Sentimental family elements made this large wedding feel intimate and unique.
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Matchmaking parents may be a romantic comedy staple, but for Chelsea Leonard and Conor Mara, they were a real thing. The New Yorkers met in 2013 while dining out with their respective parents, who happened to be neighbors in Palm Beach. Though they began dating a few months after that initial encounter, they credit their parents for setting their relationship in motion. Fast forward four years, when Conor popped the question with an Oscar Heyman ring after a bicycle ride to one of the couple's favorite Palm Beach spots—an inlet where they frequently went to feed bread crumbs to the fish.
On April 14, 2018, the couple and their 350 guests gathered at a private beach club (not too far from Conor's proposal location) for a wedding that was full of personal touches—from a cake inspired by the bride's grandmother's childhood nickname to the to custom New York Giants caps (a nod to Conor's grandfather, NFL legend Wellington Mara). "It was really big, but it didn't feel that way," says Chelsea. "Being surrounded by people who have always supported us, as individuals growing up and as a couple growing together, made us feel so loved."
Before the big day began, the weekend kicked off with a colorful, poolside welcome party, which—like the main event—was planned with help from Posh Parties. "Seeing everyone together, kicking off our wedding weekend, was really exhilarating," says Chelsea. "For us to have all our friends and family in one place, coming together to celebrate our love and marriage, was my favorite part."
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Chelsea knew exactly what she wanted for her wedding's stationery and signage—a personalized watercolor crest with calligraphy—but couldn't find an artist who's style matched her vision. Her mother's best friend, painter Melinda Trucks, surprised the couple with custom save-the-date artwork that set the tone for their future invitation suite and, ultimately, the wedding. "It was tropical and romantic, but most of all it was very sentimental," says Chelsea. "Our suite is one-of-a-kind and tailored just for us by someone who knows us very well and who we consider family." Third & Ivy designed the rest of the set, which included invites to the welcome party and thank-you notes. HeartSwell provided the calligraphy.
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About 230 guests traveled to Palm Beach ahead of the ceremony to take part in the couple's welcome party, which was hosted at the Sailfish Club of Florida. The duo chose a color palette of bright pink, yellow, orange, and green—inspired by the Italian coast!—and completed the décor with floating floral arrangements that drew the pool into the rest of the space.
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It wouldn't have been a Florida wedding without a touch of citrus. Oranges, clementines, and kumquats were woven into the welcome party's begonia centerpieces.
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The specialty cocktails honored both the bride and groom's mothers: They served a glass of Whispering Angel in honor of Chelsea's mother, and an Aperol spritz for Conor's. The third in the trio of offerings was an limoncello—an Italian classic.
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The Earth + Sugar groom's cake, designed by Conor's mother, Kathleen, featured alternating tiers of vanilla cake and vanilla buttercream with chocolate cake and chocolate buttercream. Bougainvillea and sugar lemons added cheerful color. The edible football was a nod to Conor's family, who has a long-time connection to the New York Giants.
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Guests were treated to Palm Beach-themed welcome bags that included saltwater taffy, orange mints, Old Florida Gourmet Products tortilla chips, fresh clementines and apples (the fruits represented the couple's roots in Florida and New York), and baseball caps with "CC" and the wedding date embroidered on the side.
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Meant to Be
Chelsea tried on plenty of wedding dresses in New York without finding the one, but fate intervened on a trip to Ever After in Miami with her mother. Hurricane Irma had delayed an Oscar de la Renta trunk show until the day of Chelsea's appointment, which is when she found her strapless guipure lace gown. "I was so lucky!" Chelsea says. "I never thought I would have a wedding dress with a big bow in the back, but Oscar really did it right. The bodice was so flattering, from the high pointed neckline to the cinched waist, and I was in love from the first second I tried it on." She chose timeless jewelry that was a mix of old, new, and borrowed: Van Cleef & Arpels earrings on loan from Conor's mother, a diamond tennis bracelet Chelsea's father gave her mother on her first Mother's Day, and a Tiffany & Co. diamond band that was a gift to Chelsea from her father.
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Getting the Blues
Three of Chelsea's closest childhood and high school friends served as her bridesmaids. The group wore mismatched navy dresses from Monique Lhuillier and carried bouquets of white ranunculus, garden roses, peonies, and lily of the valley. The couple also included all of the children in Conor's family in their ceremony. As flower girls, his two nieces wore ivory tea-length Oscar de la Renta dresses (just like the bride!).
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What's in the Box?
Conor opened his wedding gift from Chelsea—a Rolex watch—as his nephew Blaise, one of the ring bearers, watched. "We gave the little boys shark tooth necklaces the morning of the wedding," says Chelsea. "Blaise especially is obsessed with sharks so he probably thought there was going to be some cool shark thing in that box."
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Conor and his three groomsmen—his brother, his cousin, and a friend—wore black tuxedos. "Chelsea took on a lot of the wedding planning responsibility so I didn't let her have a say in my tuxedo or my groomsmen's," says Conor. His custom Élevée tuxedo was lined with blue fabric; he chose black leather-and-tweed loafers from Gucci with a bee on the heels to honor his bride's love for the insects. Though Conor wore a black bow tie, his groomsmen (in looks from The Tux Shop) and nephews sported ties and pocket squares in colorful Liberty of London prints—another favorite design of the bride's.
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Going to the Chapel
The couple decided not to have a first look since Conor wanted to follow the tradition of waiting to see Chelsea for the first time during the ceremony. The bride's father escorted her down the aisle at Royal Poinciana Chapel to Wagner's Bridal Chorus—a choice Chelsea made well in advance of the ceremony. "This is such a classic wedding song and I frequently caught myself humming it during our year-long engagement," she says. "It felt like a rite of passage walking down the aisle on my dad's arm to that song."
