Sitewide sale - Up to 90% off everything! All prices as marked, no coupon necessary
Item Code: 14132-129 
Sperry Winsor
This item is currently out of stock.
  • On Sale

Size Chart
Sperry Winsor

Elegant yet sophisticated, The Sperry Winsor is a penny loafer that won't kill your ankles. Genuine hand-sewn construction yields a very wearable, comfortable shoe. A full great leather sock lining allows for sockless wear and a memory foam cushioned bed will have you looking forward to putting them on in the morning. A flexible rubber outsole will move with you instead of staying stiff, with non marking, slip resistant rubber. Get your shiny penny's ready, the Sperry Winsor is here to stay.

  • Leather Upper
  • Memory Foam Cushioned Footbed
  • Flexible rubber outsolee, non-marking with Wave-Siping
Heel Height
  • 1 inch
  • 12 oz.
  • Full Grain Leather Sock Lining
Country of Origin
  • China
Item #
  • 9236233, 9660549

Ratings & Reviews
5 Star
4 Star
3 Star
2 Star
1 Star
  • Size: 66.67% True to Size (3 ratings)
    • 66.67% True to Size
    • 33.33% Runs 1/2 Size Small
  • Width: 100.00% True to Width (2 ratings)
    • 100.00% True to Width
  • Arch Support: 50.00% Excellent (2 ratings)
    • 50.00% Excellent
    • 50.00% Good
Show all Reviews
Your Reviews
Write a review, others want your opinion.
Click here to begin your review...
By:Julie Verified Purchase   November 04, 2013
Order true to size
Very stylish, great support. Based on reviews, I ordered a 1/2 size larger...not necessary. Even with gel inserts and socks, they were too big as they are leather and will stretch.
Was this helpful?
Write a comment here...
By:JANET Verified Purchase   March 11, 2013
Oooh..The Cordovan is perfect.
I LOVE the Cordovan color, very rich. The lug sole is a nice touch; you aren't going to find it around a lot and gone are the days of having no traction. I will say that the lug sole makes the shoe more casual and if you like hearing the sound of your penny loafers on hardwood floors, then these aren't for you. I rated it Runs 1/2 size small because if you have a wider foot I'm a C/D normally, but I have very small heel and ankle so I can wear a M/B size if I go up a 1/2 size. Some will argue against this, but I've never regretted it and yes, I can walk in them. And they are from Sperry, a company that's been around a long time. Love their top-siders, as well. Am definitely going to buy the black patent in the Winsor. These are very well-crafted loafers and what can I say...I'm a sucker for Cordovan!!!
Was this helpful?
Write a comment here...
By:cynthia Verified Purchase   November 09, 2012
Love these
I really love these shoes, they are very comfortable, and some people have written to order a half size larger, but I believe I order all of my shoes a half size larger for thicker socks. They are very stylish and go with anything.
Was this helpful?
Write a comment here...
Questions & Answers
Got a question? Somebody out there has the answer.
Click here to ask about this product (e.g. Is it true to size?)
  • Your Name :
  • Your Email :
  • Friends' Email :

Enter one or more email addresses, separated by a comma,
or enter addresses from your email address book!

We Need To Make Sure You're A Real Person!
Please Type the Characters You See Above

Your E-Mail address?
Do you have a Planet password?
    Secure Sign In
    I forgot my password.