Photo by Salt Water New England

Thursday, June 30, 2022

Sperry Top-Sider Sneakers

Photo by My Father
For decades, after Paul Sperry in 1935 invented the iconic boat shoe with the "Razor-Siping" sole, no other brand would do.    

I started wearing Sperry Top Siders, cotton duck sneakers and the leather boat shoes, as soon as I could fit into adult sizes.   Growing up around boats on the Connecticut shore, and living a quarter mile from our yacht club and various boat yards, everyone had them.  And given they were made locally, we made annual treks to their factory to buy them directly.  

Quite a bit has changed.  Are Sperrys still part of The Uniform?

Sailing Along the Connecticut Shore - Photo by My Father.


22 comments:

  1. Still love my CVOs, but I haven't worn the leathers since my last pair rotted into the sunset. Too many better alternatives out there today.

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  2. I wish they still made the original canvas model, not a fan of the new CVOs

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    1. They do:https://www.sperry.com/en/unisex-cloud-cvo-deck-sneaker/32431U.html?dwvar_32431U_color=13505708#cgid=men-shoes-casual&start=1

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  3. I love my leather ones. They are a staple in my life.

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  4. I'd would like to be able to wear my canvas Top Siders or any other canvas shoe but my 70 year old feet are terribly uncomfortable in them. Can anyone recommend a sneaker or boat shoe for geezers?

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    1. Keen shoes. Roomy toe box and serious support. Just scroll through their offerings - yes, even their canvas sneakers have the same level of comfort, at least according to their reviews.

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    2. Thanks for the recommendation. Same problem here and finding comfortable canvas shoes has been...challenging.

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    3. I'm in my 40's, and I have always found Sperrys to be too uncomfortable. There are many better options out there.

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  5. I love mine, several canvas pairs and a leather pair. I wear them all spring and summer.

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  6. I wore Sperry for years and was always satisfied, but now that I am a little older and have a little more mileage on my feet Sebago Clovehitches work better for me. Has anyone tried the Dunham Captain model?

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  7. I wear the leather versions all the way into the fall….love them … CLASSIC

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  8. Sperrys may well have declined, but the America's Cup ones are pretty darned good. They are not as good as Kudus, but they are quite good.

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  9. The Sperry Gold Cup originals are really comfortable. They almost feel like slippers. They are much more supportive than the standard, and they don’t have any logos on them which is an added bonus. Only con is that the laces don’t stay tied for more than a few days at a time.

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    1. I double knotted mine (and put first knots on the ends), and they stay put.

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  10. I've become a fan of the Quoddy version.

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  11. I've always had a slight preference for Sebago Docksides over Sperry Topsiders.

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  12. Quality always wins out! I still love mine, and put them through their paces! Cheers!⛵️

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  13. I've worn Sperry for more that 40 years, both leather boat shoes and sneakers. I especially like Gold Cup, and sneakers' styles now have good cushioning -- but I still have and continue to wear the older style leather boat shoes and two pair of original (unisex) sneakers. Timberland boat shoes and Tretorn sneakers also are favorites. Boat shoes, sneakers, or Weejuns work for almost everything. Dressier situations and dressy occasions are fun but no longer occur everyday.

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  14. Used to be a Sperry fan but have a problem with their sizes (I need a men's 7W and not many choices). Gone through Timberland (good), Quoddy (OK) and settled for Sebago Docksides custom... For 'cloth', Musto Dynamic ProII Adapt sailing shoes.

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  15. Dad bought me 2 pair if Sperry Kudus or their ilk (thick waxy water bead off leather) in ‘69 for sailing. One pair for shore. One pair for boat only. Still do the same with sperry canvas clouds. But for leather deck shoes have moved on to USA/Maine made recraftable Rancourt, Quoddy or Oakstreet. All great artisan handcrafted super comfortable deck shoes that stand up well.. Sperry use to make a Kudu chuka boot that was my favorite for fall sailing. Sadly, There is no company making that anymore that I can find with a deck sole.

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  16. Blue Sperry canvas for the boat, Jack Purcells for tennis. Still have mine from my teens. Will NEVER give them up.

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