Rolex Submariner w/ NATO Strap

Mille Miglia Jackets by C.P. Company

Watchviewer Mille Miglia Jacket ($620 at Identity Menswear)

These distinctive jackets, designed by Italian label C.P. Company, debuted in 1988 for use in the Mille Miglia, a thousand mile rally race through Italy. They feature a detachable hood with integrated goggles and some have a clear window on the wrist to allow you to check your timepiece under the sleeve.

High Performance Cotton Mille Miglia Jacket (via Found NYC)

Hood and Goggle Detail

3 Pocket Mille Miglia Field Jacket ($433 at Casual Clothing)

Vintage Diving Watches

Nothing says classic cool like an vintage diving watch. Built to stand up to the rigors of undersea exploration, these functional timepieces are highly sought after and dope as fuck.

Military Issue Rolex Submariner

Korbold SEAL

Omega Seamaster ProPlof

Via ScubaWatch.org

Arrow Moccasins

Canoe Moccasin (99-130$ depending on type of sole)

For 45+ years, this Massachusetts company has been handcrafting a wide variety of moccasins, which are relatively cheap compared to other premium moccasins. Available in single leather sole, double leather sole and crepe sole, Arrow even offers custom made moccasins if you send them an outline of your foot traced onto a piece of paper.

Lace Boot (110-129$ depending on type of sole)

Via Arrow Moccasin Company

Napapijri Skidoo Jacket

Never heard of Napapijri? Neither had I before I stumbled across one of their jackets on an online skiing store. Although most of their jackets have Norwegian flags on them, Napapijri is actually a high end Itallian outfitter of arctic geographic expeditions. Their pullover Skidoo Jacket (450$) is especially dope and features a raccoon fur-lined snorkel hood and kangaroo pocket.

Via The Startingate and Purple Oval

Sperryations: Sebago

In this day and age, it seems as though every shoe company has put out a boat shoe to compete with Sperry Topsider, who created the original boat shoe in 1935. Sperryations (Sperry+variations) is an attempt to chronicle these impostors.

For our first installment, Sebago Docksides.

Sebago Dockside (90$)

Out of all the Sperryations out there, this one is most like the Sperry Authentic Original. First appearing in 1946 (11 years after Sperry), Sebago Docksides come in a variety of colors including black, which is one of the gripes I have about Topsiders. Sebago also offers an array of tri-colored boat shoes as well, which in my opinion look the freshest.

Sebago Spinnaker (90$)

Via Sebago