As a Chicago wedding planner, one of the true joys of my job is getting to know the families I work with throughout the planning process. The bittersweet part is that, at the end of a wedding day, I rarely get a “repeat” client.
That is why I have intentionally shifted my client roster toward working with legacy families, along with their friends and colleagues. It creates such a wonderful rapport from the very beginning. And really, aren’t referrals the ultimate compliment to your skills?
I was lucky enough to plan three family weddings in less than 18 months for this wonderful family. Each sibling had a celebration that was classic and timeless, yet completely unique to them. Clare and Brian’s wedding was the third celebration in this incredible family three-peat.
A Chicago Wedding Three-Peat
Because this was our third wedding with the family, we already had a few vendors who were complete non-negotiables!
Olivia Leigh Weddings had captured the family so beautifully at their previous celebrations. For Clare and Brian, she once again brought her signature romantic, timeless, and intimate photography style to the day.
HMR Designs also returned, creating another beautiful green-and-white design. However, they approached the look in a completely different way, making sure this wedding felt distinctly Clare and Brian’s.
And, of course, the magicians at Steracle Press were back to add those small, thoughtful details throughout the stationery. From the paper goods to the guest-specific touches, the details made the celebration feel personal from the moment guests arrived.
A Traditional Catholic Ceremony in Chicago
Clare and Brian began their wedding day with a traditional Catholic ceremony at Old St. Patrick’s Church. From there, guests headed to The Chicago Club for a formal black-tie wedding reception.
Rain was not part of the plan, but a quick shower as guests departed the church ended up creating some of the most memorable candid photographs of the day. Guests gathered under striped umbrellas, creating a fun and unexpected moment for Olivia Leigh to capture.
Most importantly, the rain perfectly reflected Clare and Brian’s laid-back personalities. They could not have cared less about a few raindrops, and that relaxed attitude made the photographs even more authentic.
A Classic Green and White Wedding Reception
At The Chicago Club, we dressed the dinner tables in crisp white textured linens with pops of summery green. Custom topiaries, soaring palms, fresh fruit, and delicate maidenhair fern came together to create lush centerpieces with a classic, garden-inspired feel.
The place settings were finished with oversized menu cards customized for each guest. It was a simple detail, but one that made the formal reception feel personal and welcoming.
Then came the cake.
The soaring, tiered wedding cake by ECBG Cake Studio was every bit as delicious as it was gorgeous. Clare’s expression while cutting and tasting the cake says it all—and Olivia Leigh captured the moment perfectly in a single frame.
Dancing, Dessert & Ravioli
Once dinner and dessert began, the celebration turned into an epic party with the Gold Coast All Stars. The dance floor was packed, giving guests the perfect opportunity to celebrate Clare and Brian well into the evening.
For the perfect take-home treat, guests received custom cookies from The Cookie Room. The inspiration? The bride and groom’s beloved dog, Ravioli.
Of course, Ravioli could not miss out on the celebration entirely. He made an epic cameo in the custom cookie designs, giving guests a fun and personal reminder of the couple to take home.
A Wedding That Was Completely Their Own
From the traditional Catholic ceremony to the black-tie reception at The Chicago Club, every part of Clare and Brian’s wedding felt classic, elegant, and personal.
The unexpected rain, lush green-and-white florals, customized stationery, beautiful cake, incredible music, and Ravioli-inspired cookies all came together to create a celebration that reflected the couple perfectly.
Planning three weddings for one family in less than 18 months was an incredible honor. Getting to know each sibling and helping each of them create a wedding that felt uniquely their own was even more special.
It is one of the reasons I love being a Chicago wedding planner. The relationships that begin during the planning process often become the most meaningful part of the celebration—and there is nothing quite like being invited back to celebrate with a family again and again.
Vendor Team
- LOLA Event Productions: Lavish LOLA Planning Package
- Photography: Olivia Leigh Weddings
- Glam Squad: Livia Caporale Hair Shannon O’Brien Bridal
- Décor: HMR Designs, Frost Chicago, BBJ Linen, Halls Rental
- Cake: ECBG Cake Studio
- Transportation: Premier Trolley
- Stationery: Steracle Press
- Bride Prep: The LaSalle Chicago
- Gown: Ultimate Bride, Monique Lhuillier
- Favors: The Cookie Room
- Entertainment: Gold Coast All Stars
