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A Twist on the Traditional: Emily Rennert and Simon Wein Wed in an Intimate Courtyard Ceremony at Swan

By Shayna Seid | Photography by 

Lucy Cuneo & Joseph Rogero

|Planning by 

Orange + Rose Events

After sharing a house with mutual friends in Fire Island one summer, Emily Rennert and Simon Wein kept running into each other back in the city. However, it wasn’t until spring, when they went on their first date to The NoMad Hotel bar.

The two had been together for a little more than four years, when Simon surprised Emily with a proposal at home. She had been anticipating a proposal for months, but on May 1, 2021, she assumed there was no way he would propose on a weekend when she had to work. Simon told her he had an early tee time that morning, but he really went to the flower district with his best friend and Emily’s sister to set up the proposal. When Emily came home from her Saturday SLT class, she found her boyfriend down on one knee surrounded by pink and white roses with “Beyond” by Leon Bridges playing in the background.

As Emily had grown up in Miami, she felt like she had been to so many of the same type of wedding and was opposed to looking in the city. However, Simon loves her hometown, and she jokes that he’s the real Mr. 305 in their family, even though he’s a New Yorker. It was actually Emily’s mom who suggested their host their celebration at Swan, Pharrell and Dave Grutman’s restaurant. The venue had never hosted a wedding before, but once the bride-to-be saw the location, she was sold. The interiors reminded her of Miami in the ’20s, and the upstairs space was perfect for a party. To help plan everything and bring their vision to life, the couple hired Liz Ryan and Lizzie Eisenberg of Orange + Rose Events.

Before the venue was booked, Emily started looking for her wedding dress. “I really thought I wanted something non-traditional and was eyeing a high-low type of dress,” she notes. Shanice at Vera Wang expertly pulled the Ceres gown, which was originally from the Fall 2019 collection and incorporated into the bridal offering in 2020. Once Swan was confirmed, Emily went back to the showroom to try it on again and knew she had found “the dress.” “We were getting married at a venue where no one else had ever been married, and the dress had never really been worn by any other bride—just on a red carpet—it felt perfect,” Emily gushes.

On the day-of, Emily got ready with makeup artist Camille Thompson and hairstylist Marc Mena, who perfected her bridal beauty look. “Marc and I loosely used Hailey Bieber’s wedding hair as his inspiration but with a bit of a modern twist and more defined pieces to make it more me,” Emily explains.

To complete her bridal ensemble, Emily’s friend and stylist Sarah Slutsky helped the bride get a hold of the Jimmy Choo Sacora 100 heels, and Emily’s mother and grandmother lent her their diamond stud earrings and eternity band. The icing on the cake was getting to wear Emily’s mother’s wedding veil, which Emily’s sister, Jenna, also wore two years prior.

On December 19, 2021, Emily and Simon were married in the courtyard under a chuppah crafted from two trees and Emily’s grandfather’s tallis. The bride walked down the aisle with her parents to traditional Hebrew love song “Erev Shel Shoshanim,” which her mother also used as the processional tune at her wedding. “The week prior, the rabbi has asked each of us to independently email him a few sentences about what we admire about each other,” the bride explains. “Hearing that for the first time during the ceremony was a really special moment that I don’t think either of us thought we would appreciate as much as we did.”

“I am not one to love attention and was afraid that we would both be nervous standing under the chuppah with so many eyeballs on us, but I really felt the opposite,” Emily says. When the rabbi wrapped the couple in Simon’s tallis, it especially felt like the world was standing still.

Once the two were announced as husband and wife, the cocktail hour began in the Art Deco-influenced dining room. Then everyone moved back outside for the seated dinner at long rectangular tables. “The courtyard was transformed into an ethereal evening thanks to Veronica at Anthology Floristry, who completely understood my vision and was able to bring it to life,” Emily says.

The meal was served French-style, starting with two salads, followed by a pasta course, a choice of branzino, wagyu rib-eye, or cauliflower steak, and family-style sides. From the beginning, the couple never wanted to serve a wedding cake but opted for a minimal two-tiered white buttercream cake, from Earth and Sugar, to cut—truthfully, just to have for their anniversary.

To get the party started, the Bop Shop Brass band led everyone up the stairs, where they were greeted by an entire room filled with the new mister and missus’s favorite baked sweets, a candy bar, and DJ Mayner.

For the festivities, Emily changed into a Retrofete white and silver sparkle mini dress with high-top white Nikes. “I really wanted to be able to just dance!” she exclaims. Upstairs, late-night bites and cortadito shots kept the energy up until the early hours. And outside, Tight Ashes rolled Cuban cigars with custom “Emily & Simon” wrappers and matchbooks.

As guests left as late as 3:00 a.m., they were tempted by a Churro World Co. food truck serving warm churros with chocolate and dulce de leche dips—a last farewell from the newlyweds with a major sweet tooth.