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PACKING LIST:

Everything for Your Labor Day Weekend Adventure

By: Sarah Elson
Published On: 8/28/26
Three-panel fashion photo collage of a woman with curly hair in casual summer outfits at different outdoor locations.

Summary

•Labor Day Boat Ride Look: White Tee & Denim Cut-Offs
•Labor Day Sightseeing Look: Oversized Tee & Silk Shorts
•Labor Day Night-Out Look: Off-The-Shoulder Top & Trouser Jeans
•Labor Day Beach Look: All-White

Crisp white tees, slouchy denim, and vintage accessories make the perfect LDW outfit.

Labor Day may signify the unofficial end of summer, warm weather, and relaxing getaways, but that doesn’t mean we can’t enjoy one last hurrah. After all, it’s a great opportunity to indulge in a favorite pastime: crafting new outfits to celebrate a long weekend.

For my own personal adieu, I set out for Newport, Rhode Island, for sand and sun (and most importantly, lobster rolls). And with one clear goal (one that was different than the actual goal everyone has when they take a much-needed vacation): to create a capsule-inspired wardrobe filled with my favorite FP essentials, perfect for a getaway or Labor Day Weekend celebration.

My color palette: white, denim, and blue, also known as the unofficial uniform of New England–a fact I learned from a previous trip to Maine, and after tirelessly researching “Rhode Island outfits” on Pinterest. After stepping out of the car, I walked through town and along the wharf; it was a sea of cool tones, crisp hues, and effortless styling. There wasn’t a single person who ventured outside this unspoken New England dress code.

DAY ONE: OUR ARRIVAL

We set up camp at an inn just a short walk from downtown. After checking in, the innkeeper asked us if we were ok with stairs, a foreboding question. Cut to us schlepping our four suitcases (we were only staying four days) up the three flights of stairs that led to our cozy, albeit dark and a little damp room. Once we had unpacked and relaxed a little, we got ready for our much-anticipated expedition.

For the Boat Ride: White Tee & Denim Cut-Offs

For our first excursion in Newport, I planned a sunset boat ride. This was the event that would kick off our trip, and it was the perfect opportunity to get the lay of the land (or, I suppose, the sea). We arrived embarrassingly early to the dock, and to kill time, the tour guide suggested we take a stroll along the wharf and explore the shops. Laughter, music, and matrimonial merriment poured out of the restaurants and pubs interspersed among the trendy shops and tourist traps. A cab driver would later tell us that the inlet town hosted more than 40 weddings every weekend during the summer season.

Once we finished shopping and people-watching, we joined the other sightseers on the ship. According to the company’s website, the ship in its previous life served as a lobster boat. Little details of the ship's past life were apparent around the hull: a life ring hung next to the helm, old lobster cages fashioned into seats, and antique but well-oiled wooden slats encased the boat's outer shell. It was obvious that the tour guide loved his job; as we sped along the water and admired the rolling coastline, he peppered us with fun facts and quips about the beautiful seaside town. We cheersed to the occasion with complimentary champagne and raised our glasses for several birthdays and anniversaries.

My outfit for this trip: cute, casual, and comfortable enough to withstand a trip into the water (I was plagued with worry about my girlfriend falling in; she can’t swim). On top I turned to the We The Free Atlas Boat Neck Top, a soft cotton staple. On the bottom, I wore the We The Free Moxie Barrel Shorts, the cut-off version of our fave jeans. To keep the outfit classic and follow the town's timeless style, I accessorized with a vintage scarf and a basket bag that reminded me of the old sailing ships dotting the water.

Once we docked, a little windblown but warm from our complimentary drinks, we were drawn like moths to a flame to the live music drifting from a bar near the wharf. Unwilling to pay the bar’s cover charge, we spent the rest of the evening dancing outside the bar, twirling each other under the bright moonlight.
Three-panel image: woman in white top and headscarf on boat, house on rocky island in water, woman with woven bag at marina.

DAY TWO: EXPLORING

For the Museums: Oversized Tee and Silk Shorts

Even though Newport is a New England town, it felt as though we’d suddenly fallen toward the equator thanks to an unrelenting heat wave. Our in-window AC unit was working overtime to compensate for the unexpected change in weather. With our brains firmly on vacation time, we realized we had overslept. We raced to get coffee before our appointment at The Breakers, a Gilded Age mansion once owned by the Vanderbilts and now a historic site. Even at the early hour, the sun beat down on us as we waited in line for a much-needed dose of caffeine. After filling our stomachs with an exorbitant amount of pastries, bagels, and people-watching, we rolled ourselves into a cab. The driver, a local and impromptu tour guide, regaled us with the history of the town and mansions we were about to tour. It was clear he had given this spiel to other tourists, but we sat back and gracefully listened, enraptured by the image he was painting.

As we stood outside the impressive stone-and-wrought-iron gates that protected The Breakers from the outside world, we were stunned into silence. The house was indescribable. Impeccably maintained bushes and trees dotted the grounds in front of the mansion. A winding, rock-covered road snaked up to the house, almost as if they had rolled out the red carpet for the grand house in front of us. A gatehouse, designed with rows of windows and green-tinged ornamental ironwork, decorated the place; it served as the “ticket booth” for the grand home behind it.

