Meeting Jayden + Free For Their Engagement Session

Last November, I spent over three hours with two of the most incredible people, Jayden and Free, running around capturing their engagement session in Chicago. And let me tell you—it was a blast. DJ joined me for the session, and we had so much fun getting creative together. Their engagement gallery is such a seamless blend of both our work, and I love how it all came together.

Jayden and Free’s story started years ago as close friends, and somewhere along the way, their connection grew into this magnetic, goofy, head-over-heels kind of love. Spending time with them was like getting swept into their energy—full of laughter, light, and so much heart.

Our History

I actually met Jayden and Free for the first time back in August 2022. Jayden reached out wanting maternity photos for their little girl, Cruz—who, by the way, is equal parts sweet and sassy. At the time, they were engaged, so we threw in some playful nods to that during the session. Fast forward to October of this year, and I had the honor of documenting their wedding day in Springfield, Illinois.

This is my favorite part of what I do—being able to follow along in a couple’s story. From their maternity session to these engagement photos to their wedding, I’ve had the privilege of capturing some of their most important milestones. Watching them grow as a family has been so special, and I’m just so grateful to be part of their journey. Jayden and Free, I adore you—as parents, as partners, and as humans. You two are just everything.

The Outfits

Jayden and Free’s session was such a perfect example of how to bring a little personality and pop into your outfits. Jayden absolutely owned her look—a white dress paired with hot pink heels that were bold, playful, and so totally her. The heels added such a unique, personalized vibe to their gallery, and honestly? They just made sense.

Free complemented her beautifully in all-black attire, and together, they had this clean, classic look with a bit of edge. Later in the session, they switched into more casual outfits, which were perfect for running around the city. Jayden rocked a black overcoat, brown sweatshirt, and light-wash jeans, while Free wore a jean jacket, black shirt, and dark jeans. Their looks felt effortlessly in sync—matching just enough without being too matchy-matchy. Jayden and Free’s outfits were truly perfect for the two of them, the season, and the vibes that they were going for. Their attire was even more so perfect for the locations that they chose for their engagement session in Chicago, which we talk more about now!

The Start To The Day: The Chicago Board Of Trade

We wanted to highlight their love for Chicago by capturing their session in some of the city’s most iconic spots because they love the city so much (me too). As you may know, we go to lots of different beautiful locations in Chicago depending on what the couples wants for the vibe of their session. It was so hard to choose the locations to narrow down for these two, but overall I think our choices were perfect and reflected Jayden and Free’s love for each other and the city perfectly. First up: The Chicago Board of Trade. This location is stunning, with its historic architecture and urban energy. We shot everything from romantic spins in the street to sultry moments up against the towering buildings.

Next Up: Outside The Civic Opera House and The Chicago Theatre

Next up during our iconic engagement in Chicago, we wandered over to The Civic Opera House, which was a beautiful art deco vibe to add to their engagement session. We didn’t capture any photos on the inside, but we did hang out outside of the building for a change of scenery in the same outfits. This location is so perfect because just around one of the corners you can find one of the iconic Chicago bridges to do photos on as well which is always fun and a must to capture the river, bridge and any passing boats!

We also ended up going to The Chicago Theatre, which is one of the staple landmarks in the Chicago area due to the big, beautiful, and truly iconic marquee that says “Chicago” on the front of the building. I have done quite a few sessions in this area because of how iconic it is; I also lowkey love that when you’re capturing your engagement session here, you can see what was playing there that day when looking back at the gallery. We did these photos in the casual outfits that we talked about before, running around in the street and capturing so many photos in the area around the theatre. These turned out so playful and stunning and even led to Jayden’s idea of going down into the subway nearby – which I LOVED!!

The Subway Photos

One of the most iconic photos that I feel like DJ and I have captured that really screams Chicago, is the part of our day where we took a quick visit to the subway station by The Chicago Theatre. This was completely all Jayden’s idea and the perfect end to their sesh. In the casual outfits that they brought for the session, we headed down to the subway and captured some fun photos of them in front of the moving train cars. These photos truly focus on the two of them having a moment together as the world moves on as normal behind them. There’s something so cinematic about it—it perfectly captures Jayden and Free’s story. The movement, depth, and raw emotion radiating from these subway photos makes them absolutely unforgettable.

Overall, this engagement session in Chicago was such a dream and I cannot put into words how much it means to me that these two have continued to come back to me to capture all of the important moments in their life. If you would also like to work with us to capture your love and so much more, do feel free to fill out our contact form and we will talk as soon as possible!!