Emily Henderson

Let's Play Dress Up

My 27 Favorite Pieces For A Toddler Boy’s Complete Wardrobe


When I first got pregnant with Charlie I started stalking little boys clothes and here is what I found: It ain’t awesome. Definitely not as good as the girl’s roundup we pulled together a few weeks ago on the blog. Generally what is out there is designed to have them look like miniature frat boys – and not in a fun ‘Old School-Will Ferrell’ kind of way, more like douchey-guy-that-hazes-for-no-reason kinda way. Once we had that little nugget, Brian took over shopping/dressing Charlie almost immediately. While I went for bow-ties and suspenders, he went for basically tiny versions of anything that he wore – think chinos and baseball shirts, plaids and New Balance sneakers. So while Corbett helped pull together this post, Brian deserves the real credit for how Charlie dresses. Now, Elliot? She is all mine.

Emily Henderson Toddler Boys Fashion

1. Cadet Hat | 2. Knit Beanie | 3. New York Mets Baseball Cap | 4. Stripped Button Down | 5. Cardigan | 6. Utility Button Down | 7. Denim Button Down | 8. Knit Cardigan | 9. Striped Polo | 10. Gingham Button Down | 11. Coat | 12. Quarter Sleeve Tee | 13. Corduroy Jacket | 14. Navy Polo | 15. Vest | 16. Parka | 17. Baseball Tee | 18. Red Plaid Button Down | 19. Shorts | 20. Stripped Pants | 21. Grey Jeans | 22. Khakis | 23. Plaid Shorts | 24. Dark Jeans | 25. Navy New Balance | 26. Flannel High Tops | 27. Vans Slip On

We stuck to some major basics over here – skinny chinos (#22), New Balances (#25), with a polo shirt, cardigan and a Mets or Dodgers baseball cap (Brian was a huge Mets fan but now that he’s in LA he likes both). Charlie looks impossibly adorable when we actually put these things together on him. When I shop for him I ask myself ‘Would Brian wear that?’ and if the answer is ‘no’ then I usually skip it. Every now and again I go slightly more fashion-y with him and then I get in trouble for trying too hard to play dress up with our little guy. Ultimately the keys are: 1. Stay away from logo/characters unless they are vintage inspired (we once bought a vintage-style band t-shirt for him) and 2. layering always makes kids look like mini grownups which somehow is the key to ‘old man cute’.

What are your thoughts on the boy toddler clothing game? Anything we should add or take away?

In case you missed our first girl’s clothing roundup head on over here. It is much more bright, fun, and pattern infused than the more muted and masculine boys roundup, which I still love. Now if I could only find a way to stop him from growing up so fast, where did my little baby go?

***curated by Corbett Tuck for EHD, art directed by Me.


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  1. I’d never really thought about it because I don’t have boys, but YES. Mini frat boys is the perfect description, sadly. Good job avoiding that in this round-up! So darling.

  2. When my Charlie wore something like that grey cardigan to high school, the kids called him ‘grandpa’.
    Fast forward to college, he went to a family party at a gf’s house and he and her grandpa were wearing the same sweater. hahaha

  3. I have three boys who all wear the same version of sweatpants and batman t-shirts. It’s so totally boring. They hate wearing anything with buttons, including jeans. They are constantly getting dirty, so I wouldn’t even be able to try some stylish duds. It’s a little sad for a girl who was voted, “Most Likely To Make a Fashion Statement” in high school.

  4. The most important lesson I learned when my son was small (hell, he’s 8 and this still holds true): red plaid hides all stains.

  5. finding simple, comfortable clothes for toddler boys is a full time job. why does everything have some dumb saying on the front? as a montessori family, my kids don’t wear jeans with buttons/zippers or anything else that requires an adult to be around in order to pull bottoms on/off to use the toilet. try finding cute boy pants with stretchy waistbands!

    this round up is adorable.

    1. I never thought about that but that’s a very good idea, too. We are just starting the ‘can you put on your own clothes’ movement and its not going very far … maybe the no jeans/buttons thing would help.

      1. Make sure you do jeans at least every four days so he’ll remember the feel. If you go too long, the comfort of non-jeans will overtake his brain and he’ll revolt and be 11 and still not wearing jeans. (I speak from personal experience. My own childhood and nowhistory repeating itself in my daughter. My mom calls it paybacks. )

      2. Avoid buttons. Zippers! :(
        One avoidable battle gone.
        Also, no ironing! I love many of these, but I refuse to iron more clothes, especially small ones.

    2. Gap occasionally has jeans that have a fabric band inside the waist of the jeans. My just potty trained 3 year old can pull them on and off by himself. And bonus: they stay up on our super skinny guy!

