// Dressing Little Boys (+Toby's Outfit of the Day!)

I'd be lying if I said I didn't have a storage box full of dainty little vintage dresses for a future daughter. Ever since I was younger I envisioned what it would be like to have a little girl of my own. I think it has a lot to do with idealizing my relationship with my mom since it was just me and her growing up. She instilled a lot of really important things in me over the years and I've always hoped to pass that on to a daughter at some point. Plus shopping with your daughter just sounds fun, right? I would "ooh" and "ahh" over dresses and tutus when I went shopping, but never really paid much mind to what was available for little boys. I'm 110% stoked to be the mom of two little dudes (!!!), don't get me wrong. But before Toby came along, I was oblivious to the style choices out there for fellas. Most little boys sections in the store are covered in Superman and Cars tees, and while there's absolutely nothing wrong with that, it just never made me excited about dressing a kid. 

When we first got custody of Toby, we seriously had to start from the ground up. He came with the (inappropriately sized, very worn) shirt on his back and that was about it. Since we had all of about 2 days notice that we'd be bringing him home, we were not even remotely prepared. We knew we wanted to give him a wardrobe that could function both as play and dress clothes, but we weren't in any position to shell out mad cash for it. We started small and over the past 2.5 years we've built a nice little collection of items that he's excited to wear. (Of course in the past month he has had a growth spurt and totally outgrown almost everything, but I guess that's to be expected! haha We had to cut several pairs of his skinny jeans into cuffed shorts just this week!) 
I think it must be because of how Mike has dressed the past few years, but Toby doesn't blink twice at most graphic tees or character clothes. When he sees something in the store that he wants it's almost always an oxford button-up or a polo of some kind. He really tries to emulate Mike's style and it's one of the most precious things in the world. (See this photo for a recent example!) Because of his affinity for Dad's aesthetic, I've found myself falling in love with little boys' clothing. The boat shoes! The cuffed jeans! The bow ties! (Seriously, the bow ties! Toby begs to wear one to school every day and his teachers just die over them haha)

As shallow and materialistic as it sounds, I love shopping for Toby because I love that he loves clothes. It's something that we get to do and enjoy together. He dresses himself each morning and my heart melts into a puddle when he asks for help buttoning the top collar for his bow ties. Being able to watch his style progress through the years has totally done away with my "outfit envy" in the department stores. While I would love to have a daughter one day down the road, I love that I get to wake up each morning and witness such a stylish young man pick out his daily outfit. Toby loves clothes as much as any girl ever would so I'm not missing out on anything at all. When we go to photograph my outfits for the blog, he always politely asks if we'll snap some photos of his outfit, too. (I should really share more of those sometime... He's a total ham for the camera!) The part that really gets me? When he says that he's going to teach his baby brother how to wear bow ties! (Y'all! Come on! Just thinking about that makes me tear up.)
Of course as much as I love the oxfords and boat shoes and whatever else, we have to be very mindful of how much we spend on these items. Have you ever been around a 5 year old?! Most of his tees don't last a week and his shoes are black and scuffed after the first jaunt on the playground (Don't even ask how much playground mulch we've accumulated in our house thanks to what he brings home in his shoes...) Such is the destruction of a little boy! Haha 90% of Toby's wardrobe has come from Old Navy over the past 2 years because it's practical, functional, and affordable (The Back to School sales are unreal!) When he comes home from school with a pesky dirt or juice stain that won't budge, the shirt gets washed and tossed into a "play clothes" drawer and then that's what he wears to roll around in the grass outside. It's a constant and steady rotation of "school-to-play" in our house. 

I'm excited to see how Toby's style progresses over the years. Part of me wonders if he'll always be the button-up wearin' kind of boy, or if he'll fall more in line with what the rest of his friends normally wear. I think a lot of people are sometimes surprised to hear that Toby dresses himself in bow ties and boat shoes rather than us forcing them on him, but we said from the very beginning that it was important to us to let him determine his own style and identity. Of course I'm totally stoked that he likes what he likes (for now at least), but I'm also excited that I'll get to pick Baby Flynn's clothes at least for a few years haha!

And just a heads up for those of you mamas and papas out there, Old Navy is kicking off a Kids & Baby Sale this weekend, May 10th, at their flagship store in NYC. There will be a boatload of goodies for $10 and under, and the theme is a Kids Carnival! Obviously Nashville is a bit far for us to be in attendance, but hopefully some of y'all can swing by and take part in the festivities. There will be face-painting, carnival games, etc. A fun time for everyone! If you're like me and can't make it for the carnival party, you can still take advantage of some major steals online this weekend. Seeing as Toby's clothes are all about 2 inches too short, I'll be stalking the site for sure.

Toby's outfit: Old Navy oxford, skinny jeans and sneakers. Handmade (by Mike!) bowtie

This post was in partnership with Old Navy. All opinions and words are my own. All the items in the above collage can be purchased at OldNavy.com! (Many of them are currently on sale, too!) Thanks for allowing me to share select sponsored content on TCGG.


  1. This is too cute! Very cool that he picked up so much from Mike's style. You have the cutest little fam.

  2. Most people think I'm lying when I say I'd like a house full of boys! I kind of hate the expectation is that a baby girl is automatic excitement and a baby boy is an idea to get used to. Not sure if you experienced that reaction at all, but its definitely something I've witnessed! Boys are so much fun and I love their clothes. I'm sure it takes a little more effort to find stylish young boy clothes but thanks for proving its not only possible but that Toby enjoys wearing them!

    Rachel Kathryn

  3. He is one stylish dude! I totally get what you mean but luckily even though I don't have my own children Ive experience that boys can be as much fun to shop for and dress through my nephew.

  4. ahww........you're such great parents !! Not just Toby's cool style (and bow ties) but you can see how happy he is by the smile ox

  5. I love dressing boys! We always find the raddest clothes at h&m for a super reasonable price, and also I hit up Zara kids when they have sales. and I think it's adorable that Toby wants to be just like his dad, sweetest thing ever.

  6. This post made me smile so much, Toby is such a cute little dude! That's awesome that he loves fashion and to dress like his dad. He has such great style!

    Lauren // Lipstick & Lacquer

  7. Your little man makes my heart melt! I hope my future children as as fashionable as yours is! xx

  8. Oh he is just so cute, I love little boys wearing bow ties. I'm little ones just a year not really up for wearing bow ties yet but I can't wait xo

  9. My friend Jo and Scott have a little boy who will be four soonish and he always wears a dapper little English cap, and they get asked all the time if they make him wear it - and no, it's because Scott wears hats like that and Ben begged to get his own to look like Daddy. He often shows up to things looking like a dapper gentleman because he wants to look like his dad. I think it's awesome to see!


HEY! Thanks for dropping by. xo KB