How To Dress Like a 100 Year Old Man #100DaysofSchool

100 Days Smarter!! We LOVE how this transformation of my 1st grader into a 100 year old man turned out. Kyle was SUPER excited about his new look with wrinkles, glasses, and vest. Isn’t he cute?? And truly we did all this in just minutes – it was so easy! Is your school celebrating the 100 Days??? If so, and you need to transform the kidlets, check out our tips on How To Dress Like a 100 Year Old Man for your boys and our tips on how to draw wrinkles.

How to dress like a 100 year old man for the 100 Days of School

Kyle’s wrinkles were the coolest and honestly they made him look utterly EXHAUSTED!  He really looked his age. We kept asking him if he was tired and Kenzie thought he was making dirty faces at her since the wrinkles kind of gave him a permanent scowl. Too funny!

How To Dress Like a 100 Year Old Man for 100 Days of School Celebrations

Here’s a few ideas to get you started on transforming your little elementary student into a 100 year old senior citizen.

1. Gray Hair 

This can be a really easy transformation. We used baby powder and hair spray to give the hair a grayish tint. Then we styled Kyle with a nice little combover!


Glasses, a fancy pen, pocket watch, old fashioned cap, a cane or walker if you have one available to use. Even a wooden walking stick would look great!

3. Draw on Wrinkles 

Super easy to do and this will age your child quickly!

4. Clothing Inspiration

Sweater Vest, Bow Tie, Suit Jacket/Blazer, Dress Coat, Vest, Suspenders, or Wear a Robe 

5. Add facial hair like a mustache or beard.


How to Draw on Wrinkles to Look like a 100 Year Old Man

Totally easy. Just use an eyeliner pencil to draw in wrinkles. Any color like grey, brown, or black works. I used black because that is what we had. If you don’t have eyeliner, using eye shadow would work as well.

First, ask your child to scrunch their face up so you can fill in where the potential wrinkle will someday be located. Remember, beyond just the forehead wrinkles, add in wrinkles around their lips, dimple areas, and the crows feet by their eyes. As you can tell by our photos, these wrinkles aged Kyle fantastically!



About Colleen Padilla

Colleen Padilla, the founder and editor of lives in the Philly suburbs and is a full time mom for her 2 children, Mackenzie (7) and Kyle (5). Colleen and the Classy Mommy website have been featured on Fox News, Good Morning America, The New York Times, Parenting Magazine, The New York Post, local Philadelphia ABC, CBS, and NBC programs. Colleen has appeared in a TV special about Alpha Moms on South Korea’s NBC affiliate SBS. She also co-authored The Digital Mom Handbook (HarperCollins).


  1. Mary Potts says:

    Thank you for this….I am seriously stressed out about this whole 100th day of school dress up! But this sounds easy and I have all of these items! Love the wrinkle idea!

    Looking forward to seeing what my little guy turns out looking like!

  2. Anonymous says:

    How Wonerful

  3. Vocalmama says:

    This is great! My little dude’s 100th day of kindergarten is tomorrow and I was sweating about this one a bit! This are great easy tips. I might just stop at goodwill or the dollar store on the way home from work! Thanks so much!

  4. Christa Spencer says:

    These tips are so amazing, my kid decided last minute to participate. Not so stressed out now. Thanks a ton, he looks adorable. Wish me the same luck!

  5. Tonya pilloni says:

    Thank you!!

  6. Anonymous says:

    needs work

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  10. Jill Vitale-Aussem says:

    I know you don’t mean any harm by posting this and I usually love your blog but this “dress like a 100 year old” trend reinforces negative stereotypes of older adults is harmful to kids and elders and society. I don’t blame you – the activity and this post are just a reflection of the overall negative view of aging in our society. But we have to start changing this and exposing kids to the gifts that come with aging. How about something that honors older people – like “meet a 100 year old day?”

  11. Tiffany Bostwick says:

    I wanted to thank you so much for taking the time to write this down for parents that want to encourage children to participate in school activities!!! My son will definitely be excited about this.

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