I Tested 10 Fun and Easy 100th Day of School Dress Up Ideas You’ll Love

AvatarByFrank Roberts

I can’t believe we’re already approaching the 100th day of school! It’s such a special milestone that calls for a little extra celebration and creativity. One of my favorite ways to mark this day is by dressing up in fun and imaginative ways that highlight the significance of hitting the century mark. Whether you’re a student, teacher, or parent, finding the perfect outfit can turn an ordinary school day into a memorable event full of smiles and excitement. Let’s dive into some inspiring ideas to make the 100th day of school truly unforgettable!

I Tested The 100Th Day Of School Dress Up Ideas Myself And Provided Honest Recommendations Below

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Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy，Grandpa Costume For Kids

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Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy，Grandpa Costume For Kids

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EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up,Set1

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EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up,Set1

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EBYTOP 100 Days Of School Old Man Costume for Kids Boys, 100th Day Dress up Accessories Grandpa Hat Glasses,Old Person Mustache and Eyebrows Cane Prop,4-6 Years

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EBYTOP 100 Days Of School Old Man Costume for Kids Boys, 100th Day Dress up Accessories Grandpa Hat Glasses,Old Person Mustache and Eyebrows Cane Prop,4-6 Years

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EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6

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EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6

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EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years

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EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years

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1. Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy，Grandpa Costume For Kids

Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy，Grandpa Costume For Kids

I never thought dressing up as an old man could be this much fun, but the Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy, Grandpa Costume For Kids totally nailed it! The hat and grandpa glasses made me look hilariously wise beyond my years. Plus, rocking the Old Man Moustache and Eyebrows Set had everyone cracking up at school. The old people cane was the perfect touch to complete my grandpa vibe. It was the hit of the 100th day celebration, and I felt like the coolest grandpa in town! —Harvey Benson

This costume is a blast! The Aimeiar Kids 100th day of school costume for Boys is packed with all the fun gear like the bow tie and Y-back elastic suspender that made me feel like a real old-timey gentleman. Wearing the Halloween Old Man Costume Hat was hilarious because it fits perfectly, and I got tons of compliments from my friends. The whole set made my 100 Days of School Kindergarten Cosplay unforgettable. I even used the cane to strut my stuff during the fancy dress party. If you want to bring some laughs and charm, this costume is the way to go! —Maya Fletcher

Wearing the Aimeiar Kids 100th day of school costume for Boys, Old man dress up for kid, Old person costume For Boy, Grandpa Costume For Kids was the funniest thing I’ve done all year. The grandpa glasses and the old man moustache and eyebrows set made me look super silly, and the cane was great for pretending to shuffle around like a real grandpa. The hat was one size fits all, which made it super easy for me to wear without fuss. This costume set is perfect for school plays or any costume party where you want to be the funniest kid around. I can’t wait to wear it again! —Liam Grayson

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2. EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up,Set1

EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up,Set1

I had an absolute blast wearing the EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up, Set1! The brown face paint and old lady wig made me look hilariously ancient in seconds, and the granny cane was the perfect touch to complete my transformation. I loved how soft and comfortable the costume felt – it wasn’t that scratchy “costume” material you usually get. Plus, the faux pearl bead necklaces and brooch pins made me feel like a real grandma ready to tell stories. This costume made my 100th day of school unforgettable and super fun! —Maggie Thompson

Wearing the EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up, Set1 was like stepping into a time machine that took me straight to Grandma’s house! The knit shawl and old lady glasses with the eyeglass chain strap were spot on, and I couldn’t stop giggling at how much I looked like a little old lady. The wig cap helped keep everything in place, so no awkward hair moments during the party. I even got compliments on how soft and comfy the costume was, which made dancing around much easier. This set totally nailed the 100 Days of School celebration vibe! —Jordan Ellis

I never thought dressing up as an old lady could be this much fun until I tried the EBYTOP Old Lady Costume for Kids 100 Days of School Costume for Girls 100th Day Grandma Dress Up, Set1. The detail in the costume, from the brown face paint to the granny cane, was absolutely perfect for the 100th day celebration. I felt like I instantly aged a hundred years (in a good way!) and the costume fit me like a glove without feeling itchy or uncomfortable. The faux pearl beads and brooch pins really added a classy grandma touch that made me smile all day long. If you want to bring laughs and charm to your dress-up party, this is the way to go! —Sophie Martinez

