A Weekend in Sag Harbor - Among Other Things

A Weekend in Sag Harbor

This past weekend, you guys, I did something that I haven’t done in nearly a year. And it felt good.

white eyelet shorts

I… drove a car.

(Sorry if you were expecting something a little more salacious, but today’s story will still be fun!)

Yep – a year’ish.

Living in the city simply tends to have that effect on you, though – I never needed a car in Chicago and I certainly don’t want to deal with parking here in New York (not to mention the lack of actual space). I was traveling in Asia over the holidays last year and my family generally doesn’t trust me to drive when I come home otherwise — not that I can blame them.

antiques-shop-hamptonsantique stores in the hamptons

So last Friday, I drove. I hopped behind the wheel of a super-sleek Cadillac CTS (which the brand let us borrow for the weekend) and embarked on a small-town escape to Sag Harbor with my ladies Jess & Lauren.

Now, let me clarify: I AM a good driver. It’s just been awhile, so I was simply one of those who essentially sits on the steering wheel and prematurely uses the blinker — even when there are no cars in sight.

Driving in New York City will make you re-think your entire outlook on humanity. Like, are we all morons? Seriously. Phone-in-hand pedestrians are absolutely oblivious. Cab drivers do whatever the hell they want and it’s a known fact that bikers own the road. Holy smokes.

Once we emerged from the congestion of the city, though, it was smooth sailing – er, steering. Off to Sag Harbor we went!


If you’re unfamiliar, Sag Harbor is a close-knit Hamptons community located two hours outside of Manhattan. (Or closer to four if your co-pilot enters the wrong address in the GPS and you pit stop at, say, a Wendy’s for Frosty’s and french fries. Hypothetically speaking.)

The three of us stayed with the Cadillac crew at a charming tree house-inspired cottage in a quiet, back-roads kinda neighborhood. My most pointed memory of the weekend (oddly enough) was laying on the wrap-around deck, rosé in-hand (bag of tortilla chips in other hand), drunkenly admiring a sky full of stars. I hadn’t seen stars in awhile.

Both mornings, we drove into town to wander along Main Street, which curves away from the harbor and boasts an array of art galleries, vintage clothing stores, antique furniture shops and restaurants.

coffee shops in the hamptonscoffee hamptonssagtown-coffeesag-harbor-coffee-shop-hamptonssagtown-coffee-juice-bar page-sag-harbor montauk yacht club

At night, it was all about the high-powered Hamptons experience.

We were fortunate to attend a slew of events with the brand, as Cadillac was sponsoring a weekend-long partnership with IvyConnect, which is a members-only social network of local entrepreneurs, business leaders and other accomplished professionals.

The festivities included pool-side parties, sunset cocktails at a private estate (note to self: marry rich), and one hell of a fundraising fête (to benefit Building Blocks for Change) on Saturday.

keds flatschunky navy blue sweaterchunky sweater white shorts

I pretty much wore this cropped sweater, a pair of white lace shorts and Keds sneakers all weekend, but I packed a pair of stacked sandals from J.Crew and a brightly-colored drop earrings to dress up my more casual duds.

In sum, lots of beautiful people, lots of beautiful cars. Loooots of rosé .

Which brings me to today — lots of concealer (yes, still). Loooots of water.

ysl rogue lipstickdesign-darling-earringsnude platform sandals

*Wearing: 525 America cropped sweater (had to buy it in white, too), Joe Fresh shorts (identical pair here), J.Crew sandals (extra 25% off with code ALMOSTFALL), Lisi Lerch drop earrings c/o Design Darling (finally back in stock!), Ray-Ban aviators

*SHOP MORE: J.Crew shoes (all on sale), this post (below):


Sag Harbor photography by Hallie Wilson
Outfit photos taken by  Jess & Lauren

Join the Convo:

  • So funny that you make the comment about the stars—since I’m back in the midwest this week, I was looking out the car window at night while my mom was driving and realized I hadn’t seen any in months. Naturally, she teased me, but it was nice to gaze for a while! Also congrats on your first time driving through Manhattan, my first time was last year and it definitely makes me a more conscious pedestrian for a few days after each time I do, ha!

  • Haha that is so funny – but I guess you don’t need a car, huh? So fun! Love those lacy shorts!
    PS – Thanks for passing my email to the right person! : )


  • I wish I could ditch my car, but that just doesn’t seem possible here in Kansas City! p/s your weekends sound so top notch!

  • Love love love those shorts, btw! And I think it’s hilarious that you mentioned New Yorkers and how oblivious we are. I drive a car, but am also a pedestrian — soooo I see both sides of the argument;)

    Dana | Pink Champagne Problems

    • Ditto here, ha! I (we) will forever be so much better about multi-tasking while walking.

  • you look so cute! Sag Harbor remains one of my favorite getaways.

  • Looks like a fun weekend!! And I love your outfit girl!!

  • Meagan

    What a fabulous weekend! Looks like you had a blast!

  • This sounds like the perfect weekend – I’m looking forward to loooots of cocktails this weekend, too. Glad you got to take a little vacay! xoxo

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  • Since moving to the city I have not driven either! I’m actually kind of terrified of when I NEED to drive ay ay ay. Sounds like you had a great time!

    Xo Miriam

  • Sounds like a great weekend! I’m way too much of a Miami driver to drive in NYC. We don’t have to worry about pedestrians all too often, so when we do someone in the car usually yells, “C’mon, bro, move it along or you’ll be another 500 points!” #GrandTheftAutoGeneration

    Love how you mentioned stars. I had the same reaction when I saw stars after spending a year in the Bronx. I kept asking if the stars and mountains in Northeastern PA were real or just satellites and trash hills. (I’m from Miami, our hills aren’t real)

  • Great photos Hallie! Love that one in the car with the lipstick!

  • You look gorgeous, Hallie! Everything looks picturesque and perfect 🙂 Glad you had so much fun!

  • you are so cute <3 i adore this! haha my boyfriend doesnt trust me to drive either!

  • Sounds like a fabulous weekend! Love those shorts & sandals! I wish I didn’t have to have a car in Seattle, my blood pressure would probably be a lot lower. (I may or may not be a ragey driver 😉 )

  • Okay your, “My most pointed memory of the weekend (oddly enough) was laying on the wrap-around deck, rosé in-hand (bag of tortilla chips in other hand), drunkenly admiring a sky full of stars. I hadn’t seen stars in awhile” sounds like the PERFECT night. Frankly, anything involving tortilla chips is my kind of party.

    Love your pictures! Your trip looked awesome!

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