I can’t believe my big boy is off to 3rd grade! I’m actually very excited for him — he’s going to a new school and was lucky enough to be placed in a class with a great group of kids, some of whom are his closest buddies! (Don’t worry, he’s been warned that there better not be any fooling around!) September is usually still warm in New York, and since school starts even earlier this year, back-to-school still feels like summer. So as much as I would have loved to dress Matteo in a cool fall outfit, it just wasn’t ideal on a 90 degree day. I decided to send him in a tank top, shorts and sneakers — basically as comfortable as possible. Despite this, I did do some fall shopping, and earlier this week we held a fun back-to-school shoot featuring our favorite brands!

For the shoot, we went to one of our favorite nearby parks — Old Westbury Gardens. The whole process was a collaborative effort between Matteo and I — from shopping to shooting, I always allow him to make choices.

At the park, we found this giant log that looked like a pencil and Matteo became obsessed with it, carrying it around and begging to take it home. While we eventually convinced him to leave the log behind, it did make for some cool photos!

I really love this look; it’s preppy and stylish. You can really play around with all of these pieces, making dressing time very easy! The socks have lobsters on them; they’re too much fun! The polo, shorts, socks and sneakers are all from J.Crew. While I do love specialty boutique brands, I feel like you can never go wrong with Crewcuts! The jacket and bracelets are from Scotch & Soda, another one of our favorite brands!

We hope all the kiddos have a great school year ahead!

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