My boys LOVE when their teacher tells them they can dress up like a 100-year-old for the 100th day of school.
Step 1: Clothes & Hair Ideas
Here are just a few clothing ideas for boys and girls to wear and ways to style their hair.
For boys: bowtie, suspenders, button-up shirt, sweater vest, glasses, driving cap, mustache, bushy eyebrows, fake pipe, cane, hair combed to the side, hair combover
For girls: floral dress, house dress, bathrobe, button-up sweater, pearls, glasses with chain, shawl, cane, hair in bun, hair in curlers
Step 2: Makeup
Here is how I do my boys . . .
BEFORE — I spray their hair with gray or white hairspray before I do the makeup. This way I can clean off their hairline, if any color gets on it.
ONE — Add “shadowing”, I just use my finger to smudge some brown eyeshadow under the eyes, on both sides of the chin, along the jawline, and on the temples. Then I rub it in a bit, also with just my finger. (I’m always in a hurry to make sure to get this done before school in the morning. It would probably look a little better if I used a makeup brush, but I sure don’t have time for that. ?) 
TWO — Add eye and eyebrow “wrinkles”, I draw on all their wrinkles with an eyebrow pencil. I add wrinkles under their eye and then have them scrunch their eyebrows together so I can see where their wrinkles are naturally and just draw over those wrinkles. Now add some “crows feet wrinkles” on the outside of their eyes.
THREE — Add the smile line wrinkles. When they smile they have natural lines. So I just take the eyebrow pencil and trace over those lines.
FOUR –Trace in the forehead wrinkles. Raise the eyebrows up dramatically so you can see where all the natural forehead wrinkles are. Trace over those wrinkles with the eyebrow pencil.
FIVE — Color the eyebrows. I spray some of the colored hairspray on a q-tip and paint the eyebrows.
GIRLS — I would definitely add some lipstick and maybe a little mascara.
Step 3: Accessories
Now for accessory options. For me, the “if found, . . .” sign that I pin onto their backs is a must! ?(download below) I put it through my laminator so that it won’t rip through the safety pin during the day, but it is not necessary.
You can just keep it simple, like one of my son’s did and just do the clothes and make-up . . .
OR you can add a few accessories like my other son wanted to do. He wanted glasses, so I took the sunglass lenses out of some of my old aviator sunglasses. He also wanted a mustache, so I stuck on one of these mustaches.
