Motherhood

A Week of Outfits: Toby

A Week of Outfits: Toby

For his entire life (6 3/4 years and counting), Toby has been a fashion maven. He loves mixing prints — “I know my style, Mama,” he often tells me — and he even asked for a sports jacket for his fourth birthday. So, when Toby overheard that we did a series called “Week of Outfits” on the site, he begged to do one of his own. Without further ado, here are five ensembles that Toby wore in a week…

A Week of Outfits: Toby

T-shirt: Winter Water Factory. Button-down: American Apparel, similar. Blazer: J. Crew. Leggings: Polarn O. Pyret.

“We got these pants because we forgot pants at my swimming class. I like these leggings; they have leaves from a tree. It’s cool to wear different patterns. I have a new haircut. I got Simon as a haircut present. I’ve been practicing.”

A Week of Outfits: Toby

Sweatshirt: Young One Apparel. Blazer: J. Crew. Pants: Rockets of Awesome. Backpack: State Bags.

“I like blazers because it’s like a grownup. I like wearing layers. I know my style — I just know. Sometimes I pick out clothes for Anton ’cause it’s nice. I picked out his shirt this morning.”

A Week of Outfits: Toby

A Week of Outfits: Toby

Power Rangers costume: Disguise.

“This costume is Tyler, the red Dino Charge Power Ranger. I wore this on Halloween, and I wear it on weekends. I’m not allowed to wear it to school, only when it’s Costume Day or something. I wore it on a date last night. She thought, cool.”

A Week of Outfits: Toby

A Week of Outfits: Toby

Shirt: Winter Water Factory. Leggings: Mabo.

“I like the cars on this shirt. Cars are awesome because they are cool. I know Volkswagen, Nissan, Toyota, Jeep, Hundai, Honda, Chrysler, Ford and GMC. I wore these kinds of pants since I was a baby.”

A Week of Outfits: Toby

A Week of Outfits: Toby

T-shirt: Winter Water Factory. Blazer: Kitestrings. Leggings: American Apparel. Scarf: Knit by great-grandmother.

“I like this blazer because it looks awesome. The buttons are gold, and gold is my favorite color. I wore the blazer in Aunt Lesley’s wedding. Leggings feel better than pants. We’re having Nutella toast for breakfast this morning. I’ve never had Nutella. Only once. For my birthday.”

Thank you so much, Tobes!!!! I love you!

P.S. Our real week of outfits series, and Toby and Anton in conversation.

  1. Alice Wood says...

    Argh he is so cute! I can’t wait to see my daughters style emerge! I very much second (and third and fourth) the idea of making kids week of outfits a regular thing! X

  2. Pam says...

    I need Toby as my stylist!

  3. Deidre says...

    I just came across this and wow. I could not love little Toby more! Thank you for this. It just made my day.

  4. “leggings feel better than pants”
    Right on, Toby! That was amazing. I would love more kid outfit posts! Maybe collaborate with humansofny…

  5. Leah says...

    More fashion posts with Toby please!!!

  6. Laureg says...

    I realize I’m really late to the party, but DANG, the whole post is so freaking adorable and awesome! Good for Toby, knowing his style! I especially love the dapper jackets, he’s such a gent and a true original.

  7. Veronica says...

    “I wore it on a date last night. She thought, cool.” AMAZING! I will follow his fashion Instagram when it comes out. Or whatever Instagram is in the future…

  8. Tess says...

    “She thought, cool.” Heehee, such a cutie!

  9. Amie says...

    GAH! My heart explodes.

  10. I think I just died from cuteness! Toby knows his style and he’s great at it ! As he gets older , it will become even more defined. I think he grabs ideas from the environment and people around him. Ah reminds me of my nephews and nieces who grew up and their style just evolved! As I say to my niece , you went from glitter tutus everyday to glitter skinny jeans. Your style defines you. Build it now and embrace and add forever. Did I mention that one nephew has gold Nikes! I’m the influence that rubbed off on them lol

  11. Anna says...

    This is so funny! – He has wonderful style!!!

  12. Nicole H. says...

    This is actually THE cutest post of all time! I am dying. So cute. Thanks for sharing. Toby is the coolest!!

  13. Kathy says...

    My favorite post so far! Toby needs to be a regular. He a natural and so insightful. I loved this!

  14. Jessica says...

    Dying! Joanna he is a dear. I only hope my two little boys grow up to have their own sense of style just like Toby does.

  15. Jennie H. says...

    Toby has incredible style – this is one of my favorite posts you’ve ever done. Kudos to Toby!

  16. Ellen says...

    Oh my gosh can we make kids’ Week of Outfits posts a thing? This is amazing! Way to go Toby!

  17. He rocks!! I think I need to stock some blazers for boys in my shop! Did not know how cool they can look. Thank you Toby!

  18. vivalask says...

    This. Is. Amazing.

  19. Sarah says...

    This is one of my favorite Cup of Jo post to date. Thanks for sharing! And thanks for being awesome, Toby.

  20. Nailed. It. Rock, on, Toby!

  21. Aggie says...

    This just made my day. He is SO cute, and reminds me a ton of my son. He even has the same winter water factory cars tee and mabo pants!!!!

  22. Jess says...

    OMG, I thought he was giving the finger in the second to last picture, which is the only thing that might have made this post even better! ;-) Also “I like this blazer because it looks awesome. ” I feel you, little man! Keep on doing you.

  23. jessie says...

    this is literally the cutest thing on the internet right now. i think my ovaries exploded at “gold is my favorite color”. what a rad kid!

  24. Patty Smith aka Grammy says...

    I have been following you since Toby was a baby. He was and is such a beautiful child, as is his brother. I just so enjoyed seeing this. He has great style and a wonderful sense of humor. And you have been able to give him resources for such cute things. I have loved watching Toby. He is a little younger than my grandchildren. Good for you for helping him express himself with such personality! I look forward to many more years of Toby and Simon.

  25. Theresa says...

    What a kid! Love it! He has awesome style!

  26. Ohnomyboots says...

    Yup, best CoJ post EVAH.

  27. **all the heart eyes emojis**

  28. Caitlin Noelle says...

    this is just the BEST. been reading since this guy was a little baby and my socks are knocked off. what an awesome person. and i have to say, i share his opinion on leggings, but he def got there before me. thanks jo and family!

  29. Claudia says...

    My heart just exploded! This kid ❤

  30. Amber J says...

    This is the best. Toby dresses better than I could ever hope to. More of these, please! <3

  31. Kira says...

    Well done, Joanna and Toby! I love that he has so much personality for someone who’s not even 7 years old. Keep up the great work!

  32. “Leggings feel better than pants.” Truer words never spoken.

  33. Lauren says...

    His attitude!!! so precious!

  34. Awe, what a guy! Toby has the smiliest eyes :)