*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 ®
The E-Mail / Password combination did not match our records. Please try again.
The E-Mail did not match our records. Please try again.
An E-Mail has been sent to your mailbox with your new password.
Sorry, the order information provided was not recognized or incorrect, please try again.

Ledge Hill Wingtip

Item #
Special Offer:


Select Size

Select Width
Ledge Hill Wingtip, , medium Ledge Hill Wingtip, , medium Ledge Hill Wingtip, , medium Ledge Hill Wingtip, , medium
360 view

Highly shock-absorbent cushioning protects the heel at impact


Inspired by classic American design, the Ledge Hill Collection offers a variety of versatile dress shoes and boots appropriate for any occasion. Built with leather and suede uppers, soft canvas linings, and ADIPRENE® by adidas sport technology, you are sure to be comfortable all day. This collection is the perfect combination of style and comfort. Modern business demands versatility and accessories that will go anywhere. Our Ledge Hill Wingtip is both a casual and a dress shoe, offering office to field to weekend functionality.


  • Leather and suede upper materials are easy to clean to extend product life and help provide a clean, casual look
  • EVA footbed conforms to the shape of the foot to help provide a personalized fit
  • Lightweight EVA outsole helps absorb shock to help reduce foot and leg fatigue
  • Last
  • Last developed in Italy with some of the world’s most skilled shoe artisans
  • ADIPRENE® by adidas sport technology for all day comfort with shock absorption in the heel


Highly shock-absorbent cushioning protects the heel at impact


Ledge Hill Wingtip is rated 4.48 out of 5 by 50.
Rated 5 out of 5 by from My goodness - these are comfortable This is the third pair of Ledge Hill shoes that I've bought in the last 6 months and I wear each regularly. I have two pair of wingtips that I rotate for work and one saddle that draws admiring comments, trust me. This latest pair is the tan wingtips. The leather on my pair is a little less "pebbled" than the photo but that's a very minor quibble. They are extremely light, flexible, and simply comfortable from the first wear. After a half-dozen wears, the leather uppers become even more flexible. I have no criticism whatsoever except that they are becoming hard to find. That's why I bought three different pairs - I'm worried that I won't be able to replace them in the future.
Date published: 2014-09-30
Rated 5 out of 5 by from Typical Rockport Purchase For Me Rockports are the most comfortable shoes I own. I choose a style I like of course, starting with the category such as casual or dress, and then pick the style itself. But I wouldn't even consider keeping them if they weren't comfortable. I've bought 5-6 pairs online within the last several months, and they're all perfect. They're light, comfortable and look great. I already have a few other pairs I'd bought in a Rockport store, and in a department store. I obviously keep coming back for more, and recommend them all the time. They are just great shoes all around, and last me literally years.
Date published: 2014-10-11
Rated 5 out of 5 by from They ain't sexy, but... The rare case when comfort truly trumps style; not that they're unattractive, but there is an "old man" aspect according to my girlfriend (which I get). However, they are, far and away, the most comfortable dress shoes I've worn, which is why I wear them to the office every day. I have very wide feet and walk a lot for my commute and while I'm at work, so having an extra wide option was a huge factor in my decision to purchase these. The only major con is that the color scuffs off immediately, and I mean immediately. After the first day of wearing them, it looked like I'd taken a highlighter marker to the toes and heels. The good news is that they look even better after a proper shoe shining than out of the box, so my hope is that they'll continue to age gracefully.
Date published: 2014-09-09
Rated 5 out of 5 by from Excellent shoe, go casual or formal This is a great shoe. Extremely comfortable and lightweight. I have worn it with jeans, khakis , and when in a suit and tie. Many compliments on the look from others. I have always worn this brand for its look and comfort, and this shoe meets all the criteria.
Date published: 2013-05-23
Rated 5 out of 5 by from 3rd time's a charm this is my 3rd pair of rockports. i looked high and low for a great looking pair of wingtips. i'm retired and my wardrobe consists of 21 pairs of jeans and about 50 or so casual shirts. i wanted a pair of wingtips that looked good with my wardrobe. everything i saw was either too dressy or too far out looking for me. these were PERFECT. they look good and they fit good. just like my other 2 pairs. i don't really care for much of what rockport shows but sometimes they come out with a winner. these are winners. (if you shop around you can find them for alot less than $135)
Date published: 2013-03-20
Rated 5 out of 5 by from Perfect casual work shoe I love this shoe. Very comfortable and stylish casual work shoe. I can wear them in nice khakis or jeans. The heel inners are comfy and the soles are cushy. This is my fourth pair of Rockports. I'm currently trying to come up with a reason to buy another pair...a reason that I can "sell" to the wife, that is!
Date published: 2012-12-21
Rated 5 out of 5 by from Very Comfortable and Versatile!!! I was looking for a comfortable casual shoe I could wear daily at work. These are by far the most comfortable business casual shoes I have. Many compliments when I wear them and they pair up with jeans very nicely.
Date published: 2015-01-05
Rated 5 out of 5 by from 1st pair - will buy more Thought about buying Rockport for a while, but never managed to see a pair in my size that I 'wanted'. Was out shopping for a pair of formal/casual brogues (boot or shoe) with a maximum price of $400.  Could not find anything that 'took my fancy'. I had just about given up when my wife spotted these. Tried them on and wow! Comfortable, smart enough for semi formal. Comfortable enough for everyday wear. I walk a lot and like to carry as few pairs of shoes when travelling - these will be ideal. Fit is true to size and I got the wide fit.
Date published: 2013-11-03
  • 2016-07-27T06:23CST
  • bvseo_cps, prod_bvrr, vn_cps_3.3.0
  • cp_1, bvpage1
  • co_hasreviews, tv_2, tr_48
  • loc_en_US, sid_lhwingtip, PRD, sort_relevancy
  • clientName_Rockport