Grab This: Sperry 75th Anniversary Canvas Sneaker

Update: Results

Sperry gives a heartfelt thanks to all who participated. They were especially excited and pleased about this giveaway, and would like to bestow a new pair of CVOs to the following contestants:

1) “I’d take my grandfather to the coasts of Normandy, a place he has not been since June 6th, 1941, but one that he yearns to see again.” — David

2) “Wherever my love wanted. Many men say they’d go to the ends of the Earth for a good woman. Too few actually do.” — Shawn

3) “One should eschew
The shoe that’s new
And wear it out
Through sun and salt
From Maine to Spain
And back again.” — Charles Day

4) “I wish I had some Sperrys.
I wish I had a yacht.
I wish I had a beautiful wife.
But sadly, I do not.

But if I win these Sperrys,
I’ll sail around the world.
And I hope to find and someday wed
A beautiful island girl.” — Luke

* * *

For our latest Battle of the Wits giveaway, Sperry Top-Sider has generously donated four pairs of the new 75th anniversary edition of its classic Canvas Vulcanized Oxford sneaker. It even comes in a cool replica of the original 1935 box.

The shoe, priced at $75, comes in your choice of white, navy or Nantucket Red.

In the spirit of the CVO’s nautical heritage, here’s the question:

You’ve got a fresh pair of Sperrys, and your custom yacht with the walls lined in blue oxford cloth is ready to set sail anywhere in the world. Where do you go, and why?

Use the leave-comment feature to regale us with your inspiring and creative trip to the ends of the Earth, in 25 words or less.

The usual honor-code rules apply: One entry per household, US residents only. Contest closes Wednesday at 5 PM Eastern Standard Time. Bon voyage.

111 Comments on "Grab This: Sperry 75th Anniversary Canvas Sneaker"

  1. I’d sail to New York. The Red Sox are coming by sea this time.

  2. I head to Newport, RI. Where I once was ignored, now I am envied; they all wish they had Nantucket Red Sperry’s too!

  3. To the Boothbay lobster boat race with my girlfriend followed by a jaunt to Sea Island for sporting clays and sea kayaking

  4. I would charter off to Greece; where Ralph Lauren khaki shorts worn 2-inches above the knees are embraced.

  5. I’d sail up to Maine where I’d order some $75 lobster, to celebrate and look good with my free Nantucket Red Sperrys, of course.

  6. I’d sail the mediterranean, showboating my sneakers, and demonstrate to France and Italy that American men know how to dress too.

  7. I’m going to Portovenere on the Italian Riviera. I want to wake up one morning to the sight of beautifully colored homes. I want to walk out on the back deck of my Riva Athena. I want to be able to see Italian men in their element. To witness first hand impeccable style and attitude. I’m would I’m sure stumble upon a most peculiar one and invite him back to my yacht for glass after glass of Glenlivet 1959 as we exchanged stories of each others lives on the upper deck as the sun went down and lights were glowing in the streets.

  8. Destination Cote D’ Azur. I would sail up and down the coast from Ventimiglia to St. Tropez, making stops in Monaco for gambling and races.

  9. Further. Because.

  10. I’d sail to Japan with my girlfriend to get some of the amazing clothing that’s not available in America.

  11. Way down in Kokomo. That’s where we want to go.

  12. Off to Barbados with Mount Gay in hand, tacking and jibing until I found land.

  13. popponesset, ma. i want to see if my wife’s family leaves their place there open in the winter. those canvas sneakers would be perfect for sneaking!

  14. Zihuatanejo, because building a boat after years of unjust torment is good, but setting sail in it after my friend Red finds me is great. Style, like happiness, seems dim without friends to share it with. And if not me, Further. Because. deserves it. – Like Pops said about Jazz – if you have to ask you’ll never know.

  15. I would sail into Los Angeles and start helping my fellow Angelenos to find that classic American style that has been abandoned for the monstrous skinny jeans–deep v-neck t-shirt–fedora look.

  16. M.D. Cooley | February 8, 2010 at 4:38 pm |

    I’d follow the trail set forth by Kurt Russle, in “Captain Ron” the greatest maritime film ever created.

  17. My hometown, Honolulu. The long way–around Cape Horn with a stop or two in Brazil. The seas are treacherous, but Sperrys afoot, I’ll manage.

  18. As an economics major I would sail right on back to 1935 in search of lessons the Ivies can’t even teach me.

  19. I would simply sail, enjoying both the complexities and blankness of the ocean, hoping a destination didn’t come soon.

  20. Saba, 20 miles south of St Barths. Grab a mooring off the harbor, come ashore, hike to the top of the volcano before happy hour at Scout’s place, watching the sunset across the Eastern Caribbean.

  21. Off to a vacant island for some much needed relaxation… a place to enjoy my new Sperry’s and properly break them in, walking the beach!

