The Secrets and Bonds Hidden in The Dress Codes Of 'The Five-Star Weekend’

In “The Five-Star Weekend,” of course, perfectionist food influencer Hollis (Jennifer Garner) would compose a structured, if not rigid itinerary for a Nantucket girls retreat that includes a strict Instagram-worthy dress code. 

Grappling with grief after the tragic death of her surgeon husband Matthew (Josh Hamilton), Hollis gathers four close friends at her sprawling compound on the picturesque New England island. She brings them all together through coveted reservations at an exclusive restaurant, immaculately presented drinks and meals, and very specific color palette guidelines. “If somebody issued dress codes to something I was invited to, I'd be like, ‘No, lady,’” says costume designer Susie DeSanto, with a laugh. “But it made for fun costuming moments and provided a challenge because they came from different periods of Hollis's lives.”

The Perfect Host

At the behest of her publicist Chelsea (Vella Lovell), Hollis also agrees to capture #content of the aspirational weekend. So she welcomes her guests—and runs into her hometown ex, Jack (Timothy Olyphant)—in a pastel blue-and-white gingham sundress by Jonathan Simkhai. 

To inform Hollis’ picture-perfect wardrobe (filled with Sézane, Jenni Kayne, Ralph Lauren, and Goop,) DeSanto looked to social media-famous culinary figures: chefs and authors Ina Garten and Alison Roman, plus Londoner Ella Mills and Los Angeles-based private chef Eleanore Toulin for a Parisian touch. “Visually, [Toulin] was a real inspiration and I took that to Jen,” says DeSanto, who has regularly collaborated with Garner since the 2004 rom-com, “13 Going on 30.” “I landed on Hollis’ blue-and-white color scheme—that’s very prevalent in Nantucket—and I needed it to have that East Coast vibe.”

But of course, Hollis' ultra put-together wardrobe—paired with a sublime galette packed with farmers market-fresh blackberries and a meticulously arranged cheese board—telegraphs something deeper. “Hollis, at this point in her life, is trying so hard to keep it together,” says DeSanto. “These are all issues of control. It's trying to organize what you can organize because you can't organize the emotional turmoil and the grief.”

The Arrival of Old Friends

Since Matthew's funeral and her daughter Caroline's (Harlow Jane) return to college, Hollis has withdrawn from both work and the people who care about her. She hasn't returned calls from her closest friends: college bestie Dru-Ann (Regina Hall), now a sports agent in Los Angeles; childhood friend Tatum (Chloë Sevigny), who's running her family’s dry-cleaning business on Nantucket; and Brooke (D'Arcy Carden), a fellow mom from affluent, academic Wellesley, Massachusetts, who rushed to the hospital after Matthew's accident. They’ve all packed in compliance with Hollis’ exquisitely printed invitations and dress codes.

“Dru-Ann has a super high power job in that sports world. She dresses in really expensive clothes,” says DeSanto, who shopped brands like Versace, Fendi, Gucci, Celine, Isabella Marant, and Gabriela Hearst. Dru-Ann’s vibrant red-and-white swirl mini-shirt dress by Alexis seamlessly transitions from seated dinner to pajama dance party by the pool. “She always wears heels,” adds DeSanto. Tatum, who has clashed with Dru-Ann since Hollis’ wedding, notes and scoffs at the Los Angeleno power player’s impractical Saint Laurent shoes.

“Tatum is so authentically the island,” says DeSanto, who faced the challenge of playing down Sevigny's famously eclectic fashion sensibilities. “But Chloë also really knows that local, East Coast, small-town person. So we approached it as Tatum has style and things, but she doesn't want to spend money on it. She's the complete polar opposite of Dru-Ann.” Although Tatum bristles at the idea of a dress code, she ultimately indulges her old friend, dressing for dinner in a sweet, vintage-inspired puff-sleeve Reformation dress.

“Then there's Brooke, who's just struggling to fit in,” says DeSanto, who looked to actual Wellesley moms groups to craft Brooke's upscale, but overly floral aesthetic. She awkwardly attempts selfies on the ferry in a very pink Oscar de la Renta dress-and-cardigan set, topped with a floppy straw hat made for Carden’s deft physical comedy. Brooke changes into a similarly floral, but more prim Oscar de la Renta halter dress for dinner. “We really use that as a template for somebody who's massively insecure and trying so hard to fit into the group of women that she runs with,” says DeSanto.

