what to wear in the hamptons

I Visited the Hamptons in Really Dirty Clothes

Last week, I was in the Hamptons. The too-good-for-you, too-rich-for-you Hamptons. I inhaled a $7 clam chowder like it was the last meal I’d ever afford and washed it down with an overpriced Monkey Fist IPA because apparently I’m into IPAs now.

More surprising than my recent affection for IPAs is the fact that I wore a lot of dirty clothes while in the Hamptons. It’s like I wanted people to know I didn’t make a nine-figure salary. I still can’t decide if I looked more like a cool broke writer or like an actual homeless person. Either way, it was very unlike me.


What Not to Wear in the Hamptons

Much like every other female who doesn’t know how to make decisions, I usually overpack for trips. But this time, I couldn’t. See, I was road-tripping up the east coast with my best friend. Her car was packed with stuff, and she said she wouldn’t have much room for my luggage. So I said sayonara to my favorite maxi dresses, told my boyfriend jeans “boy, bai,” and packed up the least amount of clothing I think I’ve ever thrown into a carry-on. While this is not uncommon for most seasoned travelers, I made the genius mistake to underestimate the need for real clothes while on this trip. I figured since there was a lot of driving involved, I’d only wear my workout clothes—elastic waistbands and oversized t-shirts for daaaays.

Boy, was I wrong.

Upon further inspection (and once in Orlando, our starting point), I realized I not only brought a surplus of weird, baggy tees, but I also managed to pack three “real” shirts. Two of them, still t-shirts, both white, with one signifying its independence with a bold “SUP” written across the chest. As for pants—I packed two pairs of interchangeable jean shorts and one pair of ripped black jeans.

Guess what I wore in the Hamptons? A white t-shirt and ripped black jeans. Every. Single. Day.

what to wear in the hamptons


What to Wear in the Hamptons

And apparently that is not the attire of Hamptons residents. If you’re wondering what the people who live in the Hamptons wear, I’ve got a treat for you. First, just so we’re clear—I asked a realtor I met just how much a house sells for in the Hamptons. After laughing and saying, “You don’t want to know,” he divulged: Even the crappiest house on the market would sell for just under a million (in the good areas). Otherwise, you’re looking at quite a few million bucks. And, remember, these are just people’s summer homes.

And while I was there during their off-season, the locals still hung around. One peculiar guy named Damar (name changed for privacy—I’m so0o0o nice) had toast-colored skin and a dark, curly man bun. He was probably creeping into his mid-40’s. His gait was lanky and exaggerated, something you wouldn’t (or would) expect from the man wearing a royal blue blazer, cropped white linen pants,  flashy loafers, and eccentric square glasses.

That’s what people in the Hamptons wear.

Damar waltzed up to my friend and I while we awkwardly stood in the corner of the bar where it turns into the restaurant. (We were sipping our drinks, waiting for another friend.) He blabbered on and on about how beautiful we were—did we know how beautiful we were?—and began shelling out unwarranted life lessons. Why do older people do that? They see two young blonde girls and think they are dying to hear the sage wisdom of strangers. All I see is a flamboyant dude hitting on me.


“You’ve Got A Great Look”

We do what’s best in this situation and use him for drinks. He’s already taken up a lot of our time because we’re too polite, so we let him buy us vodka lemonades and gin cocktails. He kept bragging about how much money he had, after all, so it just seemed like a good way to balance the juju in the world.

He’s chit-chatting my ear off at this point. I’m trying to do that nonchalant no-eye-contact thing to see if he’ll get the hint. He doesn’t. I think he’s on some kind of amphetamine. Amidst the shelling out of his wisdom, he barely asks what I do. I say I’m a writer, and he says, “Oh, fashion?” I tell him I do all kinds of lifestyle topics.

The SUP shirt I’m wearing has an unintentional couple of holes near the belly button. It’s not one of those expensive, destroyed tees—it’s just a poorly made garment I picked up in a Miami K-Mart. I threw on my favorite patterned bomber to offset the crooked seam and topped off the outfit with a glitzy Express necklace with a broken clasp. And, of course, my dirty ripped black jeans.

“I have a fashion magazine, you know,” he begins. My ears perk up, only because I want a job. “You’ve got a great look.”

If only he knew my entire outfit was under $75, shoes included. If only he knew my shirt was from freakin’ K-Mart.

(Recreate my cheap, dirty outfit with these pieces. It’s a “great look.”)

I’m being kind of a bitch to him at this point. Sure, we made a mistake letting him buy us drinks, but the drinks were really expensive and he wanted to do it. I think a lot of guys get some kind of gross validity from buying girls drinks—it’s the same thing every time: they act like they’re besties with the bartender, make sure everyone knows they’re ordering drinks for females, then barely tip at the end of the night.


People Are Idiots

I continuously cut him off from his weird life lessons with short, snarky remarks. I don’t care if I’m being rude anymore. At one point, I say, “I’m a writer, remember? All I do for a living is observe and people-watch.”

“So what is one thing you’ve learned about people?” he asks.

“That everyone’s pretty much an idiot.”

I don’t think he was expecting that. His already-cartoonish face became even more animated—it was hard for me not to laugh.

Eventually he walks away and we ask the bartender what his deal is. See, Damar kept inviting my friend and I to his pool party the following day. We would obviously never go, but it was so fascinating to hear this lunatic go on and on. He said he’d have hot guy models there for us. I was dying inside—he was serious! I told him I’ve worked a lot of fashion shows and honestly couldn’t give two shits. My friend and I even asked Damar for his last name because we wanted to Google him, because anyone worth something will show up in Google. Damar was nowhere to be found on the interwebs.

It’s amazing what people with money will say to feel good about themselves.

what to wear in the hamptons

The bartender said the guy was, in fact, a fashion designer (not a fashion magazine owner? Who knows.) and he does throw crazy parties. The bartender had been to a few of them. The bartender also said people would throw “key parties,” and I, the naive, endlessly curious darling that I am, asked what a key party was.

“Oh, it’s when they all trade keys. Like, house keys.”

I visibly and audibly shuddered at the thought of these rich people all swinging around in a cesspool of gold-plated diseases.

Damar also divulged that his magazine had folded, but all of his friends have fashion magazines. Oh, and he wasn’t there alone like we’d thought he was. His driver was there along with a fashion friend. The friend was a bald black man with supremely too-small circular glasses—a statement, I gather—and he hadn’t even tipped the bartender.

Like that hideous song by Real Housewife Countess Luann says, “Money can’t buy you class.”

I’ll take my dirty clothes any day.


visiting the hamptons

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