Stricken with grief and the need for a bit of distraction, Hollis Shaw (portrayed by Jennifer Garner) whisked four friends from different stages away to her beautiful home on Nantucket for a perfectly curated weekend. And, we all watched in envy—of the home and location, not necessarily of the conflicts that arise. The ladies of The Five Star Weekend packed their beach hats, cutest pajamas, espadrille wedges, and florals for a weekend of dance parties, shopping, delicious meals, and trying their very best to squeeze in moments of relaxation—and more times than not, failing to do so.
Naturally, as I watched, I considered what I would wear throughout a Nantucket weekend if anyone were to offer to whisk me away. I thought about which pajamas felt most suited for a dance party with the girls, which black look felt Saturday night dinner appropriate, and how I would want to look popping into local boutiques. Ahead, everything on my packing list for my hypothetical Five Star Weekend.
Friday: Arrivals
DÔEN Brielle Plaid Cotton Midi-Dress
While traveling to Nantucket, I would do my best to strike a balance between comfort and style. I would never want to feel uncomfortable while in transit, but I also want to arrive feeling good. This DÔEN dress is airy and offers a bit of stretch at the bodice and waist, and is in a fun, summery multi-colored plaid pattern.
Tieks Silver Screen Ballet Flats
These have unexpectedly become my go-to travel shoe—after the initial breaking in period, that is. A silver shoe makes just the right amount of a statement without overpowering a look or clashing.
Friday Night: Pajama Dance Party
Eberjey x The Ritz-Carlton Yacht Collection Inez Silk Printed PJ Set
Not only are these the comfiest pajamas that I own, but the blue and wavy lines akin to the ocean make these feel like quintessential Nantucket.
Saturday Morning: Shopping In Town
Farm Rio Beaches Path Printed Linen Mini Dress
This dress is begging to be whisked away to a beach town—just look at it. It feels like the perfect piece to throw on for a cute shopping in town—it's easy, but it's also definitely not boring.
TKEES Lily Flip Flops
These flip-flops are already a star in my real-life rotation, and I know they would come in handy more than any other shoes I own for a weekend in Nantucket. These would be a recurring character in almost all of my outfits.
Gentle Monster Dust Musk W2 Sunglasses
I recently learned that this is somewhat of a controversial opinion: I love white sunnies. These are the perfect square shape: not too slim and not too chunky.
Saturday Afternoon: The Spa
Gucci Floral-Print Lace-Trimmed Mini Dress
While the spa day was anything but relaxing for the Five-Star Weekend ladies, I picture mine unfolding much differently—and in a floral Gucci mini dress to boot.
Reformation Sonia Hat Bag
I've had my eyes on this Reformation bag all summer long—it feels like the beach bag and everything I would want in one. A practical size and a fun hat-shaped silhouette, this would quickly tie my daytime Nantucket looks together.
Saturday Night: Nice Dinner Out
Simone Rocha Bow-Detail Jersey Midi Dress
Having to wear all black to a dinner isn't a problem for me—my wardrobe is full of it. I would still, however, opt for something new if the opportunity presented itself. This Simone Rocha dress is so simple and yet so chic, with the bow details adding a bit of whimsy.
Larroude Gaia Low Sandals
The it-girl shoe of the summer and so easy to pair, these feel like my undeniable fancy dinner shoe.
Reformation Aurora Shoulder Bag
I love a statement bag. For the sake of adding a bit of dimension to my otherwise sleek black look, I wouldn't just reach for a beaded bag—I would reach for a printed beaded bag. We all know that animal print is a forever trend and that zebra print in particular is having its moment, so this feels like a no-brainer.
Sunday Morning: Fun Surprise
Reformation Eli Oversized Linen Shirt
If my Sunday morning is starting off with a beach stroll and chat with my bestie, I want to be in linen—that's just what I see for myself. I love the idea of this oversized Reformation shirt paired open and unbuttoned with the bra top below.
Skims Poplin Bralette
As a huge supporter of the bras as tops trend, this Skims bralette feels like perfect way of embracing the trend while still making sense for Nantucket.
Toteme Ramie Shorts
To complete the outfit, white linen shorts. I feel like this look is simple and easy, but the length and slight bagginess of the shorts make it look and feel a bit more like me.
Sunday Night: Make Your Own Pizza Party
AGOLDIE Shaw Jean
If we're making pizzas at home, I'm going to dress comfortably—and these are the most comfortable jeans that I own. They're relaxed and feature an elastic waist, so soft for the touch, and made out of an airy, lightweight denim essentially made for summertime.
Leset Slim Fit 2 Pack Tees
For an easy pairing, I would throw these perfect slim fit tees in my suitcase—both in black and white for the sake of variety. I would pair the black tee with the Agolde jeans for pizza night, and the white one would come in handy as an easy throw-on basic.
Monday Morning: Departures
Simon Miller Jabber Knit Pant
At the end of the weekend, I don't want to think too much about what I'm wearing—and at times like that, a two-piece set comes in handy. These Simon Miller knit pants are comfy, bold, and colorful and feel perfect for a chilly morning near the beach.
Simon Miller Mika Knit Long Sleeve Top
It wouldn't be a set without the sweater. For a look that is effortless but immediately makes you look put together, this is how I would travel home in style.
Chimi Lila Sunglasses
My sunglasses of the summer! They are perfectly oversized, and I feel like I can hide behind them when I'm completely exhausted.