Repair or Replace – 8 Year Old Sperry Boat Shoes Repair Process

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For reference, I am 6’4 usually 170lb. Typical sizes of clothing:
T-shirts: S
Long sleeve shirts/button downs: M
Dress Shirts: 15.5 x 35
Pants: 30 x 34
Dress Shoes: 12

This video is not sponsored. Contains Affiliate Links.

50 Comments

  1. Philip Cousin on June 17, 2020 at 6:58 am

    Your Sperrys look great!

  2. Daniel Pati on June 17, 2020 at 7:03 am

    👍🏃‍♂️🗽

  3. Christmas Horse on June 17, 2020 at 7:04 am

    You can buy a pair of Sperry Gold Cup boat shoes brand new on sale for around $80. They are an upgraded version of the standard Sperry boat shoe, featuring better insoles, a more comfortable lining, and higher quality leather.

    I understood why you chose to repair this, but I left this comment for anyone interested in Sperry shoes.

  4. Daniel on June 17, 2020 at 7:07 am

    What color are those!?!?

  5. thejasonbischoff on June 17, 2020 at 7:07 am

    Congrats, you just saved a cow.

  6. MrEntourage101 on June 17, 2020 at 7:07 am

    $65 to repair might be a good deal, but you can find Sperry’s at Macy’s for about $65-$70 when using coupons, so def not worth repairing.

  7. Stev Rex on June 17, 2020 at 7:08 am

    My parents promised me their first new car. Which just happened to be a 1962 Impala SS. Which is now considered a classic!

    I always get my shoes repaired.

  8. marco belli on June 17, 2020 at 7:09 am

    Repairing is the BEST 👌👌👌👌

  9. XGenBoomer on June 17, 2020 at 7:09 am

    I’ve been following Bob Powers, Kirby Allison and Daddyos Reviews on shoes.. There’s always room for more..
    Hey, I had my velocity suit from MOS today.. I got a lot of compliments.. I even beat a ticket in court today and got compliments from the court clerk.. Check out my IG @fokonaso 😎Your reviews are paying off.. Thanks! BTW.. Loving that band collar! ✌🏿

  10. AJ on June 17, 2020 at 7:10 am

    Now this is a lifestyle.

  11. Nathan Sukonik on June 17, 2020 at 7:10 am

    Great video might want to this with older pair of ecco high top sneakers 😀 curious what the process is like for high tops leather sneakers.

  12. Vinnie Daniels on June 17, 2020 at 7:11 am

    What a novel idea, especially if you have a favorite pair of unique shoes that can’t be replaced. I’ve had shoes re-soled before and definitely worth the money… Thanks for sharing.

  13. gsotoaz on June 17, 2020 at 7:11 am

    dude it’s cheaper to just buy new shoes

  14. Herb D on June 17, 2020 at 7:12 am

    if u ever decide to replace consider the Timberland 3 eyelet Lug Sole. i wear mine probably twice as as many miles / time as u put on the Sperrys and i’ve never worn out a sole. upper are good for a decade with the similar rare saddle-soaping. might last longer if i didn’t from time to time abuse them in a restaurant kitchen. also generally available as 2nds at the outlet store, Cheers

  15. Sjef on June 17, 2020 at 7:12 am

    How much does the cobbler charge for shortening a leather belt?

  16. ratski robo on June 17, 2020 at 7:13 am

    That Repairman Papa is a sweet endearing man like other gentlemen cobblers. I wish theres more like him and their likes dont disappear.

  17. Randy Milano on June 17, 2020 at 7:17 am

    I’m kicking myself. I just finally chucked my 10 year old boat shoes that I thought were dead after sperry said nothing could be done. Why I didn’t try a cobbler first is beyond me. Yours look great. This is a good lesson in always asking an artisan first before you give up hope.

  18. Flynn Bennet on June 17, 2020 at 7:19 am

    I just got a new pair of sperrys for 85 off their website. Not to much money

  19. Gentleman's Gazette on June 17, 2020 at 7:20 am

    Nice.

  20. Robinson Mertilus on June 17, 2020 at 7:22 am

    Neat. Would have been cool if he let you record some of the process. Maybe to promote his location as a trade off.

  21. Adrian Garcia on June 17, 2020 at 7:22 am

    Why do people like sperrys

  22. Style DAD on June 17, 2020 at 7:22 am

    LOVE IT!!! The Cobbler was so great- totally old school guy. I totally appreciate your take on this. Less waste, supporting a real craftsman, etc. Great video!!!

  23. Corey Newcomb on June 17, 2020 at 7:23 am

    What is the picture on the wall behind you?

  24. Alex 1611 on June 17, 2020 at 7:24 am

    Where’s that shirt from you’re wearing at the end?

