The Hobo Bag
Retire At: 50
As the type of person that likes to be prepared for any situation that might come up, I can relate to this one. I usually always have a backpack or something in the car to carry everything I might need. However, according to most fashion reports the “Giant Hobo Bag” that some women wear as a purse can be a tricky item to pull off. Unless you’re headed out on a potential overnighter and want to be prepared, they recommend that after the age of 50, you should opt for something smaller and more manageable.