Fashion Friday: Henry Gates, Fashion Plate

To say I have fun dressing Henry is the understatement of the year. Picking out the day’s outfit brings me a generous amount of glee every morning! (He, however, is less thrilled- as of late getting him dressed is like trying to put a duvet cover on a fast moving comforter (a great quote from Jim Gaffigan- if you have not read his book “Dad Is Fat” you need to- I cried laughing).

And to say I have fun SHOPPING for Henry is the second understatement of the year.  When he finally started fitting into Crewcuts I nearly cried with joy.  I thought shopping for boys would be so boring compared to girls, but the options are so adorable now for little dudes (other than all the clothing with weird slogans like “Space Hunk” and “Mommy’s Boyfriend” — uh, NO).  I know in a few short years (months?) he’ll start having opinions about his attire, but until then I plan to dressing him how I want- which some days is Stockbroker On Nantucket Baby, others Hipster Brooklyn Baby and others still  Classic Country Rockwell Painting Baby. A lot of you ask me what Henry is wearing on Instagram so I wanted to do a post about what he wears- I shop a lot at H&M (best organic onesies out there- don’t bother with any others), Zara, Boden (20% off today), Joules, Gap Kids (40% off today), Crewcuts (30% off today), Carters, Oshkosh, Old Navy, Nordstrom, Tea Collection (20% off today) , Lands End, Target (Cat & Jack line is so cute), Gymboree….so, basically everywhere?

Today we went more Weekend Prepster….. (captured trying to put Ollie’s harness on the stone dog- die.)

shirt (similar) // jeans // shoes

I have a REAL addiction to buying him shoes. THEY ARE SO TINY I CANNOT HELP MYSELF.

This was us walking in the rain the other day- plaid shirt and denim sweatpants are last season (the horror!) from Splendid, which makes such soft, high quality stuff.  I know you can’t see past the tiny baby slicker though, which is all that matters. And that FACE (he was watching a bird).

Raincoat // sneakers

Serious Henry guarding the stairs after I merely mentioned thinking about changing the runner. He (and you) all said no so…. I’m not gonna mess with him.

shirt // pants // shoes

This kid is heaven- I want to eat him up. He’s the happiest baby on any block and just LOVES being outside now that the weather is warm.  Even when I dress him like this.

sweatshirt // pants are no longer available, but similar here // sneakers

Here are a bunch of outfits Henry wither already owns or has coming (because doing this post was really quite violent on my wallet).

1. // 2. // 3. // 4. // 5. // 6. // 7. (also super soft) // 8.

1. // 2. // 3. // 4. // 5. // 6. // 7. // 8.

1. // 2. // 3. // 4. // 5. // 6. // 7. (also these are great) // 8.

And while shopping for the little man, I also picked up a few things for myself this week such as this bronzer  (light, matte and smells like Coppertone+sunshine+a pina colada – I basically huff it), this shirt I LOVE- long, lean and on SALE (size down), these slip on sneakers and these lightweight weekender pants.

Have a great weekend you guys!


  1. You dress Henry so well- I have the toughest time finding cute boy clothes. It seems like everything is either burnt orange or has “daddy’s little slugger” on the front! Thanks for these finds!

    Xo, Brittany
    Weekend links + steals on my blog today!

  2. Il est à croquer! I want to gobble him up!
    I really miss those days. And the years just after–big enough for an opinion, which in my daughter’s case was insisting that skirts twirled adequately. Simple pleasures.

  3. Yes, enjoy every second of dressing him and don’t feel bad. They are only babies once! And really one day out of nowhere, they will have an opinion and only want to wear the most random stuff. It happened earlier than expected with my 2 year old boy, and the only way I could get him into his precious button-on for Easter this year was with the help of Sour Patch Kids.

    1. Could go either way…. I still pick out my 9 year old son’s clothes (though he often insists on putting a Patriots jersey over everything), and I could easily see him letting me continue to do so for the next 6+ years. He’s sporty, but lazy :)

  4. I’ve been having a lot of fun dressing my 16-month old boy too. It’s a little challenging compared to a girl (or so I imagine) but there is decent stuff out there. Just gotta wade through so much mottled grey and ridiculous slogans and characters. My guy’s look is “bohemian prepster” and I too am obsessed with tiny shoes (little leather ones particularly).

