*2 for $99 offer applies to select marked sale and clearance styles. Use coupon code at checkout. Shipping and taxes are not included in $99.00 price point. Any additional pairs beyond the 2 pair threshold will not be subject to this discount. Free Shipping applies to ground shipping only. Online offer valid until 11:59 PM EDT 8/1/16. © 2016. The Rockport Company, LLC. Rockport ®
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Castleton Wingtip

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Highly shock-absorbent cushioning protects the heel at impact


The Castleton Wingtip is a stylish dress casual shoe that is perfect for casual Fridays at the office or a night out with the guys. This men’s wingtip shoe utilizes full grain leathers that provide a unique and stylish look. In addition, the combination of an EVA footbed and ADIPRENE® by adidas sport technology yield a supremely comfortable casual dress shoe. A detailed leather sole helps provide a design that is sophisticated and easy to dress up or dress down. Style made comfortable from day to night.


  • ADIPRENE® by adidas sport technology for all day comfort with shock absorption in the heel.
  • EVA footbed is lightweight and cushions to help conform to the foot for a personalized fit
  • A leather sole with a rubber walking surface helps provide sophisticated styling, as well as shock absorption, durability, and flexibility
  • Full grain leather is easy to clean and maintain to extend product life


Highly shock-absorbent cushioning protects the heel at impact


Castleton Wingtip is rated 4.5 out of 5 by 10.
Rated 3 out of 5 by from new is not better I have worn out three pair of the old design wingtips Dressports and this one seemed to be the same; however, the rubber sole is not quite half the thickness of the others I bought. In fairness, I have only been able to wear them around the house for a few days but I can already tell they are not as comfortable as the other, no longer available, style shoe in which I could walk all day.. Too bad, as I said, new is not always better. And, the tongue on the right shoe digs into the top of my foot -- maybe just needs b breaking in. Maybe time will tell but I will not take them on a trip where I plan to walk a lot. Will take my last, almost worn out Dressport and hope it continues to last
Date published: 2013-12-24
Rated 4 out of 5 by from Great look and feel Very comfortable walking shoe. Just got back from a "walking vacation" in a couple of big cities. Walked 6 to 8 miles per day in these shoes after only owning them a few weeks. Virtually no break in time. They are delivering the usual great Rockport service. They do tend to run a bit wide which can be an issue if you have narrow feet. They look great with jeans and khakis. 
Date published: 2013-11-10
Rated 5 out of 5 by from Sharp! I purchased these right before Christmas. They look sharp (I bought the blue) and are really comfortable. These are only my second pair of Rockports (the first was a pair of awesome boots), and I continue to be very pleased with the comfort and quality.
Date published: 2014-01-08
Rated 5 out of 5 by from Confortable fit I've bought several pairs of Rock-port shoes in the past and I found them to good fit for my feet and long lasting instead of buying several shoes last they look good nice arch wears well on my feet if I could every pair I buy would be "ROCKPORTS"
Date published: 2014-01-04
Rated 5 out of 5 by from The Perfect Shoe I bought these shoes in brown and liked them so much, I went back and bought black as well.  I had a stroke a few years ago so my feet give me lots of pain; these are the perfect most comfortable shoe I have found...thank you Rockport!!
Date published: 2014-01-03
Rated 5 out of 5 by from Comfort Was worried about buying on line since w wear orthotics in my shoes. However the fit was perfect and they're the most comfortable shoes I now own. I've received many compliments on the style. 
Date published: 2014-01-03
Rated 5 out of 5 by from These are my favorite shoes for now. I was looking for something of classic, but not too classic, very good quality and not over priced. I got exactly what I wanted with this pair. It's my 6th pair with Rockport. 
Date published: 2013-12-20
Rated 3 out of 5 by from Could be more stylish This shoe is very comfortable and upportive for a long day of wearing. A bit disappointed that it doesnt look as good and stylish as in photos
Date published: 2014-01-04
  • 2016-07-28T06:24CST
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