Size 5.5 Sailing Shoes

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Sperry Top-Sider Angelfish

Sperry Top-Sider Angelfish - Greige/Pink Floral (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Angelfish

Sperry Top-Sider Angelfish - Linen/Oat (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Angelfish

Sperry Top-Sider Angelfish - Rose/Lavender Open Mesh (Women's)
 
$84.95 Free Shipping Both Ways!

Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - Black (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - Black/Mesh (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - Linen/Oat (Women's)
 
$84.95 Free Shipping Both Ways!

Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - Tan (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - White Tumbled (Women's)
 
$84.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bahama 2-Eye Sequins

Sperry Top-Sider Bahama 2-Eye Sequins - Aqua/Pucker Zebra Sequins (Women's)
 
$74.95 Free Shipping Both Ways!

Sperry Top-Sider Bahama 2-Eye Sequins

Sperry Top-Sider Bahama 2-Eye Sequins - Black Sequins (Women's)
 
$74.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bahama 2-Eye Sequins

Sperry Top-Sider Bahama 2-Eye Sequins - Blue Iridescent Sequins (Women's)
 
$74.95 Free Shipping Both Ways!
 
Sperry Top-Sider Bahama 2-Eye Sequins

Sperry Top-Sider Bahama 2-Eye Sequins - Pink/Orange Zebra Sequins (Women's)
 
$74.95 Free Shipping Both Ways!

Sperry Top-Sider Bahama 2-Eye Sequins

Sperry Top-Sider Bahama 2-Eye Sequins - Yellow Jersey Sequins (Women's)
 
$74.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye

Sperry Top-Sider A/O 2-Eye - Aqua/White/Pucker Leather (Women's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye

Sperry Top-Sider A/O 2-Eye - Grey/Yellow Leather (Women's)
 
$89.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye

Sperry Top-Sider A/O 2-Eye - Nude/Blush/Greige Leather (Women's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye

Sperry Top-Sider A/O 2-Eye - Orange/Pink/White Leather (Women's)
 
$89.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye

Sperry Top-Sider A/O 2-Eye - Pink/Green/White Leather (Women's)
 
$89.95 Free Shipping Both Ways!

Sebago Docksides

Sebago Docksides - Brown Elk (Men's)
 
$98.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Saddle Tan (Men's)
 
$98.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Moss Green (Men's)
 
$98.95 Free Shipping Both Ways!

Sperry Top-Sider Bluefish 2-Eye

Sperry Top-Sider Bluefish 2-Eye - Linen/Lavender Gingham (Women's)
 
$89.95 Free Shipping Both Ways!
 
Sebago Spinnaker

Sebago Spinnaker - Navy/Red (Men's)
 
$99.95 Free Shipping Both Ways!
 
Sebago Spinnaker

Sebago Spinnaker - Blue/Brown (Men's)
 
$99.95 Free Shipping Both Ways!

Sebago Spinnaker

Sebago Spinnaker - Navy/Green (Men's)
 
$99.95 Free Shipping Both Ways!
 
Sperry Top-Sider Intrepid 2-Eye

Sperry Top-Sider Intrepid 2-Eye - Linen/Mesh (Women's)
 
$69.95 Free Shipping Both Ways!
 
Sperry Top-Sider Intrepid 2-Eye

Sperry Top-Sider Intrepid 2-Eye - Tan/Mesh (Women's)
 
$69.95 Free Shipping Both Ways!

Sperry Top-Sider A/O 2-Eye Woven

Sperry Top-Sider A/O 2-Eye Woven - Hot Pink/Cognac (Women's)
 
$124.95 Free Shipping Both Ways!
 
Sperry Top-Sider A/O 2-Eye Woven

Sperry Top-Sider A/O 2-Eye Woven - White Woven (Women's)
 
$124.95 Free Shipping Both Ways!
 
Sebago Spinnaker

Sebago Spinnaker - Mocha NuBuck & Tan Waxy (Men's)
 
$104.95 Free Shipping Both Ways!

Sebago Spinnaker

Sebago Spinnaker - Navy/White/Red (Men's)
 
$104.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Blue Nite Full Grain Leather (Women's)
 
$94.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Brown/Blue (Women's)
 
$94.95 Free Shipping Both Ways!

Sebago Docksides

Sebago Docksides - Chocolate (Women's)
 
$94.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Ivory (Women's)
 
$94.95 Free Shipping Both Ways!
 
Sebago Docksides

Sebago Docksides - Ivory/Blue (Women's)
 
$94.95 Free Shipping Both Ways!

Size 5.5 Sailing Shoes

1-36 of 68 results   1 2  Next »
Sperry Top-Sider Bluefish 2-Eye
Womens Sperry Top-Sider Bluefish 2-Eye March 18, 2013
Reviewer: David from Boling, TX
These shoe's were shipped on time as predicted by the website and fit my wife's foot exactly as expected.
Wears this shoe: Work Shoes
Sperry Top-Sider Angelfish
Cute, great for sitting! March 15, 2013
Reviewer: popsitoes from Lake Michigan
Very cute shoe, but a sailing shoe was not built for comfortable walking. Just wish you guys could put a bit more chush into a cute shoe for the land-lubbers.
Wears this shoe: when I need to impress the yachting crowd.
Sperry Top-Sider Bahama 2-Eye Sequins
amazing comfort, and stylish! March 12, 2013
Reviewer: Natalie from United States
I bought these Sperry's because they are super cute, and they are very supportive as well! It is nice to have a comfy shoe that fits great and feels good. These shoes really exceeded my expectations, and I am glad to say that I was very pleased with my purchase!
Wears this shoe: everyday
Sperry Top-Sider A/O 2-Eye
Too cute!! February 20, 2013
Reviewer: Marilyn from Kansas
Let granddaughter pick out Sperrys for 16th birthday gift. Seeing them online I thought they might look kind of matronly for a teenager but far from it!! She is absolutely thrilled with them & so am I. They are adorable! Of course the quality is top notch & the colors are soft & springy looking. She chose the tri-color style, which looked perfect on her. She says they feel great out of the box. Since we now have snow she'll have to wait a while to wear them. Very pleased with these shoes!
Wears this shoe: Granddaughter will be the wearer & she'll wear them everywhere
Sebago Spinnaker
Wonderful shoes, in love with Sebago! January 11, 2013
Reviewer: Josh from New York, NY
I purchased these in navy/lagoon and white/limeade and love the color and fit. I have used these on a regular basis since I purchased them close to a year ago and they are still in great condition. They fit very comfortably and the styles are awesome. They match with so many items you cannot go wrong with this purchase. I am a man and fit a men's size 8 so I added two sizes up to these and purchased a women's size 10, they fit really good. I have slightly wider feet then normal I would say and they were a bit tight on the sides but these stretched within a couple of days of wear and felt comfortable. I only wish they were a bit more flexible in the material out of the box but this is only a minor issue. I will continue to purchase Sebago products for their tremendous quality.
Wears this shoe: Anytime