Once we checked in, we were free to roam both the house and the surrounding grounds. We meandered through the interconnected rooms and servants' quarters that had once housed the most opulent and influential family in the country. Private rooms larger than my studio apartment, wall-to-wall marble bathing rooms, wood-paneled hallways, ceiling murals that were second (maybe) to the Sistine Chapel.

I knew we would be walking a lot, and the overbearing weather inspired me to don the We The Free Perfect Oversized Tee. To maintain the easy, laid-back look and elevate my outfit while keeping that effortless feel, I added the Meet Me In The Middle Tap Shorts. The silky fabric, combined with the oversized tee created a relaxed, juxtaposed look that made traipsing through Newport's old mansions a cool and delightful experience.

Once we were thoroughly full of opulence, and the previous night’s escapades had caught up to us, we left to enjoy a relaxing lunch.
Woman with curly red hair wearing white crop top and burgundy shorts with lace trim, posing outdoors on sunny day.

For A Night Out: Off-the-Shoulder Top and Trouser Jeans

As the sun dipped below the horizon, the weather cooled, creating a breezy, soothing evening by the water. Our plans were to enjoy good eats, drinks, and company. Outside the restaurant, groups of people eagerly waited for a table. We breezed past them all, an air of superiority exuding from us as we had the wherewithal to book a reservation ahead of time. Like most of Newport, the eatery was an old, restored home transformed into a high-end restaurant. As we climbed the stairs, it felt like we were arriving at an old friend’s house for a casual dinner party.

Once we were seated, we pounced on the menu. As self-proclaimed foodies with years earned in the restaurant industry, we were prepared for this. We fired off drinks, appetizers, and our mains, politely thanking the server who guided us through the menu. Decadent dish after dish arrived at the table, and we feasted among the mood lighting, low synth music, and other chattering patrons.

After a day of slouchy silhouettes, I wanted to focus on creating a uniquely structured look for our night out. I was drawn to the We The Free In My Element Tee for its fitted bodice and loose bust. To create some balance with the top and add some warmth to the outfit, I reached for the We The Free Golden Hour Trouser Jean. With its barrel-style leg and trouser-inspired look, it created a playful silhouette that worked perfectly with my thrifted heels.


Live music drifted from every bar along the wharf, each melody enticing us to join in. As we walked to our after-dinner drinks, which were a natural part of a night on the town, I put my best foot forward with cuffed jeans and vintage kitten heels.
Woman with curly hair in black top and light jeans posing by stone planter with white flowers at outdoor shopping area.

DAY THREE: BEACH DAY

Even though it was a little cooler than the previous day, after a night on the town, a relaxing day lying by the water was a must. Suited up, we packed the car with chairs, beach towels, snacks, and an umbrella (a vital essential for someone with my fair skin).

For those who don’t know, parking in Newport can be a nightmare. We triumphantly fought off the crowds of locals and tourists and parked ourselves in a primo spot by the water. Off-loading the beach necessities somehow proved harder than finding parking, and we were weighed down as we hobbled to the water's edge.

Fine sand slipped through our flip-flops and was unceremoniously kicked up behind us as we searched for the perfect spot to stake our claim. Once we had finished setting up, we eagerly opened our snacks for the excursion. With what seemed like comedic timing, we were overwhelmed by seagulls who eagerly pestered us for chips and companionship. A few threatening looks and an intimidating motion to “scat” kept them at bay for most of the time we were there.

For our relaxing day by the water, I opted for the We The Free Lexi Poplin Button Down Shirt; it was the perfect throw-on-and-go layer. I then sported matching thrifted drawstring shorts to keep the outfit cohesive, and a simple baseball cap to keep the sun off my face.

A couple of chapters into my beach read, I decided to take a quick dip in the warm water of the Atlantic. The waves were lazy, and seaweed covered the water's edge, making getting in a slimy affair. I floated on my back, enjoying the rhythmic current that surrounded me and stared at the wispy clouds slowly drifting across the pale blue sky.

Eventually, we had to retreat; the sun, seagulls, and the chance at a real meal (not made of chips or soda) enticed us to leave. Fighting off the desperate stares of the birds, we took our spoils of war—half-eaten chips and cookies—with us.
Woman in white shirt and blue cap shielding eyes at beach, shown in two side-by-side photos with ocean and sand backdrop.

The rest of our adventure was a delightful blend of sipping rich coffee, hunting for treasures in thrift shops, and meandering through tourist traps, all in search of the perfect souvenirs for our friends and family.

As you celebrate Labor Day Weekend—whether it’s at a backyard barbecue, by the pool, or simply bidding farewell to warm weather—aim for a cohesive look featuring staple cotton pieces, relaxed denim, and a neutral color palette for effortless styling.

YOUR LABOR DAY LOOKS

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From The Desk Of: Sarah Elson

Sarah Elson is an Editorial Assistant who started her career at Free People just under a year ago. Despite being a relatively new member of the company, she has already accumulated over five years of experience in the fashion industry. Elson's love for fashion–and vintage–began in her youth when she first went shopping with her grandmother and mother. This passion, combined with her interest in writing, inspired her to pursue a career as a fashion journalist. She has interned with Future Snoops (formerly known as Fashion Snoops) and worked for notable publications such as WWD, Footwear News, Forbes, and The Business of Fashion.
Woman with curly red hair wearing white headband and black-and-white striped sweater with red lobster design by the ocean