  22. Dry Tortugas. After dodging crab lines and day shapes all morning, nothing beats a dive and a beer while the sun sets over the Keys.

  23. Being a native American descent I would sail the route of Columbus and make peace with the inhabitants I meet while dressed in broad cloth , denim, and docksiders; my dog shoe lace and I bringing gifts of Sperry originals.

  24. I’d set sail to the island of Mauritius with the sounds of Marvin Gaye and Eric Dolphy accompanying me.

  25. Chris Bourasseau | February 8, 2010 at 6:16 pm |

    I’ll sail to St. Tropez, France. I get a lot of inspiration there.

  26. With the wind in my hair, the spray of the sea, and the view of the sunset on the horizon, the trip alone is enough.

  27. I would cash in the yacht and buy myself some clothes, it’s cold out with just sperrys on you know.

    Actually scratch that – Mexico.

  28. I’d take my grandfather to the coasts of Normandy, a place he has not been since June 6th, 1941, but one that he yearns to see again.

  29. I would sail to England and try to find the one woman I ever loved. My one gift to her would be nautical passion.

  30. As far as I can make it until the rum runs out.

  31. Maine, Maine, Maine, Maine and again, Maine

  32. To Nantucket, for a scotch.

  33. I’d sail to New Orleans for Mardi Gras. An after party on the boat would go something like this:

  34. I must down to the seas again, the destination matters not.
    And all I ask’s my custom yacht and free Sperry’s t’keep from fallin’ off.

  35. oops! “leave” not “leaves” up there. i’m leaving behind far too much evidence to be any good at sneaking.

  36. As he is one of my greatest heroes, I’d retrace Captain Joshua Slocum’s pioneering solo circumnavigation of the globe, penning observations along the way.

  37. I would wait until my best friend is back from serving overseas in a few months and go wherever he pleases (probably Australia).

  38. I’d sail where it started, mission… to thank Paul,
    because of him, I stand in the squall.
    No slip, no slide… just Sperry, the Top-side!

  39. Charleston Harbor. I haven’t been able to see my parents since the went below mason dixon, and a school of king mackeral are calling my name.

  40. I’d sail from Bimini to Cuba, with a bottle of Havana Club in one hand, cigar in the other, reciting lines of Hemingway’s-Islands in the Stream.

  41. I’d set sail for “The Bite” in Menemsha, Mass. for the best fried clams on the planet. Summer can’t come fast enough.

  42. I’d sail around the world. 80 days? Not a chance, since I’ll be taking my time.

  43. Tacking through the blue-green waters of Chesapeake with my dad, sweating Heineken in hand, wearing light soles as not to smudge the deck, sharing stories.

  44. I’d sail to Valencia, Spain, to watch the America’s Cup, eat Oranges off the tree and drink good, cheap wine straight out of the bottle.

  45. After yacht has been made homey,
    I sit on deck with Dark n’ Stormy,
    Viewing Bermuda afar,
    Til I’m done and off to the bar!

  46. I’d start off in Norwalk, CT a little over half an hour from home but definitely one of the nicer spots to cast off (I used to row crew there in high school). Some easy sailing Northeast through the Long Island Sound and up around Martha’s Vineyard and Nantucket. All the while fishing and feasting on whatever the local game is and whatever spirits I’ve decided to keep on board. Then I’d make my way down to Montauk, maybe dock there since I’ve never been to that side of the island. After a day or so in the Block Island sound, I’d head back into the Long Island Sound, and into Greenwich since it’s only 5 minutes from my house.

  47. Tour the major ports of American history starting in Boston and ending in New Orleans, from revolution and Civil War to modern triumph and tragedy.

  48. I’d anchor down in the San Francisco Bay. There are some of the best, most difficult winds there.

  49. Take my dad to his favorite place on earth, Shelter Island. He taught me to sail, introduced me to Sperry’s, and told me, “Mt. Gay and Tonic needs two slices of lime.”

  50. Punta Eugenia of Baja, from Northern California just to see if I could do it, then back to San Diego for the pleasure of it.

  51. Step 1: Call up the professor. Step 2: Rig up the ship with 121 Jigawatts of juice. Step 3: Sail back in time to early 60s Hyannis Port and kick it with the Kennedys.

  52. Jordan Winer | February 9, 2010 at 12:37 am |

    There’s an island in Greece, very small. It was twenty years ago. Don’t know if she’s still there. Know the water’s still that blue.

  53. Off to an uncharted island south of the Caribbean; a bottle of red wine, some black ray-bans, and John Coltrane.

  54. Jonathan Deng | February 9, 2010 at 4:42 am |

    Headed South—and 60 years back. Hemingway’s Cuba. Frayed khakis, tying up. Blackened flying fish, dusky girls in the waves, sugarcane rum, blankets topside. Sunset.