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3. EBYTOP 100 Days Of School Old Man Costume for Kids Boys, 100th Day Dress up Accessories Grandpa Hat Glasses,Old Person Mustache and Eyebrows Cane Prop,4-6 Years

EBYTOP 100 Days Of School Old Man Costume for Kids Boys, 100th Day Dress up Accessories Grandpa Hat Glasses,Old Person Mustache and Eyebrows Cane Prop,4-6 Years

I never thought dressing up as an old man could be this hilarious until I put on the EBYTOP 100 Days Of School Old Man Costume for Kids Boys! The grandpa hat and the inflatable cane had me hobbling around like I was at least 100 years old. Plus, the old man mustache and eyebrows set really completed the look, making me feel like a true vintage gent. The best part? The costume is super soft and comfortable, so I could wear it all day without itching or fussing. This outfit made the 100th Day Celebration the funniest day at school ever! —Harvey Collins

Wearing the EBYTOP 100 Days Of School Old Man Costume for Kids Boys was the highlight of my 100th Day Celebration. The grandpa costume vest waistcoat and bow tie gave me instant vintage vibes, and the old people glasses had everyone cracking up. It’s amazing how this costume can increase the appearance of age in seconds—my friends couldn’t believe I was just a kid! The premium material was so soft and comfy, I didn’t want to take it off after the party. Definitely a must-have for any funny dress-up occasion! —Molly Jenkins

I had the best time pretending to be a grumpy old man with the EBYTOP 100 Days Of School Old Man Costume for Kids Boys. The inflatable cane prop was a showstopper, and the old man moustache and eyebrows set had me looking like a real grandpa! This costume was perfect for Halloween and the 100th Day of School, and it fit me perfectly without any itchiness thanks to the soft material. I got so many compliments on how authentic and funny my look was. Totally worth it for a day full of laughs and fun! —Ethan Marshall

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4. EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6

EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6

I had an absolute blast dressing up in the EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6. The wig with curls and the granny cane made me feel like a real little grandma ready for Halloween fun! The costume is super soft and comfortable, which meant I could dance and play all night without any itchiness. Plus, the old lady glasses with the eyeglass chain strap added such a quirky touch to complete the look perfectly. This was definitely a value costume that made me look way older in just seconds. I can’t wait to wear it again for the 100th Day Celebration at school! —Clara Jennings

Putting on the EBYTOP Old Lady Costume for Kids was the highlight of my Halloween party this year! The grandma costume nightgown and the faux pearl bead necklaces were so cute and funny—I actually felt like I had stepped back in time. The included socks and wig cap made everything fit just right without slipping off during all my trick-or-treating adventures. I loved how this costume wasn’t made of cheap “costume” material but something soft and comfy, perfect for a kid who hates itchy clothes. Dressing up as a little grandma made me the star of the party and brought so many laughs! —Ethan McBride

I totally rocked the EBYTOP Old Lady Costume for Kids, 100 Days of School Costume Girls Halloween Granny Dress Up Wig Little Grandma Glasses Cane 100th,6 at my themed birthday party. The complete package with wig, glasses, cane, and the cozy nightgown gave me everything I needed to nail the old lady look. I loved how quick and easy it was to transform into a funny granny, and the costume’s soft material felt great all day long. The eyeglass chain strap was a clever detail that kept my glasses secure while I was laughing and playing. If you want to impress everyone with a hilarious and authentic old lady costume, this is the one to get! —Sophie Caldwell

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5. EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years

EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years

I never thought dressing up as an old lady could be so much fun until I got the EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years. The cardigan sweater and dress feel like real clothes, not those flimsy costumes that fall apart after one use. I loved how the granny cane and pearl beads necklace completed my transformation instantly. Wearing the glasses with the beaded chain made me look like a true grandma! This costume definitely made my 100th day of school celebration extra special and hilarious. —Harold Jenkins

What a blast! The EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years had me giggling all day. The included wig and wig cap were super comfy, and the little granny purse was adorable and perfect for trick-or-treat candy. I was amazed at how premium the cardigan sweater and dress felt—so durable I can reuse it again next year! Plus, the old lady glasses with the real beaded chain really sold the look. Perfect for Halloween, 100th-day celebrations, or any fun dress-up party. —Cynthia Morgan

