How long should I wear retainers? Not that many years ago, the recommendation for wearing retainers was to wear them for a few months after orthodontic treatment and that was about it. Well, we know a lot more now than even 10 or 20 years ago and the new recommendation is to anticipate Retainer for Life. We all know that skin sags down and wrinkles form over time. Much in the same way, teeth have a tendency to shift forward and inwards over the course of a person’s lifetime.