Sperry® Gold Cup Top-Siders

These classic men's Top-Sider boat shoes offer orthopedic comfort.


Get excellent siped-sole grip—even in the wettest conditions—in handsome, handsewn, genuine leather Top-Siders. A supple deerskin lining and EVA cushion midsole, along with triple-density footbed and memory foam, provide all-day comfort. Nonmarking outsole. 18K-gold-plated eyelets resist corrosion in salty conditions at sea. Men's Top-Sider boat shoes in cognac.
US whole and half sizes: 8-12, 13.


Overall: 4.6/5 starsShow Rating Distribution 4.6 / 5 based on 15 reviews

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13 of 15 reviewers would recommend this product to a friend.

  • 5/5 stars 5/5

    Gold Cup - 3/17/2014

    ExcelIent! I spoke with wonderful people and bought a pair of great shoes.

  • 5/5 stars 5/5


  • 5/5 stars 5/5

    very comfortable shoe - 7/9/2013

    this shoe out of the box is a very comfortable shoe. I recieved the shoes the day before my trip. this was the only pair of shoes I took on a four day trip with no regrets. Fantastic shoes. you can not go wrong with shoe

  • 5/5 stars 5/5

    Excellent boat shoes - 5/1/2013
    By: from Florida

    I have own dozens of boat shoes of all brands over the years but as of yet none have met the standard of quality of these shoes. From the moment you first put them on they are extremely comfortable. Their design is performance driven and aesthetically worthy of Country club wear. Well worth the high end price.

  • 5/5 stars 5/5

    Gold Cups rock! - 6/11/2012
    By: from Sacramento, CA

    Sperry Gold Cups, at least the three eyelet and two eyelet boat shoes like these, are near perfect. While they are more expensive than lesser boat shoes, they are worth every penny. Gold Cups are lined and cushioned to make them much more comforable than lesser boat shoes -- suitable for walking on hard pavement all day. This is my third pair of Gold Cups, and the others are nowhere near wearing out. My aging feet love them.

  • 5/5 stars 5/5

    Most confortable shoe. - 6/4/2012
    By: from Texas

    Truly like this shoe. very confrtable, fit well and worth the $.

  • 5/5 stars 5/5

    Topsiders - every home should have a pair - 6/3/2012
    By: from England
    Top 1000 Contributor

    Excellent colour and classic boat-shoe design. The deerskin lining and with all the cushioning, make these shoes the most comfortable I have had. I hope this shoe is on re-order with ORVIS UK? Please note: shoe width is medium 'M' as this is not stated in the details.

  • 5/5 stars 5/5

    Great Shoes - 4/30/2012
    By: from Chicago
    Top 250 Contributor

    As has become the expected this purchase exceeded my expectations. Stylish, high quality, and unbelievable comfort right out of the box.

  • 2/5 stars 2/5

    Not the same as they once were - 4/19/2012
    By: from Madison, WI

    I purchased the Gold Cup Top-Siders a few years back and fell in love with them. Both comfortable and stylish. Given that I wear them all the time and they are starting to show their age. Because of that I can't wear everywhere I once did and ordered a new pair. Right when I opened them I could tell they had taken cost out of them to save money. The new Sperry sole does not match up to the old Vibram sole. They also changed the stitching to a darker color… again I preferred the past stitching. The overall color of the leather was also darker. I understand that there will always be a degree of variability to leather but this was much darker and not what I was expecting. I ended up returning the shoes, so I can’t speak beyond my comparisons. If I didn’t have the older pair I probably would have found the shoes acceptable and enjoyed them.

  • 2/5 stars 2/5

    Soles Detached - 4/18/2012
    By: from Atlanta, GA

    I had these shoes (in chocolate) for less than two years before the soles detached from the leather uppers. I only wore them seasonally and have no explanation for the detached soles other than a workmanship defect. Prior to that I loved them, but they cost far too much to last less than two years. Sperry's customer service did nothing other than direct me to a website that wanted $50+ to resole them.

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  • Sperry® Gold Cup Docksider £149.00
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