Men's Authentic Original Tailored Boat Shoe by Sperry

$ 49.99 $ 84.95
1 review   |  

Additional discounts do not apply to this product.

Orders placed before 4pm ET ship same day.
Color: Navy and Red Plaid

The perfect casual shoe for fall! Don these preppy and fun shoes to your next special occasion and you'll be walking into the party like you're walking on to a yacht. You don't need to own a sailboat or a summer home in The Hamptons to be a preppy style icon. Simply pair these shoes with your favorite khakis and classic button down for a timeless look in no time (extra points for a blazer or sweater tied about the neck).

A fun new twist on the classic Sperrys you know and love. These timeless shoes, featuring Ortholite cushioning, full grain leather, and a non-marking rubber outsole will only get better with time. The simple style and classic color scheme will pair well with a wide variety of pieces in your closet, making these your new go-to shoes. Pick a pair up today for yourself, or as a great gift for the preppy men in your life. 

  • Plaid Textile Upper
  • Full Grain Leather Collars
  • Rawhide Laces
  • 360° Lacing System™
  • Ortholite® Cushioning
  • Non-Marking Rubber Outsole 
  • Razor-Cut Wave-Siping™


  • Fun twist on a classic shoe
  • Easily dresses up or down
  • Pairs well with jeans, khakis, or shorts

Shipping Options
All orders ship for free via USPS First Class Shipping (4-5 day delivery). Orders $150+ ship for free via USPS Priority Shipping (2-3 day delivery). UPS Next Day Air shipping is available for $35, but is not available on Fridays or Saturdays.

Returns Policy
View the full return policy in this link. Final Sale items are not eligible for return, exchange, or store credit. All items must be unworn, unwashed, and in the original condition. All returned items must meet the Return Deadlines listed below. Items received by our Return Department that do not meet the criteria listed on the Return Slip will not accepted or processed. Customers are responsible for return shipping. Country Club Prep will pay once to ship an exchanged item back to customer.

Return Deadlines
Refunds: Items must be received within 45 days of the original order date. Refunds will be applied to the original form of payment only. Please allow 2 weeks after your return is processed for the refund to show in your bank account. Shipping fees are not refundable. If original form of payment is unavailable, a CCP Store Credit will be issued.

Exchanges: Items must be received within 60 days of the original order date. All exchanges must be of equal or lesser value. CCP Store Credit: Items much be received within 90 days of the original order date.


Let’s lay out the facts. You’re here either because you’re preppy, you know someone who’s preppy, or you heard how incredibly handsome, sophisticated, and witty we are. As a betting institution, CCP has its money on the first option (and/or the third).

You’re in the right place. Country Club Prep’s mission in business and in life is to find the best preppy designers out there and to bring them to you under one metaphorical roof. Think of us as Zappos for preppy clothing.

When you’re looking for something preppy - ANYTHING PREPPY - visit CCP first. It’s our job to carry that item, but if we don’t, guess what - we’ll tell you where to find it. Your complete satisfaction is just that important to us.

If you’ve browsed the website, then you already know - there’s a veritable cornucopia of reasons to buy your preppy products from CCP. Incredible selection from incredible designers? Check. Unrivaled membership rewards? Double check. Outstanding customer service and an overriding desire to give you the best possible shopping experience? Triple check (so many preppy pink and green checks...).

We’re adding new designers and products to CCP every day. Literally. If there’s a designer that you love that we don’t currently carry, let us know. Send us an email at customerservice [at] countryclubprep [dot] com. If it’s a good fit, we’ll make it happen.

For that matter, feel free to contact us for any reason (not involving manual labor). We’re happy to help, and we’re always eager to show you why preppy has a home.

Country Club Prep
Est. 2012