Sometimes it ain't hip to be a hipster. Your favorite bands do car commercials to make a quick buck, corporate shills infiltrate your quaint neighborhood for the cool factor and when the temperature dips the uniform of above-the-knee shorts and boat shoes gets shelved for more weather appropriate gear.

Wallowing in self pity can really mess up your socks if you're not rocking the correct footwear and fortunately there are options that will help you take your boat shoe style into the breezier days of Fall. Here are some boat shoe/chukka hybrids that let you keep up the preppy front while you keep your ankles protected from the winter winds.



3Sixteen x Quoddy Deck Peanut Grizzly Deck Chukka

Contemporary brand 3sixteen joins forces with age old boat shoe maker Quoddy to produce this marriage of old and new styles. The contrast white sole give the shoe some whip appeal while the body constructed of suede nap makes it look like you actually been putting in some work in these things.

$345 at 3sixteen.com



Yuketen Double Ring Boot

Double ring belts are usually hard to work but the cool closures on these Yuketen shoes seem worth the effort. The oiled leather upper combined with a Vibram sole guarantee that these shoes will last longer than a full screening of the Lord of the Rings Trilogy. "One ring to rule them all" and two rings to close them.

¥48,300 ($528 USD) at Museum Ark




Timberland x Stussy 7 Eye Boots

Double OG status. If you grew up anywhere close to the 90's you had a pair of fresh Timbs in your closet and if you've ever touched a board to surf or skate, you've probably done some shredding in Stussy. The two brands collaborate on two colorways of the Timberland 7 Eye which is basically a boat shoe with a growth spurt. Limited 80 pairs per colorway, trying to get your sea legs in these boots might leave you up the creek without a paddle.

Available at Stussy NYC




Band of Outsiders for Sperry Top-Sider

The general consensus is that when something is made of flannel it's more than likely warm and cozy -- like a bear hug. This aesthetic optical illusion is the thinking behind these Sperry Top-Siders designed by high fashion newbies Band of Outsiders. The high top boat chukka decked out in warm weather material bring your feet the look of a rugged outdoors man . . . or a butch lesbian.

$240 on sperrytopsider.com




Red Wing Wabasha Chukka 9149

Red Wing boots have gone from utilitarian workboot to the "cool guy" shoe of choice state side, but as usual the Japanese have been up on them since Jodeci was still together. With that in mind, Red Wing has been producing shoes strictly for the Japanese market to spite us for our lack of early adopters. These Wabasha Chukkas are a perfect example of Boat Shoe/Chukka and of why we need to learn Japanese Kanji

$300 available at Japanese Red Wing Retailers


Bonus:

Instead of listening to the sirens singing you to toward the jagged rocks, its better to listen to these guys singing about the reasons why we don our deck shoes in the first place. I can tell you one thing, it ain't for the seamen.