  25. Trenton & Heath on June 17, 2020 at 7:24 am

    Great video! We receive quite a few boat shoes into our shop this time of year. Some have DEFINITELY seen their better days, but when you love a pair of shoes, it’s hard to let them go; especially when they can be repaired for less. 👍🏻👍🏻

  26. thejasonbischoff on June 17, 2020 at 7:24 am

    FYI, you can sharpen knives as well. They shouldn’t be thrown out.

  27. marco belli on June 17, 2020 at 7:25 am

    Very nice 👌👌👌👌👌

  28. George Bulbakwa on June 17, 2020 at 7:25 am

    I agree with you with going for repair rather than replace for most things but with Sperry boat shoes, I just replace them. The reason being that I live less than 20 km from one of the factories they contracted to make those. Shoes are made there then the identifying labels are added elsewhere. The overruns of the factory with no labels cost the equivalent of 5 to 8 USD. Those aren’t poor quality runs, just the padding they do to meet quotas in case of emergencies. All the quality of a standard Sperry boat shoe without the labels and for under 10 USD.

  29. Ej M on June 17, 2020 at 7:26 am

    I think that this was a truly encouraging post. This has been my standard belief with footwear, I have always taken my shoes to "my shoe guy " since I was like 22… I have a pair of ferragamo boots that I lusted over for a couple of years and finally broke down and bought them & have repaired & replaced the sole at least 4 times over the past 15 years. …. or even more.

  30. Brady Begeman on June 17, 2020 at 7:26 am

    Do you watch Bedo’s Leatherworks perchance? If you like the art of cobbling and shoe restoration you might check him out. Steve is an artist.

  31. Greg T on June 17, 2020 at 7:30 am

    Love cobblers. But … Sperry Topsiders are designed for walking on wooden boat decks, not for sidewalks or everyday wear unless you want to kill your feet. Certainly the new Vibram sole will last longer than the original, but I would have preferred to find a different pair of shoes to repair.

  32. Khánh Vũ on June 17, 2020 at 7:31 am

    Damn, the cobbler at my area charge at least 100$ to resolve and it can reach much more if I want to get a leather sole.

  33. spotsill on June 17, 2020 at 7:33 am

    You got a bargain where I live it’s $65 for a half soul .

  34. Bigliss90 on June 17, 2020 at 7:34 am

    Do you still have these shoes? How are the outsoles holding up? With the new leather insoles, are these more comfortable than when you first got them?

  35. Steve A on June 17, 2020 at 7:35 am

    BUT !!!!!!!!!!!!
    That new top of the line sole isn’t the original squeegee insole that gives traction on a boat So if you boat your SOL Just saying

  36. Richard - on June 17, 2020 at 7:36 am

    Do you have a 2019 shoe collection video?

  37. felix121984 on June 17, 2020 at 7:36 am

    My feet will always smell better than yours and I dont wear need GEkks.

  38. stefano giovannini on June 17, 2020 at 7:37 am

    will the new sole last longer than the original? Was it glued or stitched? Could these be resoled another time?

  39. friendlygoz on June 17, 2020 at 7:38 am

    Great move to repair. I’ve gone completely to used and vintage shoes. Vintage Florsheim, for example, is better than $1k shoes from today’s producers. I taught myself how to rehab them. I haven’t looked back. Just a point of info: a resolve in the Bay Area where I live would be twice that price.

  40. Chris Garner on June 17, 2020 at 7:39 am

    Those look really good after the repair!

  41. GUERREIRO ITALIANO on June 17, 2020 at 7:40 am

    Tome like !

  42. MG Dobreski on June 17, 2020 at 7:42 am

    Where is this cobbler located? I’ve looked EVERYWHERE to get my Sperry’s resoled.

  43. Chiquito on June 17, 2020 at 7:42 am

    They look really good now!!

  44. Don Clemens on June 17, 2020 at 7:43 am

    Great video!

  45. thejasonbischoff on June 17, 2020 at 7:43 am

    I could be wrong but I believe Sebagos last longer. They’re definitely cooler.

  46. thejasonbischoff on June 17, 2020 at 7:44 am

    Americans need to become more resourceful once again. We’re in a shrinking economy. And it always makes sound financial sense.

  47. worstalentscout on June 17, 2020 at 7:44 am

    fantastic cobblers !……i’m from Singapore and cobblers here charge high prices for lousy materials and poor workmanship

  48. Nathan Sukonik on June 17, 2020 at 7:44 am

    Great video Kavalier! You should check out Minas Shoe Repair in NYC, Slice of NY did a special on his business supposedly he does bang up work and can repair nearly any shoe type.

  49. 40 Over Fashion on June 17, 2020 at 7:44 am

    They turned out great!

  50. Kent on June 17, 2020 at 7:47 am

    Good msg in a throw away world!😉

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