An Elevated + Whimsical Fall Wedding in Chicago

“At the start of planning, we chose three words to guide every decision,” remember Bree + Jake of the approach they took when dreaming up their Chicago wedding day. Those three magic words? Whimsical, approachable, and elevated. “These words became our north star and ensured that every decor choice, menu item, and playlist addition felt authentic to us.”

The couple met doing improv in Chicago’s vibrant comedy scene. “Our shared love of laughter, creativity, and storytelling has been the foundation of their relationship ever since,” they say. 

When wedding bells started ringing for Bree + Jake, the funny pair collaborated with Lo-Fi Events and transformed The Joinery, an intimate yet industrial venue in Chicago’s Logan Square neighborhood (an area the bride + groom love) for their Big Day. With tons of customized details and a meaningful-yet-playful approach, Bree + Jake created a wedding aesthetic that centered their own love story. “Our goal was to create a wedding that screamed ‘Jake and Bree,’” says the couple, “a reflection of our personalities, relationship, and shared love of whimsy and fun.”

There color palette captured Fall romance with lots of earthy pastels. There were plenty of clever DIY projects. There was a Grand Exit in a vintage Mini Cooper. Thank goodness Allie Idrac was there behind the camera capturing everything so beautifully, because we can’t wait to share Bree + Jake’s heart-filled day with you!

One of our fave DIY projects from Bree + Jake’s day? These gorgeous minimal wedding invites! “Bree took a letterpress course to design and hand-print all the stationery, including invitations, programs, and menus, with design collaboration from Jake,” the couple says.

How precious are these custom embroidered vow books! What an incredible keepsake.

Bree’s unique, geometric blue stone engagement ring came from Mineralogy.

We love to see a mother of the bride dress with some serious sparkle!! ✨

The Moments Before

Bree’s gorgeous lace + satin bridal look from Unbridaled combined pieces from Alexandra Grecco and Jenny Yoo.

Pastel colors aren’t just for Spring, and this earthy, romantic bridal bouquet by Studio Poppy is proof! The muted, warm colors with pops of blue were perfect for Bree + Jake’s September wedding date.

Jake looked sharp + wedding ready in his Indochino wedding suit!

Love that Bree’s bridesmaids were all rocking bridesmaid dresses that matched one of the colors in Bree’s bouquet!

Also: monochromatic bridesmaid bouquets that correspond to dress color? Such a genius wedding flower trend.

The groomsmen’s boutonnieres corresponded to colors in the bride’s bouquet as well!

Beauty by Ann Krause added some romantic curls to Bree’s bob and created a perfectly soft + rosy-lipped bridal glam.

Explore our guide to wedding hairstyles for short hair if Bree’s look has you feeling inspired.

The Ceremony

This massive, circular hanging installation!! We are speechless!

“We tied the knot on a perfect fall day at The Joinery, a stunning venue in Logan Square, Chicago” recall Bree + Jake. “As Chicago locals, it was important to us that our wedding felt like ‘our Chicago,’ and The Joinery’s intimate yet industrial vibe fit our vision perfectly. Guests loved the neighborhood’s charm and the cozy, welcoming atmosphere of the venue.”

How cute are these custom matchboxes!

One of the couple’s favorite memories? “Having our best friend, Kyle, officiate the ceremony in the round, creating an intimate and heartfelt experience.”

Changing up the traditional wedding ceremony layout like Bree + Jake did is such a great way to make something unforgettable out of your “I do’s” for both you and your guests. Check out our creative ceremony seating setups for even more ideas!

Another favorite element? “Our vows—filled with laughter, tears, and so much love.”

We’ve got a super helpful article all about how to write your own vows if you want to add some meaningful, personal words to your ceremony like Bree + Jake.

The Reception

The wedding’s ceremony space was totally transformed for the reception! What a brilliant reuse of those hanging florals!

One of the couple’s favorite DIY projects? “Bree used her Cricut to craft personalized name cards for each guest.”

Two other amazing DIY details were the Memory Board (a memory board featuring heirlooms and photos from their grandparents to honor their legacies) and the Crazy Kids Wall (a wall of childhood photos of Bree + Jake to add a “playful and nostalgic touch”).

How adorable are these custom beer coozies!

Our Advice
The best wedding is the one where guests leave knowing more about you as a couple. Stay true to your vision, embrace what makes you unique, and focus on creating an experience that feels authentically yours. Trust us—it’s worth it!

The wedding meal was super meaningful memory for the bride + groom: “Serving family-style wood oven pizza from Wooden Paddle for dinner created a fun and communal dining experience.”

Bree + her dad went for “In My Life” by Johnny Cash as their father-daughter dance song…

… and Jake’s mother-son dance song was “God Only Knows” by The Beach Boys.

How delicious does this fresh raspberry-topped vintage wedding cake look!

Molly’s Cupcakes decked out the dessert table with all sorts of scrumptious sweets.

We’re obsessed with Bree’s outfit switch into this short wedding dress by Ronny Bass Bridal. And that pair of white wedding day cowboy boots? Perfection!

Our Musical Choices
Processional
“Till There Was You” by The Beatles + “The Wonder of You” by The Villagers
Recessional
“I Do, I Do, I Do, I Do” by ABBA
First Dance
“The Way You Look Tonight” by Frank Sinatra / “Fell in Love with a Girl” by The White Stripes

“Our last song of the night was ‘Love Story’ by Taylor Swift,” remembers Bree of her final moment on the dance floor with DJs Toast & Jam. “It turned into a full wedding interpretative dance and could not have been more magical to have everyone swarm Jake and me at the very end of the dance circle.”

The couple created massive custom pet head cutouts of their cat Mabel to make sure their feline family was represented on their Big Day.

The Grand Exit

On their way out the door, Bree + Jake donned custom airbrush t-shirts.

“We had our wedding shot on Super 8 film,” say Bree + Jake of their beautiful wedding video by Studio Zwerveling. “We didn’t want an overly produced wedding video, and it was perfect! It was also an homage to Jake’s grandparents, whose 1940 wedding was filmed on a Super 8 camera.”

“Green Wedding Shoes celebrates couples who infuse their weddings with creativity, individuality, and meaningful moments—and that’s exactly what we did,” add Bree + Jake. “We’ve been longtime readers of GWS, and it inspired much of our planning. Sharing our story with your community feels like coming full circle.”
Congrats, Bree + Jake! Your whimsical Chicago wedding was so beautiful and so you. Lots of love to you both!!