Bistro & Beach Destination Engagement Session // Kailyn + Connor

Kailyn and Conner love to travel, explore, and try new experiences. They’re tying the knot at Grand Geneva on Lake Geneva, Wisconsin this year. But first, they wanted to do a romantic Lake Michigan engagement session in Chicago. (These two are drawn to the water!) However, this wasn’t just any waterfront location. We began their engagement session where they had their first date—The Kitchen on the river in Chicago. After reminiscing over drinks, we finished the photoshoot with stunning sunset beach photos. Both scenes fit them perfectly and gave more variety to their engagement photos. 

Instead of a styled session, Kailyn and Connor wanted at least part of their engagement shoot to have a lifestyle feel. Their first-date spot made this part of the session extra special, and I gave them some time and space to relax and relive that part of their story. I loved capturing the laughs and intimate moments as they simply enjoyed the views and reminisced on how far they’d come since that first date. It’s easy to get caught up in the whirlwind of wedding planning. Using your engagement session as a much-needed time to get away and enjoy each other’s company without a checklist in hand can be fun. Kailyn and Connor spent the session wrapped in bliss, which reflected so perfectly in their photos.

Tips for Your Lifestyle Engagement Session

Location is everything.

As an engagement and wedding photographer, I strongly recommend planning your engagement session at a location that means something to you. It doesn’t matter if I have shot there or not. I can easily scout it out and find the best spots, angles, and lighting for your photos. Most importantly, I want these photos to resonate with you and feel personalized and memorable when you look back at them years from now. When you select a sentimental location with more than a pretty background, your images will feel more cinematic, candid, and emotive—all the things people love about lifestyle photography. It’s not so much a look as it is a feeling. It’s a whole vibe, and your location can emphasize it even more!

Bring along the props!

Another way to enhance the lifestyle look is by bringing authentic props (think a blanket, picnic setup, and bottle of wine at the beach to watch the sunset). The colorful drinks at the bistro worked well as built-in props. You might even order a plated appetizer for photogenic lifestyle touch. Carrying coffee cups, a hat or umbrella, or walking the dog all work, too!

 Don’t be scared of patterns or color.

Neutrals always work well for engagement sessions, especially if you have no idea what to wear (feel free to ask me for tips!) But don’t be shy if you love color and patterns! Those can work well in photos, too. I loved Kailyn’s blue and white dress with subtle florals. He wore solid blue and white, so her pretty dress complemented the look and added a splash of color and texture without detracting from the two of them. (Her dress is Abercrombie & Fitch, btw—they have some adorable dresses that are perfect for photos.)

Mix it up – I’m down to travel!

You’ve heard of destination weddings, but do you know about destination engagements? If you’re like Kailyn and Connor, you may want to get away for a weekend to a new destination and take engagement photos on vacation. Let me know! We can book a destination engagement session even if you are getting married here in California. If you love the idea of using a meaningful location, but that location is out of state, let’s book a flight, and I’ll meet you there! 

Don’t skip the engagement session!

A destination engagement session can be so much fun, and I love getting to work with my couples before the wedding day. I always recommend doing an engagement session with your wedding photographer, even if you’ve done photos before. An engagement session with your wedding photographer is like a rehearsal, so you can get to know each other and warm up to the camera. Every couple is different, so I like to use the engagement session to learn your preferences and get to know you so I can be the most helpful and capture your chemistry on your wedding day.

Save the best for last.

Don’t start packing up yet! Once we get those golden hour sunset photos, there’s still more beauty in store for your session. For Kailyn and Connor’s engagement session, we waited past sunset into dusk to get the epic colorful skyline and dark images with flash. These can be fun, creative portraits to add to your engagement collection, and they often end up being my couple’s favorites. Plan to wait out the sunset because sometimes the best photos are still to come! Trust me!

Curious about Engagement Session Locations?

I’ve got you! Whether you’re a SoCal native or have other ideas in mind, I’d love to tell your story from behind the lens. Connect with me here

Destination, Engagement




Bistro & Beach Destination Engagement Session // Kailyn + Connor

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