  5. 2 girls and DONE, but super cute outfits make me think about a boy for about one second before I am returned to my senses! Did order the green pants for myself though – perfect summer bumming around option

  6. That last photo of him made me laugh out loud. It’s almost like he’s saying “Are you serious with these pants, Ma??!!”
    He’s such a cutie!

  7. you might also like Sabah’s for little kids -the smallest size they carry are in a size 8. You could get matching ones for dad. My husband loves his – sort of funkier take on a boat shoe.

  8. The best thing about dressing your son well from day one is they learn from your example! He will never want to wear track suit bottoms as real pants. You are shaping his taste!

    I firmly believe that dressing well is a form of good manners (thank you, Tom Ford) and teaching this to your kids is as important and useful as “please” and “thank you”. This is another form of great parenting and he will thank you for it later.

  9. Yes! I love dressing my 20 month old son, too. We shop at the same places. Definitely recommend Jcrew Factory’s crewcuts section, too!

  10. Honestly, as a mom of a little one myself in my opinion, you put him in pretty uncomfortable clothing. Too many tight jeans – it would be so great to let him relax in some more comfy play-time clothing!

    1. I love everything Henry wears and it seems none of it has slowed him down. Pretty comfortable I would say! Henry is a class act!

    2. Nothing here looks tight. Henry looks adorable and perfectly comfortable in every picture. Thanks Erin for sharing your sources. I remember how hard it was to source well-made clothes for my three boys when they were small.

  11. I have a 2 year old maniac, and I love these Henry posts! I dress mine like a little man some days…or we have some “nice” sweatpant outfits (ha!) if we’re staying in or going to gymnastics. We love all the places you listed… but have you tried Rockets of Awesome??? It’s been a game changer for me because they have such great basics. They start at size 2; it’s like stitchfix for kids. Love love love (but my wallet hates lol) (That link gets you a free item!)

  12. So adorable! I loved dressing mine when he was that age. Enjoy while you can. Way too soon all they want to wear are athletic clothes. Ugh. I go shopping at Dick’s Sporting Goods. Depressing.

    1. This. If it isn’t shorts or sweatpants my 8yo won’t wear them. .. ant this if after years of dressing him up like Henry! Hope you are better at keeping the cute look going than I was. I have to beg him to wear jeans!

    2. Ha! Same here in elementary school. Saving grace for middle and high school is school with collared shirt dress code, although the boys all top their nice Vineyard Vines button downs and polos with hoody sweatshirts…ugh!

  13. O.M.G. He is so freaking cute! But I sincerely hope you have another baby so that you can have a child that looks like you because Henry is ALL Andrew!!! Like, he’s a tiny clone and when you dress him like that, even more so!

    P.S. Don’t change out the runner. I will come to you from Canada and cry on your doorstep!

  14. I adore everything you create and Henry is no exception. A very handsome young man. My question for you is where on earth did you get the black striped fabric that is on the chair on the cover of your book? Is it one fabric or two, a black and white sewn together? I want to re-do a pair of living room chairs in the same. Thank so much.


  15. Love all henry’s outfits. Could you recommend a pair of dress shoes for a boy toddler ( like Henry). Everything I find in his size is casual or looks like a cheap pimp!!! HELP!

  16. Henry is precious! I like that he’s guarding that runner! It is truly one of my favs… you mind me asking who the maker is? Thanks Erin!

  17. So cute!!! Enjoy! Before you know it he will only want to wear athletic shorts and t-shirts.

  18. THANK YOU!! Please keep these post coming! I love getting inspiration for how to dress my little guy.

  19. He’s so cute! This reminds me of how I used to dress my boys. Oh how I miss those days. Now I look forward to any day they have to dress up. I get a music concert and first communion this week…yay! Nantucket reds are patiently waiting.

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