right through years of sock scholarship and dedication to go sockless whenever I please. And I please often.
That being said, I happen to have an inside track on all the reasons why many of you would want to wear socks every day, for every occasion, and I am here today to stand up for my #alwayssocks army.
When I think of Sperry, I think of Paul Sperry’s classic boat shoe and the original CVO sneaker (potentially even more of a classic than the boat shoe, but we can address that debate another time). For the CVO, a classic Bombas calf sock or a sly cushioned no show sock is entirely appropriate. For the boat shoe, we’re in trickier territory. But that is where the low-cut no show comes in to play.
If you must wear socks, and I know some of you out there must, this sock was invented for the sole purpose of yielding the floor to the boat shoe, the ballet flat, and other low vamp staples.
Note that it does not look good on its own, but once it’s inside your Sperrys, it will disappear completely, giving you the advantage of stealth comfort. Sockless looks, sock feels. Best of both worlds. ”
Randy Goldberg is men’s style leader and the Co-Founder and Chief Brand Officer of Bombas.