The ushers’ gift can easily be misunderstood. “Do I have to give one?” “When should I give it?” “What about the ring bearer?" "Aren’t we going a little overboard here?”
Giving gifts shouldn’t be a chore; it should be a pleasure. If someone goes out of his way for you, you should show a little appreciation for the effort by offering the person a gift. An usher may attend several prewedding parties, travel to be with you, rent a tuxedo to look the way you want him to look, go to a bachelor party, give up at least one full weekend for you, and make an effort to make sure people at the reception are having a good time.
The gift -- a small one -- doesn’t have to be elaborate or very expensive. It should simply say, “Thank you for being here for me.” It may be a nice pen, or a money clip, or a leather wallet.
Gifts can be given at a number of different points during the wedding preparation. The best time is at the bachelor party, if there is one. Not only can the groom give the gift, he can say something to the group at the same time. Other times to give the gift to the ushers would be just after the rehearsal the day before the wedding or at the rehearsal dinner.
As for the ring bearer, there's no rule that says you have to give him a gift; however, a small gift is a nice token. Having that little bit of attention that comes from you taking a few minutes to give him a gift will make the event very special and memorable for him. Maybe it’s a fun book (check with his mom for what he might like) or a pair of tickets to the circus and a promise to take him after you come home from the honeymoon.