After the extreme adorableness of Mazzy and Gavin’s first date on Valentine’s Day, a clothing line called Janie and Jack asked if I’d like to feature their latest collection in another date, only this time swapping out the models for Harlow and Gavin’s little brother Luke. They explained that their toddler collection has a preppy East Coast vibe inspired by imagery from Montauk.

Hmmmmm….. Harlow and Luke running around  Eastern Long Island in sailboat prints, madras and sunhats? A toddler date in the Hamptons?

WHERE DO I SIGN????

Earlier this week, Seri and I invited our friend Dave Robbins (the brilliant photographer who took the Valentine’s Day pics) for a day out on the Island. We started with lunch at a classic Hamptons staple, the kid-friendly Sip-n-Soda.

Harlow and Luke quickly climbed the counter stools to show off their brand new duds.

Luke in his plaid button down and anchor shorts.

Harlow in a sleeveless top with matching shorts and scalloped sandals.

Then they waited patiently for their very first ice cream shakes.

Harlow requested strawberry but I instructed the server to ignore her and bring vanilla, since a mom always knows their child’s preferences better than they know their own.

Then Harlow refused to touch the vanilla and made it very plain that I HAVE NO IDEA WHAT I AM DOING and demanded strawberry a second time.

I will never doubt her again.

Next, we had a little wardrobe change and ran around the village of Southampton.

What? Your toddlers don’t change clothes in the middle of their play dates?

Harlow wore a fancy striped dress with a big red bow and declared herself a princess.

(Fabulous break!)

Then she added the best part of her outfit— a wide brimmed striped hat.

Harlow associates all hats with pirates and immediately transferred personas from Cinderella to Jake (of the Neverlands, of course).

We made sure to stop at the Southampton movie theater which always has a least one kid-friendly flick. That’s the theater Harlow’s big sis saw Planes, her very first movie.

Janie and Jack also supplied a pair of AMAZING sunglasses but Harlow refused to wear them with the hat, which will go down as one of my life’s most missed opportunities.

Thankfully, she had a change of heart at our next stop (and wardrobe change)— THE BEACH.

There Harlow paired the sunglasses with a sailboat dress but refused to wear the hat.

Although, she did love filling it with sand.

Luke wore his madras shorts with a roll cuff oxford shirt and loved filling his hat with sand too.

Here is an important note— if you ever want to take pictures of your kids, TAKE THEM TO THE BEACH. We spent a good hour debating whether to take the kids to a dock or the beach for our last photo op.

Hmmmm…. narrow walkway over murky water with toddlers who can’t swim….. or huge sandbox guaranteed to occupy kids for hours while they are sitting still???

Sometimes I wonder if I should have my parenting license revoked. Clearly, that should have been a much easier decision.

Not only did Harlow and Luke look ridonkulously cute at the beach in their matching Americana colors and preppy details (I am in love with Harlow’s dress), the two of them had the time of their lives.

I’d say I practically had to drag Harlow away kicking and screaming, but there was nothing practical about it. I literally dragged Harlow away kicking and screaming.

She even put on the hat to buy herself a few more minutes.

But seriously, we all had the best day.

My children will go on dates featuring adorable clothes ANY TIME.

If you’d like to shop all of Harlow and Luke’s outfits, visit Janie and Jack.

Also, if you hop on over to @mommyshorts on Instagram, I am giving away two $250 Janie and Jack gift cards just for tagging a friend (preferably the mom of your toddler’s main squeeze) and following @JanieandJack on Instagram.

Winners will be announced on April 24th. Good luck!

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And the winners are… @pepperandrocky and @cjpruelas

Congrats! Please contact abby@mommyshorts.com to claim your prize.

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All photos taken by Dave Robbins Photography