    3. My philosophy is “buy it weird, on clearance and in future sizes” to mix some craziness into the mini-dad, mini-hipster look.

      These have been great on sale:

      Also – Gap and Gymboree. Gap has fashion-forward stuff that doesn’t sell well here in MN. Example: tropical printed windbreaker purchased last year and wearing right now ($3, yes!)

      H&M is great. He has a pair of moto-skinny dropped crotch sweatpants he’s been wearing for months. I start them baggy/rolled and donate when they get snug to stretch out the wear for several months

    4. My philosophy is “buy it weird, on clearance and in future sizes” to mix some craziness into the mini-dad, mini-hipster look.

      These have been great on sale:

      Also – Gap and Gymboree. Gap has fashion-forward stuff that doesn’t sell well here in MN. Example: tropical printed windbreaker purchased last year and wearing right now ($3, yes!)

      H&M is great. Comfy, easy, fashionable and cheap… but I hate to think about where they are made.

      I start them baggy/rolled up and wear til fitted. It’s like having three looks in 1 item. Ha… yeah.

  6. I dress my little guy in mostly tea collection and zara, the styles are really cute and the cut works better on my tall skinny boy than other brands I have found. and tea has really good sales!

  7. I have two boys, ages 3 and 10. I dress them pretty much the same as your husband. The really unfortunate part is that you will be looking at the same exact clothing forever. A lot of the clothes out there for my 3 year old are the same clothes I bought my 10 year old 7 years ago. Buying children’s clothes loses its fun when you are essentially buying something you have purchased a few times before.

  8. My almost 13 year old wears flannel shirts, skinny jeans and vans. That look does not go over very well where we live. Under Armor in neon is the key ingredient. I love my guys sense of style. We live adjacent to Michigan State University, and we drive through I show my Graham that he will be the cutest college guy ever-because he dresses like one now. Tough stuff in middle school.

  9. Super cute, but my kiddo pretty much stopped letting me dress him when he started preschool at 3. Flash forward to age 10 and the only things on that round up that he “might” wear are #14 & #23 if he had to dress “nicer.” Basketball shorts, a sports-themed tee and Nike kicks are pretty much all he’s worn since 1st grade.

  10. While certainly stylish, that is the saddest toddler boy’s clothing collection I’ve ever seen curated. I’m a big fan and understand that dressing babies like adults is all the rage. But there is literally not one thing on the whole list that might allow Charlie to be enthusiastic about his clothes (other than looking exactly like dad). How about a sports team t-shirt or jersey? Or something with a truck or animal or whatever it is that he likes? There are plenty of options available that aren’t cartoon-y or over-the-top. Or even just some colors of some sort. While stylish and lovely and certainly photo-ready, albeit completely neutral, this is a sad little wardrobe to me.

    1. I totally agree. While I may not love T-shirts with firetrucks or dinosaurs, my son really liked that when he was preschool-age, and I think that’s important. Gymboree has fun stuff for little dudes, without being cartoony or over the top. Also, while the clothes shown do look cute, it’s a pain to get them on or off (too many buttons), and they don’t encourage a child to dress himself. Same with shoes with laces; there are cute velcro options out there that encourage your child to dress himself.

      1. He really doesn’t have any opinion yet, but when he does we’ll embrace it :) For now it makes Brian really happy which makes Charlie happy and that’s where the enthusiasm is coming from. I bought a ‘dragons love tacos’ shirt the other day because Charlie loves that book, but he wasn’t into the shirt. So weird.

  11. Are you a fan of any of the premium, indie brands like Mini Rodini, Bobo Choses, Wovenplay, Tiny Cottons, etc? Yes, they’re expensive, but I love the colors, personality and patterns of the clothing.

    Also, Bonds Australia has great toddler clothing. With our seasons being opposite and the conversion rate from AUD to USD, I can get 5-6 outfits for about $75 USD, even with import tax. I stock up twice a year.

    1. OOH, thats a good idea. I love those rands but I can’t justify the dough right now. But i’ll check out Bonds Australia (also since we are going there this weekend!).

  12. This represents how many people dress their little boys, that is true. For some reason little boys get dressed like miniature men. The only difference in their photos as they age is their size. My husband would love if I dressed my 2 yr old like this. I live in the South, and I know its different here, but I like babies dresses as babies. Classic clothes that were in style 150 years ago and will be 150 years in the future. My son still wears monograms and smocked outfits. I still get by with short pants and knee socks on special occasions. He has play clothes-striped pants and bulldozer shirts, too-so it’s not all dress clothes all the time. I know many find it ridiculous-but babies don’t keep. I do everything in my power to keep him looking little.

