Engagement Photoshoot Ideas for Chicago Engagement Photos That Tell a Story

Engagement photos shouldn’t be cookie-cutter. Ever. They should tell a story. They should give insight to who you are as a couple. Taking engagement photos deserves to feel less like checking a box off of a checklist, and more like going on a date with your favorite person, celebrating this season of life. Forget tradition, because epic, unique photos are where it’s at! As your Chicago engagement photographer, I’m bringing all the engagement photoshoot ideas you need to feel at ease and end up with photos that actually reflect who you are. 

Engagement Photoshoot Ideas from Sarah and Jack’s Chicago Engagement Photos

If you’re here, you probably aren’t the type of person who wants to put on a sundress, go to a field and be told to stand there and kiss thirty times while I snap pictures. And I get it, I’m not either! That’s why my approach to Chicago engagement photos is different. I want special locations. Unexpected poses. Funky outfits that actually feel like you. 

That’s exactly what Sarah and Jack did, and I’m so here for it. And their gallery? It evokes emotion. You can actually feel their personality in it. It doesn’t look like every other session you see. Love that. 

Here are a ton of engagement photoshoot ideas from their session, for your inspiration:

Choosing the Right Chicago Engagement Photos Location

The biggest factor in how your engagement photos turn out is the setting. Feeling comfortable in the location you choose is an actual game-changer, because if you’re in a stuffy space where you feel awkward and nervous… It’s gonna show. That’s why I’ll always recommend spots that you two know: a frequent date spot, a street that you guys walk on all the time, even at home. 

With Sarah and Jack, we followed this notion and went to Logan Square for some of their favorite spots. We started at Best Intentions and got some bar engagement photos that I’ll actually never get over. I mean, the jukebox, the lighting… Are you joking?!

We then headed to the Blue Line for some subway station shots that are giving rom-com vibes in the best way. The movement, the texture, the romance of it all was all toooo good. We took the train to their neighborhood and walked around there next, and the sun was setting and making the lights sparkle in all the right ways. Ugh, I’m obsessed. 

Engagement Photoshoot Outfits

The best advice I can give you for your engagement photo outfits: wear something that makes you feel like yourself. Because engagement photos aren’t for pretending to be someone you’re not, they’re for expressing yourself. Showing off who you are. 

Sarah’s outfits were straight-up dreamy. Her black dress fit the bar scene perfectly, then swapping to a more casual outfit for the subway and street photos. And this jacket?! Okay, love. 

Here are a few ideas for your engagement photo outfits that I can never get enough of: 

• Fun textures – think accents with feathers, denim, leather, etc. 
• A unique color palette – you don’t have to wear white, trust me 
• Vintage vibes – because you can never go wrong with a thrifted outfit 

An Outfit Change

Because self-expression doesn’t have to be tied to one look. But seriously, I love a two-in-one vibe for your engagement photos. You then get the opportunity to have one casual outfit, and one more dressy, or even one that’s funky and one that’s a little more mainstream. I’m always pro outfit change, honestly! 

Incorporate Fun Poses & Movement

When I’m your Chicago engagement photographer, you won’t just be standing still, smiling at the camera. You’ll be moving. I’m talking running, dancing, spinning… All the fun things!! 

My goal is to make your engagement photoshoot feel like a date. And on a date, you’re not robotic and just smiling at each other. So I’ll be prompting you in a way that feels gentle and natural, but never in a way that feels stiff or awkward. 

How Choosing the Right Chicago Engagement Photographer Makes Your Photos Feel Like You | Wren & Rose Photography

My approach to getting engagement photos that actually feel like you is making sure that I know you first. I spend the first little bit getting to know you two, what makes you laugh, and what you like to do, so that once it’s time to start taking pictures, we’re already comfortable with each other, and I know how to work with you. This establishes trust, which is a huge factor in how your photos turn out. If you don’t trust your photographer, it shows. 

So, if you’re looking for a Chicago engagement photographer who takes a funky, personalized, and editorial approach, I’m your girl. Let’s create a session that feels true to you, together. You can inquire about booking me here! 

While you’re here, get more engagement photoshoot ideas on my Pinterest and from these other blog posts: 

Unique Ideas for a Couple’s Photoshoot at a Chicago Dive Bar

Chicago Engagement Photos in Chicago Chinatown for Artsy, Non-Traditional Couples