What to Wear in the Hamptons

how to dress for surf lodge

Last week I had my first glorious taste of Hamptons living.  And while it was a vacation I cannot wait to recount in another post, I must confess that I had some serious pre-trip anxiety over what to pack.  At a loss, I did what any other self-respecting woman would do and turned to the world wide web.  But to my dismay, nothing of any worth popped up!  I couldn’t believe it.  Shouldn’t the internet be flooded with ‘Hamptons fashion’ posts?  Isn’t it a fashion bloggers paradise?

I mean here’s the thing.  I grew up in Cape Cod, but I’m so far from ever dawning a Lily Pulitzer print and I’m also not much of a Nautica and Sperrys chick.  I think this is a good time to mention that I wouldn’t miss the likes of J Crew, Vineyard Vines, Brooks Brothers or any other quintessential east coast preppy brand.  It’s just not my style to show up to a beach bar wearing the same Jack Rogers gold sandals and same Tory Burch clutch as every other chick there. Cringe.  But on the complete other hand, I adore playing dress up and curating a suitcase that seamlessly integrates me into whichever culture I’m visiting.

My real problem with the Hamptons though: Where on the scale from preppy east coast to trendy NYC chic was I supposed to fall?  I knew we’d be getting table service at the most bougie of places… but they’re on the water. Do I wear heels?  A hat at night?  A wrap dress and plunging neckline with a bunch of jewelry even though it’s 85 degrees with 100 percent humidity?  Are crop tops a thing here?

Right then and there, with my suitcase sprawled open and clothes everywhere, I made a few pre-emptive rules that ended up proving to be golden once I arrived.  And here they are:

Fashion in the Hamptons: 10 Rules

  1. Think in east coast hues.  Blues and whites, greys and some blushes.
  2. Stilletos will not do.  All heels should be chunky for the incredibly uneven terrain.
  3. Statement jewelry is a hell yes.  Big beautiful summery earrings and necklaces are perfect.
  4. No point in going if you’re not going to bring a whicker summer clutch. And an adorable sun hat.
  5. You can never have too much jean. Or as my mom would say, dungaree.
  6. Sweaters or a jacket for chilly night are a must.
  7. Bring your most fabulous swimsuit possible, you will be photographed in it.  Check out Amaio Swim for the most luxurious and flattering swim on the market (see below for reference pic!).
  8. Think daytime outfits that can carry over to night… just in case you don’t actually make it back home after mass-guzzling of frosé.
  9. Invest in a pair of cute neutral sandals – you’ll live in them on your trip.
  10. Don’t overthink it! There will be so much diversity in fashion at every single establishment you find yourself at… and that’s kind of the beauty of the place.  The Hamptons attracts the jet-setters, the trend-starters, the fabulous… but it also is sprinkled with a hint of sophisticated old money.  When in doubt, a confident smile is the best accessory anyway.  xxwhat to wear in montaukhow to dress for surf lodgehamptons style

OKAY, I did end up buying boat shoes, but they’re Aldo, not Sperry

Two other great accessories: Rosé & a gay best friendwhat to pack for hamptons vacation what to wear to montauk

fashion in montauk

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