Kendra and Brett’s fall wedding at The Blackstone Hotel brought Gatsby glamour to the heart of downtown Chicago. Set inside a historic ballroom filled with crystal chandeliers, deep-hued florals, and candlelight, their celebration mixed elegance with personality — from a saxophone serenade to a secret handshake and late-night Taco Bell.
Location: Chicago, Illinois, USA
Style: Glam, elegant, old-money
Time of planning: 19 months
Number of guests: 130
Setting: Ballroom
Season: Fall
Brett and Kendra met during a summer in Kenosha, Wisconsin, when a mutual friend set them up on a blind date at Applebee’s. What started with shared sweet potato fries turned into a summer of baseball games, driveway chats, and late-night FaceTime calls once the season ended. Despite years of long distance through nursing school and law school, they stayed connected. Brett eventually pulled off a 30-hour surprise trip to Ireland, showing up at Charles Fort where he proposed just as Kendra reached the top of a hike. Her shocked “Yes!” was followed by a Guinness toast with friends and family at a local pub.
Bridal Morning
Kendra started her morning surrounded by her bridesmaids, sister, and mom in a suite at the hotel. The space buzzed with excitement as Dani from Dani Garcia Brides styled her hair into a loose high French twist with soft layers framing her face — a look Brett had always loved on her. For makeup, she kept it soft and natural with subtle pink hues on her eyes, inspired by the rehearsal dinner look her friend Molly created the night before. Kendra wanted to feel like herself, just elevated, and the finished glam reflected exactly that.
Her accessories were deeply personal: her mother’s pearl earrings, a sapphire ring gifted by her sister — her “something blue” and birthstone — and a simple cathedral-length tulle veil.
Her dress, by Eisen Stein from Jenny Yoo NYC, featured long sleeves, an open back, a deep V neckline, and intricate sheer detailing — a design she hadn’t expected to fall for, but instantly knew was the one. “It felt incredible,” she said. “It was sexy, detailed, open back, long sleeved, deep-V neckline, and nothing I had ever seen before.” She paired it with simple, comfortable shoes perfect for dancing and skipped the idea of a second dress entirely. “I wanted one dress for the one big day!” Everything about Kendra’s look felt intentional — refined, romantic, and true to herself.
"I love the drama that comes with a cathedral veil, so that was a must."
Groom's Fashion
Brett chose a classic black-tie look with a sharp Vera Wang tuxedo, bow tie, and suspenders — a subtle nod to his game-day travel outfits from baseball season. He skipped the vest for a cleaner silhouette and finished the look with a boutonniere of maroon and pomegranate tones with greenery. “He looked incredibly handsome — very different from his Sunday Best: his favorite sweats and hoodie,” Kendra joked.
First Look
Brett and Kendra shared their first look just outside The Blackstone Hotel, surrounded by golden fall trees and the quiet buzz of downtown Chicago. The second Brett turned and saw Kendra in her dress, nerves melted away. “Before the first look, I thought back to how I had calmed my nerves in similar situations,” Brett shared. “Once I made eye contact with my catcher, everything else—the crowd, the players, the pressure—would fade into a bright, white blur. I used this technique the moment Kendra met me at the altar.”
Their hight five came right after — instinctive and perfectly in sync. “They would do so in such a way that it would happen simultaneously — literally an instinct they both had at the exact same time,” said photographer Sam of Everly Collective.
"Yes, they are the total package, unreal."
Ceremony
The ceremony took place in the historic ballroom, where ornate white walls, grand mirrors, and gilded sconces set the scene for a glamorous celebration. A white aisle runner led guests through the room, flanked by glass pillars filled with mauve hydrangeas, rust-toned dahlias, and dried textures arranged by House Finch Floral. Candles of varying heights flickered between seasonal fruits — figs, persimmons, and pomegranates — creating a warm, romantic glow. Petals were scattered at the base of each arrangement, enhancing the layered look of the florals. With its mix of fall tones and Renaissance-inspired elements, the setting felt rich, artistic, and true to the couple’s vision.
"We wanted our ceremony to be short, sweet, and embody the same amount of humor shared in our relationship."
