“Is something ever so wrong, it’s right? If there were ever a sartorial move that could evoke such an immediate, impassioned, and visceral response – the debate of socks with boat shoes might be at the top of the list.
There’s no gray area on the topic. You’re either in camp no sock or the presumably smaller camp pro sock. I’m not sure if it’s my natural contrarian ways or maybe just that I like to zig when everyone else zags, but the mere fact that the idea of socks with boat shoes is so controversial and off-putting to the majority of people makes me want to state an argument for it.
First things first – no “fun socks”. This is not a time for stripes, argyles, or novelties. Grab a crisp pair of white cotton socks and wear with your favorite chino shorts (cut above the knee!) and pair with a worn in polo, rumpled oxford cloth shirt, or breezy patch madras.
For a cooler day, substitute the shorts with a pair of chinos (not too slim, not too baggy) or a lighter wash denim like a broken in 501, and a vintage military shirt, cotton sweater, or chore coat.
At the end of the day, socks with boat shoes is a choice, not a necessity. Everyone knows boat shoes work well with no socks at all, but why not live on the edge, take a chance, and try something different – I’ll be right there with you.”
Brian Davis is the founder/owner of Wooden Sleepers, a New York based vintage American menswear brand, online store, and showroom.