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. Rachel K. says...

    I remember reading when Toby was born, and now look! He is adorable. :)

  2. Courtney says...

    I can’t even handle this post. AMAZING STYLE TOBY! I love the self-expression you can see in his outfit choices. I loved the “I wear it on the weekends” comment about the Power Ranger costume and the “I wore it on a date last night – she thought ‘cool'” :):):)

  3. Kelly says...

    haha, loved it. This kid is the best :)

  4. Kelly says...

    This is the sweetest and Toby is one cool kid!

  5. Becka says...

    Haha oh boy, this is the sweetest. Thank you for sharing!

  6. I read your blog all the time & LOVE it. I never comment on blogs but feel I have to here. Thanks for this! It’s possibly my favourite blog post of all time. Thanks too to Toby and his incredible style!! xx

  7. Erin says...

    His love for blazers is everything. Thanks for the Toby feature. It gave me a great smile this morning :) Keep rocking it, kid!!

  8. Vikki H says...

    what a handsome original! “leggings feel better than pants”, yes, they do Toby!

  9. Niharika says...

    Great post!!!! Very chic :) Perfect for this series!

  10. Lindsay says...

    Legitimately the best thing on the internet this week. Thanks, Toby! You have cool style.

  11. RC says...

    I had a long crappy day, and this was the highlight of it. What a shining light he is! 💕

  12. Christine Hart says...

    Reeeediculously cute!!

  13. jessica says...

    seriously inspired to make some blazers with leggings outfits!

  14. Michelle Chang says...

    +1 this is the best.

  15. Sally says...

    This is the best.

  16. This is fantastic! He is so right about the blazer, it is totally him!

  17. beth says...

    I love the way most of his clothes all look slightly too small– no joke! It’s so cool. I often see boys in such oversized, ugly sports crap. It’s nice to see a slim line on a little dude.

  18. Sweet Toby…

  19. VP says...

    This was fantastic!!!!! Um, “leggings feel better than pants” — wise beyond his years!!!

  20. Amanda Blair says...

    Joanna, you have the most incredible kid. He is eccentric in the best way possible. He is already such a cool person. I can’t even imagine how wonderful, loving and open he will be as an adult. Also, his romantic side just slays me. His date?! I.just.cant. Toby is my spirit animal.

  21. Adrien says...

    This is so amazing. Thank you for bringing joy to my week — go Toby go! (He is right….blazers are the best.)

  22. Jamie says...

    The most adorable week of outfits I’ve ever seen! Absolutely made my day.

  23. beth says...

    awesome!!!! :) made me smile.

  24. Diana says...

    This is the best thing ever.

  25. Nadia says...

    Yes, Toby! Leggings ARE better than pants :)
    Such a great kid!

  26. Lisa says...

    What amazing, fearless style! Toby has it all, an appreciation of a good blazer, power clashing, recognising the importance of comfort and the joy of layering. Go Toby!

  27. meegan says...

    Brilliant. What a little love! My daughter (almost 6) also dresses herself. It’s the BEST! I wish I had her style.

  28. Marta says...

    ‘I know my style — I just know” :) Love reading this!
    Toby, I love your style! – I also think layers are the best! :)
    Keep being that happy, fashionable and cute kid!

  29. ruby jo says...

    I love how he knows himself so well.

  30. Molly says...

    BEST. ONE. YET. The women you feature are beautiful and their outfits are inspiring, but this little bundle of joy is the most beautiful by far! As the momma of a little fella and another on the way, gathering clothing sources is a plus. Keep the little people fashion posts comin’!

  31. Callie says...

    He is AWESOME!!! thank you for sharing, Toby!!

  32. Amy says...

    Thanks for letting us be a part of your life and sharing your cute family with us!

  33. Helen says...

    DYING

  34. Amanda says...

    Holy crap! I long ago made the decision not to have kids, but this made the ol’ ovaries do a few flips.

  35. My favorite week of outfits so far! Makes me wish I had a little guy!

  36. MBH says...

    I feel like he’s proof that style is just born into someone–you can’t learn how to be cool. I have two sons (7 and 4) who choose their own clothes and they dress like complete disasters. Toby is AWESOME. Seriously, those last pics with the scarf? He’s much cooler than me.

    • Kitty says...

      Haha. I thought the same thing. I think my kid is awesome but stylish sartorialist she is not.

      Keep it up Toby!

  37. Anilia says...

    The. Best.

  38. My heart. Omg. We’ve been so lucky to watch Toby grow up on Cup Of Jo. This post is unbelievably sweet!

  39. Natanya says...

    Please tell Toby he is awesome and this week of outfits is my favorite. Such a great post!! Love how you celebrate his style and personality <3 So precious

  40. Molly says...

    He should watch Sing Street – he would love the changing outfits of the main character!

