Dress shoes can be clunky and uncomfortable for men who are not used to wearing them. To solve this problem, Cole Haan has developed the Lunargrand Wingtip–a shoe that utilizes Nike’s Air technology. This is a very dapper shoe and is extremely comfortable to wear. No longer will have need to worry about your feet hurting after a long day at the office. The shoe is available in black, blue and brown and worth every penny of the $250 price tag.