Okay… so this weekend started like any other – with the usual “I have nothing to wear” meltdown followed by trying on five different outfits and ultimately leaving the apartment in the exact same jeans and blazer I wore last weekend. But hey, it’s called effortless chic for a reason, right?
Well. What happened next? Was not planned. But maybe… maybe it was meant to happen? (Dramatic pause.)
It All Started with a Margarita…
I was walking through Soho after a very leisurely brunch at Jack’s Wife Freda (try the chili-lab shakshuka – thank me later). I had no real plans for the afternoon, which was honestly kind of glorious. The sun was doing that late-June golden thing and I felt like I was in a movie. A very stylish movie where the main character wears impractical shoes and has zero sense of direction (hi, that’s me).
So I’m sipping my iced lavender latte, and I hear music. Not just “someone is playing a Spotify playlist in their fourth floor walkup” kind of music. This was full-on rooftop vibes. There were voices. There were laughs. There was a saxophone. Naturally, I craned my neck like a tourist and scanned the skyline.
Then I saw it.
People. On a roof. Dancing. Clinking glasses. Wearing sunglasses that said “I know I look good.” My curiosity was piqued. (Possibly also my FOMO.)
So… I followed the music.
How I Ended Up at a Party I Wasn’t Invited To
Okay so in my defense, the front door was already open. I didn’t sneak in, exactly—more like… confidently wandered.
The elevator had charm (i.e. it was old and slightly terrifying), and when I reached the rooftop, I thought, “I’ll just take a peek.” Cut to me standing there like someone’s intern who got lost on the way to pick up oat milk.
At first, no one noticed. Then a very tall guy in linen pants offered me a spritz and said, “You made it!"
And here’s the thing.
I could’ve corrected him. Could’ve said, “Oh no, no, I don’t belong here, I’m just a woman who followed the saxophone.” But instead I just went with…
“Right? Traffic was insane!”
Who even was I?
OKAY, Technically, I Crashed the Party…
But I also met Serena — a French fashion photographer who splits her time between Paris and Brooklyn (ugh, rude). She wore a backless slip dress that somehow didn’t move at all in the wind?? Anyway, she told me my earrings were “decadently charming” and now I want to cross-stitch that phrase onto a pillow.
I also talked to this guy named Mateo who makes pottery and sells it at the Union Square Greenmarket. I told him his forearms look like he lifts artisanal clay bricks, which might’ve been a weird thing to say, but he blushed — so let’s call that a win.
We talked about everything from vintage denim to the existential pressure of having an Instagram aesthetic. I know, deep.
By 7 pm, I realized I had completely ghosted my original plans (sorry to the group text) and had now RSVP’d "yes" to someone’s afterparty in Williamsburg with my new rooftop crew.
What I Learned from My Accidental Rooftop Adventure
Besides the fact that I apparently have no shame and will accept cocktails from strangers on a random rooftop, I realized something about the city (and about me — thank you, rooftop reflection moment):
- You never know where the day will take you.
- Saying “yes” can lead to ridiculously fun, unexpected places.
- Rooftop parties are peak New York and should be treated like limited-edition handbags — rare, fabulous, and worth the risk.
- Always wear good earrings. You never know who might call them decadent.
So… Would I Do It Again?
Absolutely. Do I recommend it? Um, yes — but with street smarts and a backup plan in case you run into actual strangers and not just a bunch of Brooklyn creatives who assume you’re a plus-one. (Thank you, linen pants guy.)
This is why I love New York. It’s loud, unpredictable, occasionally smells like bagels and despair, but it’s also kind of magical. You wake up thinking it’s just Sunday — and you end up dancing on a rooftop wearing somebody else’s sunglasses and promising to meet for French toast in Dumbo.
Stay spontaneous. Stay overdressed. And always follow the music.
xo,
Rachel 💋
“Life’s too short not to crash a party or three.” – Me, just now.