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Faith and Family
The Royal Poinciana Chapel is a non-denominational church, but Chelsea and Conor wanted to incorporate both their family's faiths into the ceremony: They had two officiants, a reverend and a priest, to honor her Episcopalian background and his Catholic one. Conor's cousin, Molly, and his brother-in-law, actor Jamie Bell, each read a selection from the Bible.
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After the ceremony, the newlyweds climbed into a vintage Rolls Royce and decamped to Conor's grandparents' home for photos. His parents had organized the hanging of a "Just Married" banner and a collection of New York Giants footballs on the rear bumper. "My grandpa Wellington Mara's nickname, "The Duke," is on every NFL ball ever made," says Conor. "It was special for that to be a part of our wedding."
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Leaves and Love
At Conor's grandparents' home in Palm Beach, a hand-painted mural of leaves and plants on the open-air loggia created a stunning backdrop—but Conor and Chelsea weren't the first to take advantage of the artistic scenery. "Slim Aarons actually used their loggia for a photoshoot a long time ago, so we kind of took that idea from him," Conor says of taking their cue from the famous shutterbug.
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Mom (and Dad) Know Best
The mother of the bride wore an embroidered floral gown by Temperley London, while Conor's mom chose a white Dolce & Gabbana dress with red floral accents. Since both sets of parents have been married for more than three decades each, they had plenty of wisdom to share with the newlyweds. "The marriage advice my parents gave us was to never go to bed angry at each other," says Chelsea. "Each new day is a chance to do better. Conor's parents said compromise and lots of laughter are the keys to a long marriage."
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The couple used the same crest that appeared on their stationery suite to create a 3D monogram, which was backed by blue and white faux flowers, to hang over the fireplace They loved the end result so much they plan to have it framed for their home.
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Tables were set with a mixture of high, medium, and low vases filled with combinations of blue and white hydrangeas, roses, peonies, sweet peas, ranunculus, tulips, lilacs, and cherry branches. "When I asked Conor what type of flowers he envisioned, he chose the blue hydrangeas, which he knew were very special to me too as a reminder of my childhood in Bridgehampton," says Chelsea. "We love blue but it's easy to go overboard with blue. I knew I wanted something classic and timeless, something I could look back at and still think was beautiful."
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A Family Affair
Conor's sister, actress Kate Mara, and her husband, Jamie Bell, were among the guests who celebrated with couple during dinner and dancing at a private club in Palm Beach.
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Menus and Matchmakers
Subtle blue-and-white china with silver flatware incorporated the couple's color palette, while a vibrant orange kumquat was a callout to the street both families own homes on in Palm Beach. Each place setting included a menu with watercolor art from family friend Melinda Trucks and dinner options penned by HeartSwell; the menu also acted as a place card, with names added at the top by calligrapher Stacey Podell. "I loved that personal touch," says Chelsea. "It made it clear that we took the time to think about each guest and where they would have the most fun! Based off people's stories and how many couples got together at our wedding and are now dating, it seems like we did a good job with the seating assignments!"
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But First, "At Last"
Conor and Chelsea chose Etta James' timeless version of "At Last" for their first dance—after some trial and error at home. "We danced to a lot of songs alone in our living room to figure out what our first song should be," Chelsea says. "This one was so obviously for us. I'll never forget the first time we danced to it together during the coldest day of winter."
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The five-tier semi-naked lemon-and-blueberry cake from Earth + Sugar was decorated with fresh berries and grapes as a subtle nod to Chelsea's late grandmother. "Blueberry was her nickname for me and she adored Conor, so I wanted to include her in a big way in our day," she says.
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Chelsea's habit of collecting Herend figurines made them an easy choice for the cake topper. "I have had my eye on the bride and groom penguin for some time now!" she says. "I knew they were perfect for the top of our wedding cake, and that blue color was meant for us."
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In the Books
Guests signed a coffee table book, which the couple plans to read through on their first anniversary while enjoying a piece of the wedding cake tier they saved.
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On the Dance Floor
The band, The Sultans, "knocked it out of the park," choosing a playlist of songs from more than 100 that the bride and groom suggested. "The music and dancing were really important to us," says Chelsea. "We picked the band before we even picked a wedding date!" The evening was filled with dance-offs, push-up contests, sing-offs with the band, and even a rap battle with the DJ. "I think that's when the police arrived to shut us down," said Chelsea. "Needless to say, we all had the best time and no one wanted the party to end."
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Sweets to Go
Take-out boxes were stationed next to a buffet of candy and treats, allowing guests to grab a few sweets to go. The selection included several of the couple's favorites: watermelon Jolly Ranchers, Twizzlers, Reese's peanut butter cups, sour straws, M&Ms, and cookies.
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Photography, KT Merry
Event planning, Posh Parties
Videography, Senderey Video Productions
Calligraphy, HeartSwell; Stacey Podell Calligraphy
Cake, Earth + Sugar
Music, The Sultans
Bride's gown and veil and flower girl dresses, Oscar de la Renta
Hair, Tiffnie Robertson
Makeup, Jane Pittman
Bridesmaids' dresses, Monique Lhuillier
Groom's suit, Élevée
Groom's shoes, Gucci
Menswear, The Tux Shop
Groomsmen's bow ties, Liberty of London
Ceremony Location, Royal Poinciana Chapel
Rehearsal dinner location and catering, Sailfish Club
Rehearsal dinner décor, Renny & Reed
Rehearsal dinner guitar and vocals, Joey Calderaio