Guests were welcomed with champagne and greeted by the flash of Sam’s camera, giving the arrival a red-carpet feel. Kendra walked down the aisle with her father toward Brett, who had helped write a ceremony that was short, personal, and filled with humor. Kendra’s honorary uncle Kevin delivered an Irish blessing with theatrical flair, honoring her heritage and their engagement in Ireland.
Brett’s Jewish tradition was marked by the breaking of the glass — heavily bubble-wrapped, thanks to his father’s precaution. “To this day, we are uncertain if the glass actually broke,” Kendra joked. As they sealed their vows with a kiss, “Radio” by Lana Del Rey played, and again in perfect sync, they high-fived.
Private Moment
After the ceremony, Brett and Kendra stepped away for a private moment inside the hotel sharing a quiet pause before rejoining their guests. Tucked into one of the hotel’s richly detailed spaces, the atmosphere shifted from celebration to stillness. Their photographer, Everly Collective, captured this intimate time with a calm, unobtrusive presence, focusing on their connection and the quiet joy between them. The result was a series of portraits that felt deeply personal — reflective, romantic, and full of calm emotion.
"The photos are only as good as the energy and emotions you bring. My job isn’t to make your day look a certain way. It’s to preserve and honor it just how it felt, in an artful way. I fed off of life provided on Kendra and Brett’s day and truly felt connected to each moment."
Decor & Setting
The reception carried the same romantic opulence as the ceremony, held in the grand ballroom. Long tables were dressed in cream linens and topped with layered fall florals, featuring mauve hydrangeas, dusty pink roses, and seasonal greenery. Scattered among the arrangements were figs, persimmons, grapes, and pomegranates, giving the tables a Renaissance-inspired look. Dozens of candles in varied glass holders added a warm, flickering glow to the room, while fruits and petals softened the structured elegance of the space. The combination of deep tones, natural textures, and old-world styling brought Kendra’s vision of “Gatsby romance meets French elegance” to life.
"We wanted deep colors of mauve, navy, and reds. Kendra absolutely loves hydrangeas. They remind her of her father’s garden-–blooming with large bushes of flowers every summer."
Reception
As guests took their seats, the dinner began with heartfelt toasts and the sound of soft jazz echoing through the ballroom. Kendra and Brett’s signature cocktails reflected their favorite memories — a Hugo Spritz inspired by her bachelorette trip to Tuscany, and Brett’s legendary dirty martini, complete with blue cheese olives.
The cake, created by Bittersweet Pastry Shop, was minimal and classic with a touch of fall detailing — designed to complement the rest of the decor. Positioned on a table surrounded by flickering candles and scattered petals, it looked like a still-life painting. When it came time to cut the cake, Brett and Kendra stayed true to their playful energy. Their synchronized high five followed the first slice, keeping the tone light and joyful.
After dinner, they took to the floor for their first dance to “Forever” by Lee Fields. “What started off as a Super Bowl commercial song about puppies soon became a front-runner for our first dance,” Kendra said. The song’s soulful rhythm matched the mood perfectly, ending with another instinctive high-five as the crowd erupted around them.
Night
As the evening carried on, the dance floor filled quickly with music that jumped from Leon Bridges to Creed. The live saxophone performance by Chicago Street Strings during cocktail hour had already set the vibe, and the energy only grew from there. The final touch? A massive Taco Bell order to cap off the night, enjoyed in bed while debriefing the day. It was the perfect mix of glamor and real life — entirely them.
“It’s not about the journey, and it’s not about the destination –it’s about the company, which is why it was so important to have everyone we love in one place, at one time.
Advice from the couple:
• Let’s be real, it’s hard to plan a wedding. You become consumed by Pinterest, influencers on Instagram, and the opinions of others. There’s a new trend every month–it’s impossible to keep up! My key advice would be to go with your gut and make decisions for the two of you. The day is about YOU.
• Don’t stress and go with the flow the day of–be present! Everything will work out. At the end of the day, all that mattered was that I got to marry my best friend.
PHOTOGRAPHER Everly Collective | VIDEOGRAPHER Film & Fable Co. | VENUE The Blackstone Hotel | FLORIST House Finch Floral | MUAH Dani Garcia Brides | STATIONERY Maria Gossard Designs | DRESS Eisen Stein via Jenny Yoo NYC | SUIT Vera Wang | CAKE Bittersweet Pastry Shop | DJ Green Line Talent | STRINGS & SAXOPHONE Chicago Street Strings
