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Two-Piece Set (Gal Meets Glam) | Headband (Anthropologie) | Shoes (Soludos)

June is wrapping up and we are in the THICK of Hamptons season. When most think of the Hamptons, they think of Diddy’s white party, which isn’t totally inaccurate but there is much, much more to dressing for the Hamptons. Unlike what most people would think, the Hamptons is actually a super casual environment. Jeans (even ripped) are pretty much acceptable everywhere and you find many slumming around in shorts and flip flops.

Today, I’m here to help you for being THAT person who sticks out like a sore thumb. You can always spot the Hamptons newbies from a mile away (and not in a good way). They are either A) WAY too dressed up or B) taking preppy to the next level (seersucker galore, sweater looped around their neck, etc.).

As a Prepster myself, I’ve had to reign in my New England summer preferences. Unlike somewhere like Martha’s Vineyard, Nantucket or Cape Cod where you can find seersucker, polos and Lilly Pulitzer around every corner, you have to remember that the Hamptons are after all populated by Manhattanites so you’ll find plenty of urban styles (think blazers with in a clean linen instead of black or navy).

As a natural Prepster, Hamptons style falls somewhere in the middle of metallics and Lilly Pulitzer. When getting dressed in the Hamptons think, cool (because there are plenty of places with no or limited AC), elegant (conservative but still summery) and comfortable (remember, you’re still on vacation!). Below are my 5 tips for packing for the Hamptons:

1| A casual but elevated pair of shoes. If you ask me, I advocate for comfort over EVERYTHING but you still want to feel refined so don’t be brining your Old Navy rubber flip-flops. If I’m headed out for the weekend, I usually only need two pairs of shoes. One pair of Jack Rogers for during the day and my Soludos espadrilles for the evenings.

2| Prints & Florals. Honestly, this outfit featured in this post is basically the perfect Hamptons outfit. The pastel floral print is super elegant while the short and cropped top combo is super casual and great for any dockside dinners. In addition to this two-piece, Gal Meets Glam has plenty of other appropriate options. And I can’t rave about the quality of the brand enough!

3| Hair accessories for all types of weather. The weather in the Hamptons is SO unpredictable. It can be raining cats and dogs one minute and suddenly turn into the most beautiful night of the year. As someone who has some of the most unruly hair ever, I always have hair accessories to make it more manageable on hand. Now that headbands are officially back in style (YES!), I’m a huge fan of the top-knot headbands. I wore this white one from Anthropologie multiple times throughout the weekend. I also recommend a set of barrettes to mix it up a bit.

4| All linen everything. This weekend, I wore linen not once but twice! I threw on a pair of linen shorts for brunch at the Hampton Maid on Saturday and then this linen two piece of Saturday night dinner at Dockers. This tip pays off on all three of my criteria. There is no cooler, more elegant or comfortable material you can find.

5| Your favorite par of sunnies. I mean, this one is a bit of a no-brainer but very, very necessary. Even though I’m the first to sleep in on vacation or even a general weekend, that doesn’t happen in the Hamptons. I love waking up early, grabbing a cup of coffee from the kitchen and spending the entire (and I mean entire) day outside. I few of my current favorites is this retro-inspired style and these over-the-top cat eyes (currently on sale! Use THEPREPPYMAG15 at check-out for an additional $15 off).

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Need more inspiration for an upcoming weekend out east? I’ll be headed back out to the Hamptons for the 4th of July and sharing all of my outfits here on Instagram. Be sure to follow along for a constant stream of inspo.