Maybe it’s all the boating/pirate stories in the news lately: The nautical shoe is officially back and hugely popular, even outside the boat yard. I love how it offers a fresh alternative to sneakers and loafers. And the newest versions manage to be timeless and hip. Check it out: Sebago just debuted an amazing new line of streamlined deck shoes (look at that patent leather model!) designed with the trendy street-wear collective, VANE New York. Meanwhile, J. Crew has teamed up with Sperry to create its own perfectly broken-in, chambray-lined series of dock shoes. Even Colette, the cult Parisian fashion boutique devoted to all things cutting-edge, introduced a small, exclusive line deck shoes by La MJC this spring.

Special bonus: The more you break in nautical shoes, the cooler they look.

Tips: Don’t wear boat shoes…

• with socks
• in winter, unless you live in a hot, tropical climate
• with pleated khaki shorts or baggy polos and t-shirts.

Boat shoes can be inherently Caddyshack or Kennebunkport-esque, so your goal is to urbanize them a bit.

Tips: Do wear boat shoes…

• with slim, clean-lined jeans, trousers or shorts. Dark or white denim (rolled up or not) works especially well.
• If you’re female — with a pretty tee or fitted top (to keep things girly) and a short trench coat. Or, if you’re a guy, a good t-shirt, laid-back camp shirt, or button-down and blazer are all great options.
• In neutral colors — unless you’re a true style adventurer with the confidence to pull off red or kelly green footwear.

As Donna Karan points out in the March issue of GQ, ”There are quirky men who can carry off quirk, but most men can’t.”

Here, some of my favorites:

Spinnaker/VANE, $110 at sebago.com

Docksides/VANE, $110 at sebago.com

Original nubuck chukka Sperry Top-Siders, $125 at jcrew.com

Sebago Dockside shoe for women — limited edition model via La MJC: $176.54 (VAT excl. at Colette.fr

Much love,
Loren