Oscar de la Renta + Pajamas Chicago Winter Wedding

When a bride can go from a gorgeous Oscar de la Renta wedding dress to pajamas before the ceremony, it’s not your average Chicago winter wedding! Courtney + Jake made their Chicago winter wedding truly unique and perfect for them.  

That Courtney + Jake are a perfect match was obvious to me the first time I met with them to talk about their wedding. Almost immediately they started bantering back and forth about everything from what they were going to have for dinner to hockey. I was pretty sure they forgot I was sitting with them, but I didn’t care because it was so cute to see two people so crazy about each other.

“As a Dad, whenever your daughter tells you there’s a guy, you immediately want to know if it’s that guy.  She says, there’s a guy at work who likes me. Which I immediately know that means there’s a guy at work that she likes.”

From her gorgeous Oscar de La Renta dress paired with pink Chuck Taylor’s and leather jacket to her pajamas she sported for the Ketubah signing, Courtney created her own wedding style. Courtney also made sure her bridesmaids were styling. She had custom leather jackets made for all of her bridesmaids. Not to be outdone, Jake bought Chuck Taylor’s for all of his groomsmen, including Courtney’s Dad.

While Courtney + Jake are on opposite ends of sporting rivalries, they share a sarcastic sense of humor and love to make each other laugh. Courtney wanted to punk her hubby-to-be. With the help of her brother, she bought Jake a cheap Casio watch as her gift to him that he would open in front of his groomsmen. Ever the gentleman, however, Jake hid his real reaction to the gift and pretended to be excited by it. Much to his relief, Courtney had actually bought Jake custom high tops complete with their wedding date imprinted on them. 

Jake decided to go for sentiment and not humor when he gave his beautiful bride a treasured gift from Tiffany. Wise move, Jake!

Both Jake and Courtney made sure that their families were an important part of their celebration. Courtney brought her tough lawyer Dad to tears when she showed him that she had her grandparents names stitched onto her veil. 

Surrounded by their big fun families, the whole day was filled with so much love and laughter. Even the Rabbi cracked a few jokes during the ceremony. Mazel tov Courtney + Jake!

Venue: Temple Shalom
Hotel: Hotel Monaco
Dress: Oscar de la Renta
Hair/Makeup: Rare Bird Beauties


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