    1. I did layette too until he grew out of it! I had so much smocked baby stuff. Love it. I still do vests and bow ties and and short pants with a newsboy cap for special occasions, as well. Janie and Jack always has lots of sweet options if I don’t feel like ordering from a boutique, and in the north that’s harder to come by.

    2. My little guy looks equally adorable in “old man” clothes (cardigans and bowties), preppy stuff (chinos and button downs with the sleeves rolled up), and classic Southern smocking. He is rocking a monogrammed jon jon with white knee socks and saddle shoes come Easter morning. I know my time is limited in dressing him in that stuff so I make as much of it as I can….but I also think he looks super cute in the other styles. I’ve honestly had so much fun dressing a little boy – I love his clothes!

  13. Wow, I don’t remember fashion for boys being a thing when I raised mine. And this was in California too, not in some outpost. I don’t like logos and cartoons so basically I filled their drawers with solid color sweatpants, sweatshorts, tees and turtlenecks, and let them pick out their own color combos. All from Gap and super easy to restock. No, they didn’t dress like Dad, but that wasn’t the goal. Ease in self-dressing, comfort, and free movement in active play was my aim. I always kept one nice outfit, say navy chinos and a brand new (non-stained) striped t-neck and belt at the ready for the occasional dinner out or fancy occasion. I don’t think they owned a pair of jeans until high school.

  14. I love all these pieces, but I would pair them with some brights. My 6-year-old son loves nature and bright colors (especially orange) so I enjoy picking out his clothes to fit those interests. He also has a thing for glow-in-the dark shirts so that adds a little fun to the mix. Mini Boden, Gap Kids, and Crewcuts (ahem-only with sale prices) are some of my favorites for ‘nice’ clothes and Old Navy and H&M for the basics.

  15. Thank you for posting! My group of girlfriends is tired of me raging about how awful/gender specific/low quality boys clothing is: one more “chick magnet” tee for a 2 year old and I might lose my mind.

    I do have REALLY good luck with H&M for boys clothes. Cool joggers (an awesome jeans alternative), fun colors, more funky prints. And actually, they cut their clothes longer so sleeves and shirts work well for my tall toddler.

    1. Haha. Or the Valentine’s Day “heart breaker” shirts. Why do we want our boys to be, dare I say, douches? I want them to be nice, and not a frat boy chick magnet. I love h & m too.

  16. I have a 21 month old boy and I would be a terrible mom if I only dressed him in jeans/khakis and button downs. Maybe he’s different than other boys, but my little man likes to run, roll, flip, and play and I have to accommodate that. He does have cute jeans, button downs, cardigans, etc for church or special occasions but for every day, not so much. Never will I ever do a graphic tee with cartoons or words on them (unless he’s wearing something my mother in law got him while at her house). I do cute almost harem pants from old navy for play because I don’t care about him ruining them, and NANO cotton pants for play dates, Gymboree, or when we’re seeing other people. The pants are so nice and elevate comfy clothes for tots. Shirts are always good quality cotton that wash well- Boden, Nordstrom, NANO, and plain tees from carters that can be ruined. Cute, comfy, clothes for my little man is my mission!

  17. I suppose it’s because you live in rain-starved California, but it makes me sad not to see a cute pair of rain boots in the mix. Puddle stomping is my 2-year-old boy’s favorite pastime. I love Mini Boden and Crewcuts for splurges (only buy on sale still); cute, comfy legging-style pants from Zara kids; H&M and Old Navy for t-shirts; and the greatest find of all… JC Penney! Their Okie Dokie t-shirts hold up better than any other brand. We have a little girl on the way any day now, and I have to admit I’m psyched to dress her!

  18. I let other moms do the curating for me. We are in the suburbs of Chicago and they have awesome used kids clothing sales twice yearly all over the area. We live in a great school district next to a wealthy school district. I volunteer at their clothing sales so as to have first pick of the barely worn clothing that is consigned/donated. They do quality control so nothing is worn out or stained. I pay $1 – $5 for really nice, barely worn, jeans, pjs, tees, button down shirts and jackets. I just picked up a black Calvin Klein three piece suit with a Nordstrom dress shirt for $8.00 for my son.

    It’s encouraged me to be a much more relaxed mom – “sure, go play in the mud” because I’m thinking, “I only paid $4.00 for your whole outfit and if you ruin it having fun I’m okay with that” rather than, “are you kidding me? I paid $20 for those jeans! Get out of that puddle!”

  19. Agree, agree, agree. We have 2 boys; 7 and 1.5 (with bay girl due in August! Yay pigtails and polka dots! ((why aren’t polka dots an acceptable print for boys mainstream fashion lords?!)). My rules for dressing boys is remarkably close to yours. I will say, I love to interject bright solid colors in there, which can be hard to do. Enter crewcuts girls department! They have supplied dozens of bright, fun, unexpected pieces to my kids wardrobes of the years. AND kuddos for them not making everything so gender specific.