The Wild Card

To complete the “five stars” theme of the weekend, Hollis invites Gigi (Gemma Chan), a new friend she met in the Instagram DMs while estranged from her old friends. They remain skeptical about the newcomer—especially after Hollis admits she hasn’t gleaned much from a Google search. “She’s a ghost,” says Brooke, as Gigi glides into the kitchen mid-dinner in an elegant all-white linen set: LaPointe trousers and an ALC vest.

“The word I always use to describe Gigi is ‘enigmatic,’” says DeSanto. “Gigi kind of floats into the world in that white column. I didn't want a lot of color on her. I wanted her comfort zone to be a serene, limited palette.” DeSanto saved the bulk of The Row pieces for Gigi, along with minimalist quiet-luxury brands, like Bruno Cucinelli, MaxMara, Nili Lotan, and Chloé. Gigi, who claims she lost her mother, connects with Hollis over their collective grief—and their shared need to find control through their wardrobes.

“Like Hollis, she's also trying to organize her life and her things so it's manageable for her,” says DeSanto of the teetotaling Delta pilot. “Like she says, ‘I don't drink that much because I want to stay present and clear.’ So she's another character who is really trying to keep things under control and maintain the chaos. I just wanted everything to be super simple, with clean lines and really beautiful.”

Orange & Pink Overload

For a scheduled Saturday with shopping in quaint downtown Nantucket and relaxing spa treatments, Hollis envisions a pink-and-orange theme—which pushes Tatum’s limits, but she reluctantly throws a lace-trimmed slip dress, by J. Crew, into her weekender. “Dru-Ann just rocks a Totem outfit,” says DeSanto, imagining that the sports agent effortlessly plucked a chic burnt-orange printed set from her extensive closet, while Gigi presumably resurrected a ruched Matteau sundress, in an uncharacteristically dusty coral-pink, from a past jaunt to the Maldives. “Brooke probably overthought [her cap-sleeve Caslon dress] forever and ever, and got a print that was a little bit too wild.”

But no one curated their Nantucket wardrobe quite like Hollis. She had clearly preplanned every outfit for the weekend, especially her sorbet-hued tropical-print Monique Lhuillier dress. DeSanto actually bought it in Beverly Hills, thinking the piece perfectly captured the Nantucket vibe—only to spot the exact same linen style in a local boutique while filming. “Hollis had planned that really specifically,” says a proud DeSanto. “It was ready to go.”

The Dress Code Rebellion

Inevitably, as the weekend unfolds, longtime resentments and secrets emerge within the group. Feeling betrayed by Hollis, Brooke rebels with an outfit she purchased during an earlier shopping excursion with Gigi. While everyone else adheres to the black-and-white dress code for dinner at Nantucket hotspot, CRU, Brooke makes her grand entrance in a draped acid-green halter top and body-skimming black Ralph Lauren Purple Label jeans.

DeSanto explains that creator Bekah Brunstetter “loved the word ‘chartreuse,’” which was written into the group’s banter. So DeSanto dyed the customized top to bring that scripted detail to life—and help Brooke find a newfound confidence during ’80s night at the local dive bar. “We just wanted a completely different silhouette from the floral fit-and-flare to be a real breakout for her,” says DeSanto. “When [D'Arcy Carden] put those pants on, it was like, ‘We gotta go show the director.’ She was so excited. When you're doing fittings with actors and they find something that all of a sudden gives them what they need to do the scene, it’s my favorite thing. Those pants really rocked her life.”

Revealed Secrets and Relaxed Outfits

As revelations come to light and alliances form, the facades fall—even the sartorial ones. The women shed their carefully curated looks and relax into easy shirts, cozy sweaters, and, in Dru-Ann’s case, a bold, color-blocked shorts-and-shirt set paired with Chloé sneakers, instead of heels. “That Fendi outfit is one of the first things that I bought for Dru-Ann,” says DeSanto, imagining she’d consider it a “cute vacation piece.” 

To avoid tipping off a distressed Hollis, who’s resting inside the house, the four guests pretend to enjoy a friendly game of tennis. For the ruse, Tatum unleashes a pretty impressive backhand in a yellow-striped Charvet men's shirt with white J.Crew shorts. Brooke stands tall in a pastel-blue Reiss knit halter with wide-leg Max Mara trousers, while Gigi conveys vulnerability in an airy parachute shirt and cargo pants set by MeiMeij.

“At that point, it was more about dropping the pretense,” says DeSanto, who observed many groups of women in Nantucket wearing coordinating looks for the 'gram—much like the dress-code-observing friends earlier in the weekend. “Now it's just more about actually being who you are and being a real person—and talking about feelings rather than taking a picture of each other.”