  41. Brandy says...

    This was awesome! Have him do another one. He cracked me up and made my morning:)

  42. Elizabeth says...

    What a gem! I laughed out loud! Toby is so fashionable and it’s wonderful that he “just knows” his style at such a young age.

  43. His blazers are so adorable!

  44. Katherine says...

    This is my favorite post ever!

  45. Nickie says...

    Officially my favorite COJ post EVER!! Beyond words!!

  46. Rebecca Sunde says...

    What a confident and self-aware young man you are raising!

    As soon as I was old enough to dress myself, my mom let me choose what I wanted to wear. I put together some pretty bold ensembles! As I get older, I’m more and more grateful that my mom let me express myself like that at such a young age. She never made me feel self-conscious about my choices, though I’m sure there were some days when she must have done a discreet double-take before we walked out the door!

  47. Janine says...

    I LOVE THIS! Particularily his 2 poses in the yellow leggings. Very modely looking. What a cool kid Toby is!

  48. Paty says...

    Oh my goodness I LOVED THIS!! haha!

  49. “Leggings feel better than pants” -Toby, -Me

    Thanks for sharing. What a great post, love his sense of style and sense of self.

  50. Fernanda Abreu says...

    I love it! Toby is a charm <3 Kisses from Brazil!

  51. Olivia Neal says...

    This is fabulous! What a cool kid.

  52. Brittany says...

    This is ridiculously cute and I need to read more of them. :D

  53. Hannah J says...

    Toby looks so fly! I love his style!

  54. So adorable!! I love his personality. So cute. Thanks for sharing!

  55. OH my gosh, Toby is so cool! I wish I had been this stylish at 6 and 3/4 (… and I’m STILL not this stylish!).

    Flora
    http://www.theeverchange.com

  56. Karinny says...

    Toby is a rockstar!

  57. Erin says...

    OMG, this is the cutest thing! Go Toby!

  58. Regan Henry says...

    I loved this! Probably one of my favorite posts of all time. Was smiling through the whole read. Thank you!

  59. Anna says...

    I feel like Toby has more style (and cooler attitude) than I do. :)

  60. Ramona says...

    I have a feeling someday he’ll be “dressing America!” ;)

  61. Ileana says...

    This is the cutest, most adorable thing I’ve seen today. Go Toby and his fashion-forward style!

  62. Rue says...

    I am dying. I am going to bookmark this in my pick-me-up/feel-good bookmark folder. I love it when little kids are independent and precocious. I should also maybe stop reading these Monday parenting posts until my relationship status is slightly more secure because these posts invariably make me want kids!

  63. Greatest thing about Toby, besides his style, is his confidence! You look fantastic, Toby!

  64. This is my favourite fashion post of all times. And not only in this blog, I mean in the history of Internet and fashion.
    Toby, you are unique and I love your style!
    Hugs,
    E.
    http://www.theslowpace.com

  65. Alli says...

    Love love love!!!

  66. jkl says...

    Love this, what great style! I had to chuckle about the car explanation. My son points them all out every day. Where I live (Switzerland) on our way to school our kids point out.. Maseratis, Jaguars, Porshes, Audis… Lamborghinis.. Ferraris….

  67. Cat says...

    Just 😍😍😍

  68. What a brilliant little chap!

  69. R says...

    This is your best Week of Outfits post, by far! Been a big fan of Toby (I still remember the sports jacket post causing me to tear up). We love you and your style, Toby. Lots of love from India.

  70. I love love love this so much!!! So sweet. My oldest son went through a stage from 3-5 where he only wore tucked-in buttondowns (and always buttoned the top button!) and khakis. Every single day all through preschool and kindergarten–and he would slick his hair down with water and comb it to the side. It was the cutest thing and I was so sad when he outgrew it and started wearing tshirts and jeans!!

  71. L.M. says...

    This is the most awesome one yet! My 6-year-old son loves gold too. He wears gold lame leggings regularly. American Apparel used to make them, but now I just get them from Amazon. Best thing ever.

  72. Lena says...

    This is the best post ever. Toby is amazing.

  73. Jeannie says...

    I ate up every word from him. SO adorably awesome!!!!!!

  74. Tracy says...

    Oh my god this was too cute! I was smiling the whole time. He is just the cutest kid! And Anton is hilarious as well. Love them!

  75. Katie says...

    What a total sweetheart and goofball. Loved this :)

  76. Kat says...

    “Leggings are better than pants.” TRUTH!

    Toby is the best. I love how much he loves color and how much he has to say about what he wears. That is a special trait in a boy, let alone such a young one.

  77. Megan says...

    So freaking cute. He’s getting so big! He looks like a real boy now and not like a toddler. Sweet Toby.