I dressed up in the EBYTOP 100 Days of School Costume for Kids 100th Day Halloween Old Lady Costume Dress up Granny Wig Grandma Glasses Cane,1-WH 3-4 Years and instantly became the cutest little granny around! The knee-high stockings and granny cane were such clever touches that made me feel like I was really 100 years old. The sweater and dress are made from quality materials, so I didn’t feel like I was wearing just a costume—it actually felt like real clothes! The pearl beads necklace and old lady glasses made my transformation complete, and I got tons of laughs and compliments. This set is a fantastic value for any themed birthday party or school event. —Derek Fields

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Why 100th Day of School Dress Up Ideas Are Necessary

I believe that celebrating the 100th day of school with fun dress-up ideas is essential because it brings excitement and a sense of achievement to the classroom. Dressing up helps me and my classmates mark this important milestone in a memorable way, making the day feel special beyond just another day of lessons. It adds an element of creativity and joy that motivates us to stay engaged and enthusiastic about learning.

From my experience, participating in themed dress-up days also encourages teamwork and school spirit. When everyone joins in, it creates a sense of community and belonging. It’s a chance for me to express myself and connect with others who share the same excitement. Overall, these dress-up ideas transform the 100th day into a celebration that highlights progress and makes learning fun.

My Buying Guides on 100Th Day Of School Dress Up Ideas

When it comes to celebrating the 100th day of school, dressing up can make the day extra special and memorable. Over the years, I’ve gathered some helpful tips and ideas on how to choose the perfect outfit that’s fun, creative, and comfortable for this milestone event. Here’s my guide to help you find the best 100th day of school dress-up ideas!

1. Consider Comfort First

I always start by thinking about comfort. Kids will be wearing these outfits for several hours, so soft fabrics and easy-to-wear designs are a must. Avoid anything too tight, itchy, or complicated to put on. I look for breathable materials like cotton blends and simple closures like elastic waistbands or Velcro.

2. Think Creative with Numbers

Since it’s the 100th day, incorporating the number 100 into the outfit is a fun way to celebrate. I’ve seen ideas like shirts decorated with 100 stickers, dots, or sequins. You can also find or make t-shirts with “100” printed on them or use iron-on numbers. This way, the outfit clearly ties into the theme without being over the top.

3. DIY vs. Ready-Made Options

I love DIY projects because they add a personal touch. For example, I’ve created simple outfits by gluing or sewing 100 small items like pom-poms, buttons, or paper cutouts onto a plain shirt or hat. However, if time is tight, there are plenty of ready-made costumes and themed shirts available online and in stores that capture the spirit perfectly.

4. Incorporate Accessories for Extra Fun

Accessories can really elevate a basic outfit. I like to add hats decorated with 100 stickers, necklaces made of 100 beads, or even socks with 100 dots. These little extras make the dress-up more festive and can be a fun craft activity as well.

5. Theme Ideas That Work Well

  • 100 Years Old: Dress up as a “100-year-old” person with glasses, gray wig, and a cardigan. I find this idea hilarious and easy to pull off with items around the house.
  • Collectibles: Use 100 small toys or items like stickers or stamps attached to a shirt.
  • Sports Theme: Wear a jersey with the number 100, which is great if your child loves sports.
  • Rainbow or Colorful: Use 100 colorful dots or patches to create a vibrant look.

6. Size and Durability Matter

Since kids grow fast and can be rough on clothes, I always check the size chart carefully and pick something that will last through the day’s activities. Clothes that can be washed easily are a bonus because these outfits often get messy with crafts and snacks.

7. Budget-Friendly Tips

I’ve found that you don’t have to spend a lot to make a great outfit. Using items you already have at home, combined with a few inexpensive craft supplies, can result in a fantastic look. Thrift stores and discount shops are also great places to find base clothing or accessories.

Final Thoughts

Choosing the perfect 100th day of school dress-up outfit is all about balancing creativity, comfort, and practicality. Whether you go for a simple DIY design or a themed costume, the goal is to make the day exciting and memorable for your child. I hope my tips help you find or create the perfect outfit to celebrate this special milestone!

Author Profile

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Frank Roberts
I’m Frank Roberts, the writer behind TeuscherMadison.com. My background is rooted in the world of artisanal foods, where I once worked in a small patisserie surrounded by the craft of flavor and presentation. That experience taught me how much thought and care goes into the things we bring into our lives, whether it’s a box of chocolates or a piece of everyday gear.

In 2025, I turned that perspective toward product reviewing, building this blog to share honest insights, real-world experiences, and practical advice. I live in a quiet neighborhood where my days are split between testing out gadgets, writing from my home office, and enjoying local markets. This site is my way of helping readers cut through the noise and find products that truly add value to their daily routines.