Chicago Couples Photoshoot | Kaylie + Dion

Okay, let me just say—Kaylie and Dion totally brought it for their Chicago couples photoshoot. This session had everything: fancy vibes, grungy vibes, and a whole lot of love. It was basically like shooting two completely different date nights, and I was here for all of it.

From Red Carpet to Riverwalk

We started off on the Riverwalk, and Kaylie and Dion were straight-up glam goals. Kaylie showed up in a black dress that would make the Oscars jealous, and Dion? Absolutely killing it in a sharp suit. The Chicago skyline gave us that perfect mix of classy and cool, and these two looked like they were shooting the cover of a romance novel.

Next Stop: Edgy City Feels

Then we did a total 180. Kaylie and Dion switched it up, went full grunge, and we hit the subway for a completely different vibe. The gowns and suits were swapped for bold, edgy outfits, and they absolutely owned it. Between the L, on a subway car, and that gritty city energy, it was like a whole new love story—Chicago edition. It was the perfect way to capture all the personality and edge of a Chicago couples photoshoot.

One Couple, All the Vibes

What made this shoot so fun was how Kaylie and Dion totally leaned into both looks. One minute they were giving off “we’re headed to a gala” energy, and the next it was “we just jumped out of a punk rock music video.” And honestly? Both were perfection.

Chicago, you were the ultimate wingman for this shoot. And Kaylie and Dion—you two are just cool. Can we do this again next week? 😊