  20. Love this…and my “little boys” are now 22, 20, and 19. I laugh (so hard!) at my younger self that carted these boys to neighborhood outdoor parties with matching Gap jeans, button down shirts, vest, and hiking boots. I thought it was so cute – my triplets. My friends must have thought I was nuts. On a MUCH more important topic – has anyone pointed out how much you look like the “now famous for 10 minutes” Lauren B??? I saw you in the audience at the “Women Tell All” – how fun! Love all you do Emily and have been a fan since watching you win Design Star!

  21. Enjoy this stage while you can! I have two boys, six and four. I used to put all these cute clothes on them. Then, they turned three and a half and completely fought jeans, sweaters and button down shirts. It is a fight not worth having, so it is Star Wars tee shirts and Nike gym pants every day. I miss those days!

  22. So is layering and “old man cute” good or bad? I couldn’t really tell from the way you phrased it. I’d assume a toddler wouldn’t want to wear layers of clothing, but since I don’t have one I’m just going with my gut.

  23. I have a 6 year old boy and 15 month old girl. While I certainly like going for things that are similar to what I wear or mini versions of adult clothes, I try to keep in mind that my kid is into superheroes and sports and cartoons. When he sees a crazy t-shirt with a zombie on it and loves it, even though it’s not “IG/blogger chic” I get it for him because he’s six.

    I didn’t go through the pieces’ links in this post, but I have to say there is another very popular blogger with a similar readership who posts about her girls’ outfits and they typically cost about $130+ for an outfit for an 18mo old. It drives me nuts.

  24. Each of these pieces is adorable – mini puffer vest! indigo denim! – but I really yearn for color. I’m a new mom to a baby boy and have been stunned to find what passes as “unisex” and “boy.” Often like watching an old black and white film. I’m definitely over the categories, period. Why shouldn’t boys wear bright color and pattern? I plan on dressing my son in ALL colors – pink included. Kids have their entire lives to decide what denotes masculine and feminine and it feels like they’re shoved into such limited concepts of gender from the get-go when it comes to clothing. I love your blog and read it regularly…would love to see more of a challenge to the status quo. : )

    1. Congratulations! I love hanna Andersen and polarn o. Pyret for bright colors and unisex clothing. They are both durable and happy, so that’s what my little 15 mo old boy wears until he decides. :)

  25. Very nice! What blows though is no matter how cool some of those shoes look, they are a total stink to put on wriggly, fat heeled toddler feet! But girls – well they get the nice mary janes and those are easy to put on. Love the look of slip ons – hate trying to slip them on. Maybe there’s a trick?

  26. Having three boys, this is my number one complaint aside from potty training (trust me, it ain’t pretty). Girls get box pleats, ruffled sleeves, embroidery, fresh color combos. Boys get a dino, truck or super hero slapped on a tee and they call it fashion. Boys get messy. They care more about comfort than a special detail BUT even target is carrying affordable cute girls clothes. I agree on the no buttons, snaps and skinny jean thing. That isn’t saying much though bc my boys would live in their underwear and a snuggie blanket wrapped around them if I let them.

  27. I have never in my life seen a toddler dressed in clothes like you show in your round-up! Buttoned down shirts? Jeans? Cardigans? I guess you do things differently in LA! Toddlers around these parts wear sweat pants, printed t-shirts or sweat shirts and usually more than two outfits a day because of spills, and other dirty stains accumulated as the day goes by!

  28. I have 4 boys (1-6 yrs old), so I say good luck keeping them away from the logo shirts!! It’s so sad that I’ll buy cute polos/shirts and they will always go for Ninja Turtles or some superhero….well, except one of them. He likes suspenders and fluorescents. Like I said, Good Luck!

  29. Thanks for this! We’re adopting a toddler from Korea later this year, and he’ll be 2 1/2 when we bring him home, so we’re going to have to do this whole entire wardrobe thing at once. I’m considering this my starter kit. There’s little info out there on how to register (and generally plan) for air-dropping a toddler into your life, so this is another little piece of my puzzle solved.

  30. LOVE the slip on vans….I keep just buying the next size up in these for my son since they are so easy to slip on but hard for him to take them off! I find the real struggle in dressing my boy is avoiding all the “cutesy” stuff with ridiculous annoying sayings on them like “heartbreaker” or “ladies man” etc. I always have good luck at Zara for kids and a shop I discovered recently called FOX + FOUND http://www.shopfoxandfound.com They have more hipster baby boy clothing like harem pants and beanies etc but it’s decently priced and comparable to Zara or Baby Gap just more unique.