  55. I’d sail back to Brussels, where my family lives…
    I would go via the Dutch kanals though…
    Thanks to mySperry

  56. ron thompson | February 9, 2010 at 6:06 am |

    Hope Town on Elbow Key. This is the first place I ventured without my parents. I remember scraping together enough money to buy my first pair of Sperry Top-Siders. If you didn’t own a pair in 1985 you were cast off as a landlubber.

  57. ‘Once Was a Man in His Yacht

    Off To Tie The Knot

    In Sneakers by Sperry

    Hoping to Marry

    But, Alas the Ring He Forgot!

  58. Sail from Tampa to Harbor Island off Eulethera in Bahamas. Stay at Coral Sands Hotel, dine at Angela’s Starfish Restaurant, enjoy the steel drum band.

  59. Leave US via Barataria Bay. Few nights of scary solitude on the Gulf.

    Port of Call: Tampico. Blend in with the other gringo expats. Disappear.

  60. the passenger | February 9, 2010 at 8:21 am |

    Assuming money is no object, across the Atlantic to kill a couple of years in various ports on the Mediterranean Sea.

  61. In circles. The 18yr old scotch is flowing is continuously flowing and the Sperry’s are the only thing keeping me topside.

  62. Leaving the snooty behind at Newport, I would cross the Atlantic to drink champagne with my favorite Parisienne under moonlight, a beautiful française named Cécile.

  63. I’d sail Cape Cod and the islands all summer long in my new Sperry CVO’s.

  64. Set sail via NY Harbor down the east coast on an extended vacation to the Florida Keys. Once in the Keys, piss on the same wall as Hemingway, and fish from dawn till dusk. Why? Because Hemingway knew exactly where to take a leak.

  65. Down and around to the cape of good hope. Probably one of the most beautiful places I have ever been. Me, a guitar, music, sperrys, some khakis and a few old oxfords. And, of course, a fully stocked bar and a humidor of cubans.

  66. Take me to the Gold Coast Region of Costa Rica–to howl with Howler Monkeys, drink Mount Gay, navigate Pacific Waters, and embrace western sunsets.

  67. My budget is spare

    As this verse, which I hope will win

    A pair of Sperrys to wear under sail

    Back to where

    I met you.

  68. Like Homer’s Odysseus, I’d travel from Troy to Ithaca. Hopefully my snazzy Nantucket Red Sperries will ward away Scylla and Charybdis!

  69. I just wouldn’t stop sailing.

  70. I go nowhere. I spend the day sprawled on the deck—thinking and relaxing. By going nowhere I’ve gone everywhere.

  71. A Texas Boy without the fortunes to venture through open water. My journey is by the decision of wind & water. Bon Voyage.

  72. Parker Gilbert | February 9, 2010 at 10:47 am |

    I’d sail to Cuba and show them off to Fidel. He has a great backhand, you know.

  73. I would “set sail on this new sea because there is knowledge to be gained.”

  74. “…away from the things of man.”

  75. My yacht and I would sail from New Orleans to Hyannis Port and let them bask in the glory of a well dressed Who Dat. (25 words)

  76. Wherever my love wanted. Many men say they’d go to the ends of the Earth for a good woman. Too few actually do.

  77. I would sail to the Croatian coast, hop islands, and explore the rest of the Mediterranean coastline with my dog.

  78. I would sail to the moon and back…

  79. i’d sail straight into the bermuda triangle to see if i can solve that mystery. and who knows maybe i’d even unlock some other secrets like: why do these sperry’s look so good on my feet?!

  80. I’d sail to Ireland, no contest. Red Sperry’s stained indigo would look great between Oscar and Eduard Wilde.

  81. I’d go to Nantucket, sporting my nantucket red sperrys of course.

  82. I wish I had some Sperrys.
    I wish I had a yacht.
    I wish I had a beautiful wife.
    But sadly, I do not.

    But if I win these Sperrys,
    I’ll sail around the world.
    And I hope to find and someday wed
    A beautiful island girl.

  83. I’d sail to Hyannisport. Once there, I’d climb into my dinghy dressed in khaki shorts, OCBD, and topsiders. My co-conspiritors and I would sneak ashore at the Kennedy compound, play a few downs of touch football on their beach, take a photo, and high-tail it out of there before security arrived. Back on the yacht, we’d toast the Kennedy clan and be better men for having retraced their footsteps.

  84. I would change my name to Desmond and try to crash on The Island from Lost. You never see their shoes on that show!

  85. Anywhere my mother and father wished. They wanted a cruise honeymoon; they had my sister instead.

  86. Jason Rowley | February 9, 2010 at 3:43 pm |

    I’d sail to Greece to visit my family. However, I’d go the long route: first to Japan, where they do American workwear better than American firms, then to India for some madras cloth shirts and outrageously delicious food, then perhaps to Cape Town and finally around the northwest bit of the African continent, through the Straits of Gibraltar, to the Greek isles.

