So it's getting warmer, you're a dude, and you have no idea what sort of footwear to wear with your T-shirts and shorts. You're not really into the flip-flops (for fear of looking like a Phi Beta Whatever) or the leather Jesus sandals (that I personally find quite lovely actually, but a close not-so-hetero friend of mine says they're reserved for grandpas and gays—go fig), and the Chucks-with-no-socks look has been wayoverdone.
Growing up in Southern California, I've noticed that docksiders seem to have been overlooked by the young-male and under-35 crowd—let alone the non-arrogant-USC-undergraduate-Tommy-Hilfiger-wearing-chino-pant-loving-J. Crew-worshiping crowd. In fact, I haven't seen them get much play this side of Hyannis Port at all, actually.
I'd forgotten about the way-too-comfortable topsider boating shoes until recently, when I spotted some modernized and modified Sebagos at a Pasadena shoe store. Suddenly, memories of my father sporting his burnt sienna-tan-and-black pair with solid Ralph Lauren tops and Dockers with his musky Polo cologne on the weekends came rushing back. And then I cocked my head and squinted: They actually look kinda cool now? (And of course I had to buy the women's pair in white—at a mere $68 a pop. Now I wear 'em with shorts and breezy tunics and blouses.)
A month later, I started spotting docksiders on everyone from hipsters in skinny jeans to band dudes in, uh, skinny jeans to dads in sensible shorts and khakis.
Sure, topsiders are preppy as hell, but as long as you avoid wearing them with Abercrombie button-ups, Polo Ts and khaki anythings, you'll be fine. Better than fine. Stylish,even. Contrasting the docksiders with "cooler," more contemporary items such as tailored, narrowed jeans or, again, your favorite worn-out T and cardigan would probably be the most fashionable way to do it.
The boat shoe is obviously of nautical origin (and we all know how in-style that look is nowadays) and is easily identifiable by its quasi-thick rubber sole, easy slip-on style and leather laces that run throughout the back of the shoe. Brands like Sebago or Sperry Top-Sider (available at Nordstrom) have been at it for years, with Sperry Top-Sider first showing up sometime in 1935, after avid sailor Paul Sperry observed his cocker spaniel Prince running across the snow-covered, icy ground and maintaining remarkable stability.
Yeah, nice story, guys.
But anyway, while the boat shoe is really meant for those who "can't live without the water" (sperrytopsider.com sure is informative!), that doesn't mean they can't look fantastic with the rest of your normal wardrobe—just don't throw that cable-knit sweater around your shoulders.