It can be difficult when deciding what to wear for school pictures. That one look, on one particular day, will be immortalized forever and in every person's yearbook that year. If a person wore the same outfit for 5 years in a row by change, then from every year on, wearing the same outfit again and again would only become more comical!
I think this is a fantastic idea! How fun would it be to look back over 40 years of photos and see how much you have changed, all while wearing the same outfit? Obviously it takes a person with a great sense of humor, but this is a great story to show and tell.
While initially the idea of wearing the same outfit a picture for forty years seems simple, there are too many variable factors to give an unqualified yes as an answer. What if the person in question gains weight? What if articles of clothing or accessories are lost over the years? What if the school dress code policy for teachers does not allow the particular outfit or aspects of it? Mentally a person may be able to commit to wearing the same outfit for a picture for many years, but giving an unqualified yes doesn't make sense.
A retiring teacher unexpectedly went viral when it was revealed that he had worn the same outfit in his yearbook photo every year for 40 years straight. It's an incredible feat, but one that I definitely couldn't accomplish. I like following trends and having variety in my wardrobe, so while I take my hat off to that teacher's disco look, I acknowledge that our styles are quite different.