Retirement is a special time in a person's life when the focus is off of work, schedules and stress and on the individual. Because retirement is usually a relief for the retiree, it's an appropriate time to poke fun at his good fortune. Show the retiree you appreciate her with a gift, but be playful and make fun of her new lifestyle.
Perhaps the most obvious difference between the world of workers and retirees is that retirees don't work. Many funny gift options take this idea to the extreme. For example, give a pair of dice that will help the retiree decide what to do. The dice are printed with activities such as "Play golf," "Take a nap" and "Go fishing." Some of these dice also sold in jumbo sizes, which reminds us that eyesight is usually the first thing to go.
Alternatively, buy or make the a retirement checklist. This is funniest if the list is long but filled with frivolous activities like "Don't go to work," "Count pills" or "Oil the rocking chair." Remind the retiree her life may be just as busy as when she was working after all but it will be on her terms.
A funny gag gift for someone retiring from the construction business is yellow caution tape, orange cones and construction signs that read "Slow down - no work zone" to reflect the fact that the retiree isn't going to be part of the working world anymore.
The way the new retiree conducts business and handles money may be much different now. For a retired executive or salesman, order business cards but only print the retiree's name and a message like, "I'm retired, so that's all you need to know" or "Don't call me, I'll call you." Tell him these cards will help when networking with other retirees.
If you give gifts that poke fun at how little money some people receive during retirement, the retiree should be in a very secure financial situation, perhaps traveling the world or buying a vacation home in an exotic locale. The gifts are not appropriate for retirees whose financial situation may be questionable.
Many gag gift shops carry very small piggy banks and savings jars with "retirement fund" printed on them. Or make a retirement survival kit. The kit could include things like a shoestring to reflect the kind of budget she will be living on, a tin cup so she can beg for money and a cardboard box to live in.
Silly retirement gifts are appropriate for anyone. Although they may not be functional, they offer entertainment for the gift giver, especially if presented at a party so others can see the silly gift.
A "hearing enhancer" is a large cone that the retiree can put in her ear to better hear people speaking. Usually the cones are printed with "Happy retirement," "Over the hill" and "Super duper acoustic booster" messages. Make or buy a sign for the retiree's car that cautions other drivers. The signs are usually in an attention-grabbing color, like yellow or orange, and have messages like "Retired driver" and "Nowhere to go."
Many gag gift shops sell retiree clocks that have no place for batteries, so the hands do not move. The theory behind this gift is once the retiree supposedly no longer has a strict schedule, she will not need to know what time it is. If you don't want to buy a gag clock you could give a clock that no longer works.