What To Wear To A Hamptons Winery: Summer Edition

Labor Day weekend is finally here and it’s time to relax, kick back, and celebrate the official “end of summer.” One of my favorite places to visit are the wineries. Wondering what to wear to a Hamptons winery? Keep reading!

If you’re anything like me, this time of year is a tough one because as much as I’m ready to embrace my cozy sweaters and PSLs. I get a little bummed about packing up the bright colors and patterns of the summer months. I work in media and have had to “labor on Labor Day” for the past few years, so this year is particularly exciting. I’m off and able to enjoy the holiday with Doug. His family has a beautiful house in the Hamptons and I’m especially blessed to be warmly welcomed into their home.

The Hamptons are one of my absolute favorite places to be.

I live and work in Manhattan, which is definitely an adventure every day. However, when you live in a concrete jungle, an escape is very necessary. Sometimes I’ll talk to friends who were born and raised in the city and the topic of the Hamptons will come up. Without a doubt, they all tell me someone in their family has a house “out east.” They frequent the location in the summer to soak up some sun and enjoy the feeling of grass in between their toes; unless you’re in Central Park, that’s a rare feeling.

When we aren’t on the beach, Doug and I frequent the wine country of Long Island on weekends

 Labor Day is no exception. There are about ten different wineries in the area and they’re very popular with bachelorette parties, sorority events, and couples like us that are just there enjoying the atmosphere. Our personal favorite location is called Osprey’s Dominion because they have live music on Saturdays (the musicians are seriously amazing). The lawn games such as KanJam, corn hole, and giant lawn Jenga, as well as the parking, is free! You can purchase a bottle or do a tasting at the bar to try a variety of different wines before committing. A solid choice if you’re indecisive like me.


Whenever we talk about going to a winery, Doug and I always joke about this one particular outfit we saw a girl wear a couple of years ago.

I had on a big floppy hat with a monogram on it and a floral romper that day (more about rompers and wineries if you keep reading). We’re drinking wine and looking around and I shout, (I’d had a few glasses) “WHAT IS SHE WEARING? Who wears leggings to a winery?” Granted it was June and granted I was a little buzzed, but to prevent being the “girl who wears leggings to a winery,” I’ve decided to share my greatest what to wear to a summer winery secret…

A romper. You can play all the games you want, sit on the grass and not worry about sitting with your legs to the side and (best of all) they photograph INSANELY well.


I absolutely am obsessed with this particular piece that I’m wearing. While I didn’t see it during the Lilly Pulitzer After Party Sale, this is one of my favorite pieces they put out all year (hello to any print featuring pineapples)! My ribcage is wider than I wish, so when it comes to buying rompers and jumpsuits, they commonly fit in the torso and waist and I can’t get them to zip in my ribcage. Solution: Lilly Pulitzer rompers. I’ve linked mine below along with my top picks in different styles. They insanely figure-flattering and look great on any body type.


Hi! I'm Emi! I love classic style, iced coffee, cupcakes and Broadway musicals. I'm a French Bulldog mom and live with my husband in North Carolina. Glad you're here!

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