  78. Astrid says...

    Adorable! He rocks a blazer

  79. Patricia says...

    Toby is too adorable!! And he does have a great sense of style for sure! Loved seeing this post :)

  80. Ellen W says...

    As someone whose two boys wear “athletic” clothes – dry fit Under Armor shirts and baggy shorts all the time, it is fun to see a boy with a totally different style. Toby is adorable.

    • Marti says...

      I was thinking the exact same thing!! So cute!

  81. Heidi says...

    Definitely my fave Week of Outfits post. I am a big Toby and Anton fan, I always like to read about what they are doing and saying and now wearing!

  82. joyce says...

    Well, this made my week! He is absolutely THE BEST!!!!!

  83. Clari Hughes says...

    Wish Toby had his own blog! Such style and the sweetest soul

  84. this is amazing. I’ve been following your blog since before he was born, so it’s crazy to see how much he’s grown!

  85. RML says...

    Totally stylin’ cutie!

  86. Bets says...

    Best post of all time, made me smile the whole way through. I hope he never loses his string sense if self!

  87. This is my most favorite post! Thank you for this!

  88. AD says...

    LOVE THIS! I have a 6 year old boy and all he wants to wear are sweats, t-shirts and hoodies, which is pretty much what all the boys in his class wear. Toby’s creativity and sense of style is such a breath of fresh air.

  89. Toby is so adorable.

  90. Kari says...

    Toby is great! He really does have good style, and he makes good points. Leggings are better than pants!

  91. Angel says...

    I love this!

  92. Stephanie says...

    “Leggings feel better than pants.”

  93. Frankie says...

    Gold is my fav too, kiddo. And LEGGINGS FEEL BETTER THAN PANTS #preach

  94. Kellie says...

    “Gold is my favorite color”……I die!! Cutest!!!!!

  95. Milou says...

    Go Toby!!

  96. Kit says...

    The pose and the pant flare of the red costume reminds me of The Little Prince!

  97. Heidi says...

    I absolutely love this. Toby is just the cutest thing– :) And so stylish!

  98. Katie says...

    What a fun kid! This was the best!

  99. Cheryl says...

    What in tarnation??
    How do you pick from the pile of ridiculously funny things he says? Why on earth does he know his fashion stuff?
    Maybe it’s growing up in a city with so many stimulating influences? I’m always curious what makes these little people tick and why they’re so intensely drawn to certain things.
    My daughter is four and I believe she was a general or perhaps a dictator in her last life.

  100. What a total treat. Thank you, Toby!

  101. Megan says...

    Hi Joanna – I have an almost 4 year old daughter, Hannah. She is lovely, and kind, and smart, and has seriously told me 10 times in the last 2 hours that she loves me and that makes her heart feel good – she is also currently wearing a Rolling Stones logo t-shirt and blue suede booties – and so, i was thinking she and Toby could get married in about 25 years or so? I don’t think either one of them could do any better.

  102. Maren says...

    Love this so much

  103. Karin says...

    Oh my gosh! The blazer photos are amazing – and the Power Ranger on a date–adorable! You will treasure these photos I’m sure!

  104. Erica says...

    Absolutely love. Toby is my goal child.

  105. mindi says...

    Today I had a warm chocolate chip cookie (the first real sweet I’ve had since November!) and thought it was the best thing all day…then I see this. This is about the sweetest thing. And the commentary is SO 6 3/4!

  106. I’m in love. How amazing is Toby??!! He’s such an individual – if only all kids felt as good in their skin as he clearly does.

    Well done Mom and Dad… you’re clearly doing something right!!

    This post has given me goose bumps :-)

    http://www.thislifeisbelle.com

  107. Keshet says...

    So. Effin’. Adorable.

  108. As says...

    Rock on, Toby!!!!! One of my favorite posts EVER!

  109. Luv his style, and his spirit, so, so much! And the fact that he has more blazers than me!

  110. JA says...

    Priceless!

  111. Lisa says...

    This is awesome. On a rough day this made me smile Thx for sharing

  112. Maggie says...

    This is amazing!!

  113. Katie Hahn says...

    This is the greatest Monday post to date. What a sweetheart! You’ve got a keeper Jo! xoxo, Katie

  114. NK says...

    Love this kid!

  115. Joan says...

    I just literally…. died ❤ been on the fence about having a baby but throwing my pills away now

    • Tanith says...

      Haha! I was thinking the exact same thing! (And then the throwback photo of when he was just a rosy-cheeked babe with yellow pants on was the icing on the cake!)

    • Michelle says...

      This made me laugh out loud :)

    • june2 says...

      Yikes! I had to stop going to the Gap because the adorable baby clothes were rocking my logic about not having a child! I held firm in the end but cute kids clothes have nearly mystical powers of persuasion, lol

  116. Linus says...

    I’m feeling a big feeling that Toby is a dancer. A very stylish dancer.

