I have about as much fun dressing Henry as I did as a little kid with my Barbies.  While boy clothes certainly are not as varied in styling options as little girls (I can’t enter Janie & Jack without a serious case of wombfire from the miniature leopard coats and gingham skirts).  Even so, it’s a freaking blast to shop for him. And while Henry is 90% of the time solidly a preppy-nautical dresser, I do like to mix it up with a little camo now and again too. :)

A lot of you asked for a post about what he’s wearing, so here’s a round up of current favorites, MANY of which we already own, in the various styles of Henry….

These jeans (PREPPY #2) are my most favorite of ALL jeans for Henry, and not expensive. And how about those Liberty swim trunks with dinosaurs??? HELLLLLOOOOO.  Also a big fan of investing a good Vineyard Vines fleece (PREPPY #10) or sweatshirt once a year (pricey but so well made) as I throw it on top of almost everything when it gets chilly.  For footwear we adore the Sambas (HIPSTER #5)  and Converse (HIPSTER #6) and they add a smidge of a cool touch to any of these outfits.

PREPPY HENRY: 1. // 2. // 3. // 4. // 5. // 6. // 7. // 8. // 9. // 10. // 11.

HIPSTER HENRY:  1. // 2. // 3. // 4. // 5. // 6. // 7. // 8. // 9.

Stripes and stripes and MORE STRIPES! :)  Henry wears these Crocs loafer rubber shoes a lot in the summer (NAUTICAL # 7) and while I try my darndest to avoid buying heinous Paw Patrol or other cartoon shirts, he IS a kid with fierce passions for trucks and animals, so I love this striped excavator shirt (PLAY # and cute safari tee (PLAY #9). Everyone wins. Also we are OBSESSED with Plae shoes- he has these (PLAY #3) and they are amazing!!!

NAUTICAL HENRY:  1. // 2. // 3. // 4. // 5. // 6. // 7. // 8. // 9. // 10.

PLAYGROUND HENRY: 1. // 2. // 3. // 4. // 5. // 6. // 7. // 8. // 9.

Have a great holiday weekend guys, I’ll post Monday but then taking the rest of the week off from blogging until Friday!


  1. omg this is soo cute! i have a 2.5 yo boy also, can’t wait to order some new stuff for him! RIP my checking account

  2. He is so adorable. He radiates sweetness! Have fun styling him because it wont be long until he want to pick out his own things.

  3. These are great! My husband’s name is Henry and I jokingly call him Hipster Henry! Has such a nice ring to it ;)

    Love this roundup – “Henry” has great style!

  4. The 2nd picture, Henry in a sports jacket, is the cutest thing I’ve seen in a long time.

  5. We bought my 22 year old son that exact K-Way jacket (Hipster #7) when we were in Italy last year. He loves it and I have wished that I had bought one for myself! Glad to see JCrew carrying them. Here’s hoping that they add adult sizing.

  6. Love this- I have two girls and still was disappointed to not have a 3rd girl since I wasn’t done with frilly dresses and buckle shoes. It’s nice to find some sources for good boy clothes. I am interested in knowing where you found the quilted brown jacket Henry is wearing in the photo? My little guy had one that was a gift and he LOVED it but it was a British brand and now I can’t find a replacement.

  7. Henry is so adorable! Thanks for this post.. i loved it & bought a bunch of new things for my little guy :)

  8. I’ve got an almost 3 year old, and he owns a lot of this stuff! If you are on the lookout for some well-designed “cartoon” shirts, hit up Old Navy. We just got some really fun ones ;)

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