I jump around a bit in this post, so I’ll give you quick outline. It’s also a little long (too many pics!) so you may want to click over to the site/app to read it in full.
My trip to NY itinerary
Thoughts on boutiques, shopping, and my own internal crisis
Back to the itinerary
What I packed
Long Island, The Hamptons, The North Fork
My boyfriend and I went to NY for the long weekend to celebrate my childhood friend’s engagement, which was at her fiancee’s sister’s home in Long Island. We flew into LGA Friday morning and rented a car to get out to LI. Our home base for the weekend would be in Jefferson Port, but since we only had the afternoon/evening, we decided to drive straight out to The Hamptons. Neither of us had ever been to any Hampton (still not exactly sure what constitutes a Hampton) and we both have a love for the show Revenge (anyone remember that one?) so we were excited to explore.
Our first stop was in Southampton for lunch at the Southampton Publick House. We sat outside, survived the bees, and enjoyed a lobster roll and a Southampton Palmer.


After a quick stroll through the main street, we decided to keep moving. By this time it was already about 3pm and there were more Hamptons to see! Our next stop was Amagansett. Of the three towns we stopped in, this one was my favorite. It was full of the classic shingled buildings and homes, enough independent shops to feel special (more on this later), and all the hydrangeas you could ever want.



On the way back to Port Jefferson, we stopped briefly in Easthampton, and even though the town is beautiful and the homes incredible, it just wasn’t my favorite. I didn’t even take any pictures. I think if we had more time there I probably would have loved it, but it was about 6pm by this time and we needed to check into our hotel (about an hour and a half drive from there). My only regret is we didn’t get to Sag Harbor. I guess that means I’ll have to come back. :)
A little itinerary detour to talk shopping/small businesses
In Amagansett we probably stopped in a dozen or more shops. Leallo, Suzi Kondi, Sabah, Lazypoint, Il Buco Vita, Clare V, Botanica Bazaar, E-E Home, Ulla Johnson, Jenni Kayne, The Row, and Love Adorned are the ones I remember. These shops range from boutiques with a beautiful curation of relatively unknown makers and designers to brands that are still considered small but have made it to the mainstream, to The Row, a mainstay in luxury fashion. I left Amagansett with my head spinning, to be honest. Where does my brand fit? Where do I fit? What do I want it to become/ evolve to? Are we all just shopping the same brands and beginning to look the same?
My favorite of all of these shops (and the only place I bought something) was Lazypoint. It epitomizes what I love about shopping in person. Il Buco Vita also falls in this category, but I couldn’t take ceramics home with me! The owner of Lazypoint has a quirky, but beautiful point of view that comes through with what she curates for her shop. It’s a mix of vintage, new, all independent designers/makers, all handmade, all beautiful. I bought a really cool makeup pouch that I might end up using as a clutch or as a pouch in a tote bag. I loved it because I had never seen anything quite like it. Stores like these make me happy. I love the discovery process of shopping. It’s not about mass consumption, it’s about appreciating the artistry, the creativity, and the story.
My other favorite shop was The Row. I’ve seen The Row’s products online, on Instagram, in person at department stores, but never at their own store. The quality is apparent, but the point of view is what is striking. Minimalist, edited, and more edited. It drew me in - craving this kind of peace, clam, and sophisticated ease.
So what of the other shops? The Jenni Kaynes, Ulla Johnsons, and Clare Vs of the world? It made me chuckle that they have shops in Amagansett - they’ve really honed in on their target customer. If I’m totally honest, I don’t love perusing these places. Nothing against these brands - I actually own a couple pieces from Jenni Kayne that I adore. They are all beautiful in their own way. It’s not about the products, but about the way they are marketed and how oversaturated they feel (to me).
It seems like once a brand is everywhere, it’s not as interesting to me. It reminds me of high school when everyone had to have Sevens jeans or the Steve Madden platform shoes. We all start looking alike and there’s less room for personal style. It can start to feel like, “if I don’t own ____, I don’t fit in. Or I’m not cool.” Or any other lie we are tempted to tell ourselves. That’s not a line of thinking I want to entertain or promote.
But, it is interesting all of these stores are in this small town, Amagansett. And you certainly don’t find The Gap or Abercrombie there. These companies know where their target customers are, which is both smart on the brand side and helpful on the consumer side. After all, I love being able to shop my favorite brands in real life! I think I just miss the days where boutique owners were the curators, picking and choosing their favorite things from dozens of lines. It makes for a more interesting experience with depth and intrigue. Maybe that’s what influencers are now?
This whole day in Amagansett made me stop and think about my own brand and what my goals for it are. How do I grow and stay authentic? It also makes me reflect on my shopping behavior. It was a really inspiring and thought provoking day.
If you have any thoughts on this, please leave them in the comments, I’d love to hear them. :)





Ok back to the itinerary…
Saturday morning we drove out to the North Fork - Greenport specifically - for brunch and a stroll by the water. I really like the vibe of this town. I was here a couple years ago and it was just as cute as I remember. We had brunch at The Crazy Bean, which was delicious. There was another place called Pip’s that looked really good too. Next time! And per the conversation above, Greenport only has independent shops as far as I can tell, which gives it a unique charm and character.




There are loads of wineries and breweries on the North Fork, so on the way back we stopped at Jamesport Farm Brewery. It was a perfect afternoon. Live music, cornhole, good beer, and sun.


We then headed back to the hotel to get ready for the main event that evening. It was really special celebrating my dear friend and her fiancee and getting to introduce my bf to a few of my favorite people who don’t live in Chicago.

What I Packed
I tried to pack super light for this trip knowing we’d head straight from the airport to The Hamptons and were only gone for a little over 48 hours. In all I brought 1 pair of pants, 2 tanks, 2 layering sweaters, 1 blouse, 1 jumpsuit, 1 dress, and 3 pairs of shoes. I actually wore every single thing I packed, so I count that as a win!
Airplane/Hamptons Outfit:
Black Jumpsuit (old), White Eyelet Blouse (I could keep it on or take it off if it was hot), Flip Flops, Black Croco Sling Bag, Sunglasses1
North Fork Outfit:
White Pants, Tank, Sandals, Espresso Croco Sling Bag, Cakes (the only “bra” I brought with me)
Engagement Party Outfit:
Dress, Cream Cardigan, Crochet Bag, Wedges (not pictured and from a trip to Mallorca)
Sunday Brunch/ Airplane Outfit:
White Pants, Tank, Brown Cardigan, Sling Bag, Flip Flops
I hope you had a lovely Labor Day Weekend!
xo,
Abby
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I chuckled when you mentioned sevens jeans and the platform Steve Madden shoes… I remember those days! What a great point about people trying to look the same. I love the idea of getting inspiration from others but putting that into my own style. There’s something special about just being uniquely us :-) Thrifting helps with that for me :-) sounds like a lovely trip!