Here are some of my favorite ideas for a retirement gift for a male boss. When choosing a gift what you buy will depend on how well you know the retiree and how much money you have to spend. Often at work there will be a collection were most people in the office or workplace will contribute. In this case I think a nice gourmet food hamper looks good and generous at a retirement party presentation, also you might consider a more personalized item like an engraved watch.