Kaitlyn and Jacob’s engagement session? A full 10/10. No notes. Straight out of Vogue.

From the second Kaitlyn told me her vision, I knew we were about to create something iconic. Chic. Editorial. A little Gatsby drama. And she absolutely delivered. With their wedding day inspired by vintage glamour, this session was the perfect preview, refined, bold, and fashion-forward in all the right ways.

We started at Vol. 39 (a whiskey bar inside the Kimpton Grey hotel, which I’m obsessed with), and the moody lighting was everything. Rich tones, elevated textures, a little mystery — it gave us those cinematic, editorial moments that feel like you stumbled into a high-fashion campaign instead of an engagement session.

Then came the outfit change — and wow. You would’ve thought Kaitlyn had a full glam squad for part two. Nope. Just a few perfectly placed bobby pins and pure talent. Icon behavior.

The Board of Trade backdrop paired with lace umbrellas and custom save-the-date newspapers? It was giving old-money romance meets modern city chic. The kind of styling that makes my creative heart so happy: sophisticated and structured. 

What I loved most was how natural they still felt in it all. Yes, it was styled. Yes, it was elevated. But it was also playful, romantic, and so very them. That is the beauty of engagement sessions: make these moments feel like you. 

View Kaitlyn and Jacob’s full engagement session gallery here.