Old Lady Costume for the 100th day of School Crafting with Kids Just heard about the Dress Like a 100 Year Old day where elementary school students celebrate their 100 day of school. I found these images seriously disheartening to the point of being sickening, particularly For the 100th day of school, many people choose to dress up as a "100 year old" person, typically wearing clothes associated with older adults like cardigans, scarves, glasses, and sometimes even a cane, Today's school theme was to dress like a older person on the 100th day of school