  117. Reem says...

    This is so sweet. Definitely made my day. I like your blazer too, Toby!

  118. Jenny says...

    This is just the best! Toby is the best!! And totally agree that “leggings feel better than pants”. Stay true, young one :)

  119. Meg says...

    Best outfit post ever! You rock, Toby!

  120. Paige says...

    Oh My Gaaaaaahd

  121. Gina says...

    My son used to rock a blazer too when he was little, starting about age three. He wore it with jeans, he had longer, rocker style hair, and let’s just say more than a few ladies “swooned” and remarked, if only he was a few years older ;)
    I love that Toby knows his style already, and is so comfortable with it! He’s got great style, and it shows how confident he is in his life, I think.
    Keep on stylin’, Toby!

  122. MVP says...

    I really like the series but I love this one! Toby! Toby! (said in my best cheerleader voice).

    Can I just quote, “I wore this on a date last night” and “I know my style”. He is adorable and full of personality.

    The outfit with the scarf is perfect! Can he please teach adult, single men to dress?

  123. Leslie says...

    Outfit #5 is my favorite. Toby should have a feature in next fall’s J Crew catalogue.

  124. beth says...

    Love this! My son always had his own style from a very young age, and he’s 17 now and still stylin’. I love that Toby has the confidence to pull off a Power a rangers costume on a date (and she appreciated it!). So sweet.

    • beth says...

      Power Rangers…. not power a ranger, haha.

  125. Lisa says...

    This is amazing Joanna! It’s been so fun to watch him grow.

  126. Noelle says...

    Oh my goodness, this was the sweetest post. Toby is such a stylish little dude, and kudos to you guys for fostering his creativity with clothing! Made my day to hear his thoughts behind his week of outfits :)

  127. Amanda G says...

    Oh my gosh, this was truly the best! I have a 1 year old little guy and I can’t wait for him to just know his own style, too cute!

  128. Marianne says...

    My 7 year old has a somewhat similar style to Toby. Although he wears his blazer or vest with athletic shorts instead of leghings. He’ll even throw on a clip tie with a non collared shirt if the mood suits him. I love that he owns his style!

  129. Amy says...

    This is just what I needed on a Monday! I love it so much, and can’t stop smiling now. Haha Toby, you rock!

  130. Cazmina says...

    This is adorable.
    I love that he knows his style – I’m 30 and still trying to figure it out!

    P.S I hope he enjoyed his nutella toast!

  131. Kathy Tegtmeyer says...

    The best week of outfits EVER!!!

  132. Your son has style (and moves) :)

  133. ks says...

    I’m going on a date tonight & I’m definitely approaching it with the toby attitude – ‘HE thought, cool’ will be my mantra when I get dressed. x

  134. Lee says...

    I love that he loves leggings! My son is 3 1/2 and has been in a pajama phase for awhile, the only thing he will wear is matching pajama sets, preferably with rockets or superhero themed. If we wrestle him in pants and get him out the door before he rips them back off, the first thing he does when we get back home is take them right off! He won’t even wear sweatpants so I feel like its the tighter fit of the pajamas that he likes and it looks like Toby can relate. His style has totally inspired me for how to expand Roman’s wardrobe, Thanks Toby! :)

  135. Ellen says...

    This is the very best!

  136. Caitlin says...

    Laughed out loud! I want to have the confidence Toby has, “I know my style — I just know. ” This post makes me excited to have kids and hear the awesome things they say.

  137. Sasha says...

    Oh my god, “I’ve never had Nutella. Only once. For my birthday” at the end just killed me. On a more serious note, I did not realize how a blazer can dress up my more casual outfits for work until I was in my thirties, so kudos to Toby!

  138. Kayla says...

    “Leggings feel better than pants.” I’m dying at the sweetness of this! He is your mini twin Joanna. Thank you for sharing this!

  139. Deb says...

    This made my day. Thanks Toby!

  140. Heather says...

    Best “week of” EVER!!

  141. Carolyn says...

    “leggings feel better than pants”
    – toby

    Can i get this on a shirt?

    • Katie Hahn says...

      Ha! I’d totally wear that shirt!!

  142. Margaret says...

    Hey is clearly ready for his own blog..

    • Margaret says...

      I mean he!

    • jillygirl says...

      Right? What’s his Insta handle?

  143. I really think I could pull off outfit number five. Great brainstorming material here.

  144. Love, love, love. My little man is only 5 months old, so I’ll have to bookmark this :)

  145. Michelle says...

    LOVE! Go, Toby! My son always knew his style too and I thought that was fantastic. I still don’t know mine. :). So glad Toby shared his week with us.

  146. Most adorable post ever!!! Hello from Switzerland Toby!