  87. Charles Day | February 9, 2010 at 5:39 pm |

    One should eschew
    The shoe that’s new
    And wear it out
    Through sun and salt
    From Maine to Spain
    And back again

  88. Pick up my girl in Bar Harbor, then down to the Vineyard to propose. Marry on Cumberland Island, Georgia. Set sail for our Bahaman honeymoon.

  89. There once was a student who tarries
    Who won a pair of white Sperrys,
    He want to set sail
    To Harvard or Yale,
    But somehow ended up in the Prairies.

  90. Greg Armistead | February 9, 2010 at 7:31 pm |

    To Madaket Harbor in Nantucket, skip along cobblestone downtown, be admitted to the yacht club for having classic footwear. Fake it till you make it.

  91. One Pair of Sperrys + One Yacht + One World + One Great Woman = One Great Time

  92. I would sail along the West Coast, starting from San Francisco (where I live).

  93. I remember one sunset while on a Coast Guard cutter. The ocean seemed coated with oils reflecting blues, greens, purples. I’d head into the sunset.

  94. I’d Shanghai my sweetie from snowbound Manhattan;
    and sail southeast to Hamilton.
    The three points of our Bermuda triangle:
    White Sperrys, pink sand, black rum.

  95. Haiti, with food and water to drop off. Because I could. Then slowly back up the East Coast, taking pictures, happy to be alive.

  96. No better place to view the panorama of San Remo than from the sea. Then, I’m taking in the jazz festival for a re-enactment of :

  97. My two young sons at my side, I sail in the direction of Gatsby’s green light, reminding them that life is short: go for it now.

  98. I would head over to the depths of the far east and mix the styles of east coast prep and Ivy with the far east colors and classics.

  99. I’d sail to my old dean of students house, and pinch a load on the windshield of his car.

  100. I would set sail to the beautiful Marina Village in San Diego. Just inside the Mission Bay Channel and only minutes from the sparkling open waters of the Pacific, peaceful parkland setting that is surrounded by waterfront resorts and recreational splendor.

  101. To Lorne, on the southern coast of Australia, because she was not with me the first time, but she would be this time.

  102. My destination would be Garden Key, a tiny island 60 miles off of Key West on which is an old Union fort from the civil war sits.

  103. I would sale to Naples and live la dolce vita; a trip to Rubinacci to get fitted for a natural-shoulder tweed jacket followed by fresh oysters and the smell of salt air and lemons as the sun sinks below the horizon over the Bay.

  104. I would sail back and forth between Charleston and Savannah… and sip some bourbon at every stop.

  105. James Schilling | February 10, 2010 at 2:41 pm |

    St. Lawrence Seaway to Lake St. Clair, docking at the Little Club to put up my by now weathered sneakers and enjoy a hummer.

  106. I would sail to the Florida Keys and visit Ernest Hemingway’s house.

  107. Hey, now: Luke’s entry doesn’t come under the 25-word limit. Oh, well: I suppose I’m just bitter, having lost each and every contest so far. Perhaps the gods will strike me with inspiration for the next one!

  108. Interesting that David’s grandfather should have been in Normandy exactly three years before D-Day. Why exactly is that date special for him?

  109. Andrew Adams | February 16, 2010 at 1:14 am |

    I sail through a sea of lost opportunities and never-experienced destinations to place I ache to return but never can. The waves crash against the bow and water splashes onto my canvas Sperrys, the wind catching my navy polo and khaki chinos. I look toward the visage of the past I know I’ll never sway towards, but somehow find solace in the fact that; previously, now, and in the future- there will almost assuredly be a timelessness to what I wear and the way the waves rock me back and forth- and in that fleeting moment of discovery time holds no prisoner. And all is alright. And the destination doesn’t matter anymore. It’s the journey that brings life and purpose.

    I’m young, I live in and was born and raised in mainland Texas; and have never been on a boat. But I don’t need one to know what I want or where I want to go- wherever I find true mystique. That implacable quality of mystery. It is, after all, the curiousity of what comes next that makes the ride enjoyable.

  110. I’d start in Cape Cod for lobster and boogie boarding with my father. We would then sail to Croatia, where our ancestors are from, enjoy our time on the beach and learn about our Ancestry, then to Greece, Italy, and then enjoy a trip down Australia. Hang with the Aussies, bond, and forget about boring Southern Illinois, with it’s terrible weather, and bland landscape.

  111. I would leave the Big Apple with my girl, headed straight for Florida to see her family which she talks about every day. And then get lost in the Caribbean.

Leave a comment

Your email address will not be published.


%d bloggers like this: