I’m not going to lie, I thought the whole strawberry picking thing was lame and really just an excuse for influencers to pose for cute pics with their families. We’ve been apple picking with James. It was hot and dirty and his clothes were covered in mud within seconds. It took us an hour to get there for 15 minutes of apple picking and one crappy photo because he didn’t want to hold still. But it’s like that quintessential fall activity that you do because that’s what you’re supposed to do when your parents, and well, what else are we supposed to do once we can no longer go to the pool or beach every weekend? But then everyone started going strawberry picking this summer, and I felt annoyed by the pressure to do one more activity that I was convinced would be far better on Insta than in reality. But then friends of ours convinced us to go strawberry picking while we were in the Hamptons last week, and now I totally get the hype — it was awesome… for everyone. I previously rolled my eyes at the idea of getting dressed up in cute dresses to pick strawberries and after eating most of our spoils as we picked, I still do. However, I still feel like an Insta-worthy setting deserves a cute enough outfit to be photographed in, so I thought I’d share some ideas for what to wear strawberry picking (because really, I had no idea).
I’ll also tell you what not to wear strawberry picking: flip-flops like I did. In fairness, I wasn’t prepared to go strawberry picking and didn’t pack appropriate shoes for our Hamptons getaway. But I would recommend sneakers or even wellies, and really, even boat shoes would have been better. Basically, I’d wear closed toe shoes. But you know what, I wore flip-flops that I usually only wear to the pool or beach and I survived, although my feet were filthy and in need of some serious washing afterward. I think wearing cute matching outfits or sweet sundresses is nice in theory, but I like to go a bit more casual on outdoor excursions where I know I’ll get dirty, and I find it hard to believe that anyone can tromp through strawberry patches in a white dress and come out unscathed. I don’t want to be stressed if my kids wipe strawberry juice on me or if I get splashed with some mud while pulling them on a wagon through the fields. So I would recommend clothes that you don’t mind getting photographed in but that you also don’t mind potentially getting dirty. I chose my favorite denim cutoff shorts (seriously they’re the best), a simple white tee, and my favorite striped sweater — my classic Hamptons mom uniform that is perfect for playing with the kids apres beach. Even though it was a bit overcast when we went, I kept a hat and sunglasses on because I now know the consequences of sun damage (and that it can happen on cloudy days and there’s only so much Botox a person can get). In any event, I highly recommend this beloved Instagram summer activity (check out more ideas on my summer bucket list) and if you do go, here’s my recommendation for what to wear strawberry picking.