The Perfect Nantucket Wardrobe Fits in a Weekender Bag

One of my favorite parts about living in New England is being able to easily bop around to various other coastal towns on easy, mid-week summer jaunts. While admittedly most are just variations on a theme, each seems to have its own unique charm and hidden gems to discover, which provides a great change of scenery without having to travel very far or do much planning. To maintain a moderately low-stress life, I like to avoid airports whenever possible! I recently jumped on the ferry to Nantucket for the first ever time this June, which absolutely lived up to the hype. While I am not new to dressing for a northeastern coastal summer, I will say I somehow packed pretty perfectly to look the part and also be ready for any quick changes in weather—I never felt unequipped. Bookmark this page for a foolproof wardrobe that all fits into a weekender bag. Here’s what I wore for my 48 (gloriously childfree, might I add) hours away in Nantucket.

Day One: My Arrival Ferry Fit

Secondhand Junya Watanabe striped terry sweatpants in the shape of “jeans”, a navy blue &Daughter sweater, and trusty Sperry x Aritzia boat shoes were the perfect comfort-forward outfit for a chilly June morning on my way to Nantucket. I snapped a pic for my arrival so my driver could spot me easily for a smooth pickup downtown. I later stripped off the sweater to reveal just a simple tee underneath for exploring downtown after dropping my bags off. However, the sweater and boat shoes remained crucial for the rest of my trip, since a New England June is highly unpredictable, and I worked them into my outfits a few more times.

Night One: Sunset Cocktails and Chilly Boat Ride

I presto-change-o’ed into Massachusetts-based Mahi Gold’s one-shoulder, long cotton dress in a navy and white gingham print that seamlessly went from cocktails at the house and into a misty boat ride with just the addition of a few layers. I carried my Vineyard Vines straw bag in the shape of a nautilus straight from cocktails to the boat ride but then added my &Daughter navy sweater, a Max Mara parka, and go-to Maggie’s Organics cotton socks under my boat shoes for weather-ready layering that luckily was easy to shed once the sun came out right before dinner at Breeze inside of the Nantucket Hotel (pro tip: don’t sleep on the bread pudding for desert!).

Day Two: Yoga and Brewery Lunch

It was a chilly morning for a private yoga sesh with @yoga.with.emmy, so I wore a vintage Gap long-sleeve tee from my secondhand shop, Stripes Newport, with simple black cotton leggings and a pair of Oofos recovery flip-flops to easily slide on after my workout. I loved the ’90s surfer vibe of the outfit, which felt pretty right, and I couldn’t stop wearing my Vineyard Vines shell bag, so I threw it on again, adding another layer of classic Nantucket with a woven-bag touch. I had lunch at Cisco Brewery, which is fun because there are a bunch of food trucks to sample and share. I am still dreaming about my combo of the daily special sausage pizza from Eat Fire Pizza, the mac’n’cheese egg rolls from Nantucket Lobster Trap Truck, and the Puckernuck sour beer from Cisco. After lunch, I went shopping in town to grab a few souvenirs: a patch from Dairy Boy for my Summer 2026 tote bag I’m decorating with all of my adventures and a Nantucket Reds bucket hat from Murray’s Toggery that somehow matched my long sleeve perfectly.

Night Two: Farewell Dinner and Drinks Out

I wanted to be comfy but also covered up for a chilly night out downtown, which started at Straight Wharf Fish (smashburgers are a must!) and ended with obligatory mudslides at the Gazebo to toast to our last night on Nantucket. I threw on a secondhand Comme des Garçons embellished striped tee, a white linen Reformation a-line maxi skirt, a cardigan from FloreFlore, a pair of Reebok Club C’s I customized with ribbon laces and charms, and of course, my straw Vineyard Vines bag again. Sneakers were a wise choice for standing during cocktails and navigating the cobblestone streets. It was the perfect outfit for anything on our last night on the island.

Day Three: Bike Ride to the Beach and Ferry Back

The sun finally stayed put on my last day in Nantucket, so I threw on a comfy gauzy cotton mini dress from Vineyard Vines, a go-to oversized striped Gap shirt, Saba fisherman sandals, and my newly acquired Nantucket Reds bucket hat to jump on a bike down to Cisco Beach. The water was still a little chilly for a dip, but it was a gorgeous morning at the beach. I begrudgingly threw on a pair of baggy jeans under my dress for the ferry for an extra layer and departed the Island with happy tears in my eyes. Before I jumped into my car home, I grabbed one last Cisco beer at the ferry dock on land to capture the essence of my fabulous getaway.