This year marks our eleventh summer soaking up the sun, enjoying the fresh hydrangea, and eating all the lobster rolls on Nantucket. Per usual, I overpacked (lol), and we managed to capture so many incredible moments on the Grey Lady. Typically, my Nantucket outfits consist of endless dresses and maxis. This year, I brought a few more separates, some great swimwear, and more hats than ever!
How I Packed My Nantucket Outfits
Surprisingly, we managed a bit more than a week’s worth of clothing and necessities in two checked bags and two carry ons. Naturally, I had to make use of the luggage I designed with Mark & Graham. Plus, the travel tote, packing cubes, watch roll, and jewelry cases were a must. Another carry-on I adore is the new Steamline x The Hamilton Princess Bermuda bag. The pink is even more lovely in person!
Shirt: Talbots Button Down | Pants: Southern Tide Laken Wide Leg Pant {also worn here} | Sweater: Tutto Knit Light Blue Berry Stripe Sweater | Jewelry: Lisi Lerch Barrett Studs | Shoes: Castañer x Charo Ruiz Eyelet Espadrilles | Luggage: Mark & Graham x Jennifer Lake Carry-on Luggage | Bag: Mark & Graham x Jennifer Lake Avion Travel Tote
Traveling to Nantucket
Words cannot describe how thankful I am to United for continuing their direct flights from Chicago to Nantucket. Granted, it’s only in the summer months (and only on weekends). Regardless, we’ll take what we can get. Over the past decade, we’ve taken almost every route to the island including Cessna planes from Logan Airport via Cape Air, regional connections in Newark, Boston, D.C., and Providence. Plus, we’ve made use of the high-speed ferry countless times through Hyannis in order to avoid less-than-ideal summer weather that would have otherwise delayed a flight.
When referring to traveling to Nantucket, our friend Mackenzie puts it best: “the juice is worth the squeeze.” Thankfully, with these direct United flights, the squeeze is far more bearable!
Earlier this year, Allie Provost texted me a link to this bag and said, “we have to buy this one for Nantucket!” She was right, as it sold out so quickly! When I stumbled upon this hydrangea print mini dress, I knew it would be a perfect match for the novelty bag. Plus, it made for a fun moment on the island!
Recently, Veronica Beard debuted their line of sunglasses. When their team reached out to see if I’d be open to bringing a pair to Nantucket, it was an immediate yes! I was torn between the classic tortoise pair featured here and these stunning aviators. Since the aviators are on pre-sale, the tortoise were the best ones for me! They’re classic, comfortable, and available in three colors.
If you’ve ever been to Nantucket, you know it’s an active island. From bike rides to Sconset, long Bluff walks, and pickleball, most residents and visitors love to stay healthy. This WISKII tennis dress was a no-brainer for my packing list. I love the integrated and removable bra pads and how it comes without shorts so that you can pair the look with your favorite pair.
Early during our trip, Allie hosted a lovely lobster bake at her rental. It was such a fun evening, and I loved catching up with friends who were also on the island that week. This FARM Rio set was perfect for the evening, as it ended up being a warmer and more humid day. I found the pieces to fit true to size. Also, I’m 5’4″ and wore flats, so you have a better sense of where the skirt hits on someone of my height.
One thing our rental had that sealed the deal? A private courtyard! The loungers made for a relaxing spot to read in the sun. Plus, Bob loved the grill and outdoor dining table for homemade meals al fresco. Two books I brought for our vacation were The Wedding People and One Golden Summer. I finished the first and really loved it – a perfect summer read set in Newport. I’m in the midst of the second one, and things are heating up, lol!
A few months ago, Christy Lynn and her team floated the idea of me hosting a dinner with them in conjunction with the Marissa Collections summer pop-up in Town. Needless to say, it was a no brainer! Over the years, I’ve loved and worn her designs (like this set during our Montecito trip and this stunning jumpsuit years ago). The evening was so incredible, and it was beyond lovely to spend quality time with some of my favorite ladies on the island (and for many of them to meet each other for the first time!).
Last year, I made the plunge and bought a Nantucket Lightship Basket from Four Winds Craft Guild. Mine was made by Bill & Judy Sayle, and I added an hydrangea scrimshaw to the top (an homage to my mom), along with a plaque bearing my name on the inside. Since 2024 was the ten year anniversary of our first trip to the island, this heirloom-worthy purchase seemed fitting.
This summer, CJW hosted a few pop-ups on Nantucket where they sold the brands chic pajamas, darling loungewear, and iconic scarves. I snagged this Summer Friday set – it’s so comfy and well made. They also have an exclusive Nantucket print, and the pajama set in the print is available exclusively at the Sconset Casino pro shop. They are sold out but taking pre-orders for an August delivery. See details of the Nantucket print here!
When I first saw this incredible ombre dress, I knew it needed its moment in the sunset! I’ve adored Mestiza NY dresses going on ten years, and this summer’s collection is phenomenal. Fit note, I find their prices tend to run just a touch small (especially in the bust), so feel free to size up if you’re unsure.
I first met Gabi of The Preppy Stitch a few years ago at a New England Coastal Creative conference. She is such a gem and so talented. She held a few pop-ups on the island this weekend, and I managed to snag one of her coveted East Coast Summer embroidered totes. This is the mini size and perfect for essentials.
I first spotted this Benaar LA set on Meeghan Mullin, and it’s even better in person. It fits beautifully, and the fabric quality is really great for the price. The wrap skirt only fastens at the waist, so be mindful of windy days, lol!
There’s nothing better than when all the roses are blooming in Sconset. This easternmost part of the island is known for their iconic cottages and stunning summer florals. Plus the Bluff Walk, the beach, the Sconset Market, and other restaurants makes this part of the island worth a day trip. We rented a home here last year, and the slower pace of things was just what we needed!
Speaking of the Sconset Beach, this is one of our favorite spots to relax and catch a few rays. It tends to be on the quieter side and a great place to catch sunrise or enjoy the morning. Head up the hill to grab a blueberry muffin at the Sconset Market, and you’ve got yourself a perfect start to the day. I found this one-size-fits-most stretchy swimsuit at Shopbop, and my almost-20 year old L.L. Bean Boat & Tote was perfect for a morning listening to the waves.
Most years, we try to go on a sailing excursion with Endeavor Sailing, and this year was one of the smoothest sails in memory. The weather was warm, slightly overcast (classic for the Grey Lady), and the waters were incredibly calm. I was inspired by Liza Kameen to get this dress and sweater, and both proved perfect for the occasion. If you’re in between sizes, I say go up a size in the dress (the fabric is sturdy without much give).
Stay tuned for part two of my Nantucket outfits!