Chicago Engagement Photos Round 2 (+ Advice!)

Hello, friends! Since Kerri sent me our full album of engagement photos, I thought it would be fun to do a little wedding Q&A… but then I quickly realized you guys had LOTS of questions! So big thanks to all of you who voted in yesterday’s poll, because I’m going to focus on engagement photo questions today – and then next week we’ll tackle all of the wedding questions! I promise, I won’t make you wait long!

In case you’re new around here, Adam and I took engagement photos with our original photographer back in 2019. And if that feels like a long time ago… ummm… IT WAS. We got engaged December 2018 with plans to get married May 2020. Obviously COVID had different plans for us, we postponed our wedding 3 times, and now it is actually finally happening at a completely separate outdoor venue at the end of August.

There were definitely a lot of tears when saying goodbye to our dream venue, our wedding weekend in the city, and the whole vision we had for our day. But in addition to that, we also had to say goodbye to our amazing photographer too. I genuinely wasn’t sure what we were going to do since so many photographers are booked solid this summer due to all of the postponements from last year.

But somehow the stars aligned and Kerri Carlquist was available! And instead of crying sad tears that day, I cried very happy tears!! We had a long phone call about the new plan and she offered to take new engagement photos for us so that we can get to know her in person before the wedding, but also to help us get excited about getting married again… and it totally worked! 

 

Engagement Photo Advice

Suggestions for Chicago engagement photo locations?

I think this totally depends on your personality and how much time you have with your photographer! But let’s start with the obvious, because you really can’t go wrong with skyline shots in Chicago. North Avenue Beach is probably the most iconic view in Chicago, but we skipped that just because I’ve always wanted shots there on our actual wedding day. And yes, even though we’re getting married in the suburbs now, we are making that happen before driving out to the burbs!

Since we still wanted skyline shots for our first round of engagement photos, we took pictures down in Olive Park which was absolutely beautiful. If you’ve ever googled “Chicago Engagement Photos” or scoured Pinterest for inspiration, you’ve probably seen photos of this spot. It’s beautiful!

But that’s not all! You could also go down to Museum Campus, take photos on the bridge in the Lincoln Park Zoo, or even go down to the Riverwalk. You can’t go wrong with ANY of these, really.

On the other hand, I also think neighborhood shots are SO sweet. That’s why we opted to take photos in Winnemac Park this time around with Kerri! We walk Luna in this park nearly every day and it’s become so special to us. I always love the idea that engagement photos are an opportunity to capture what your relationship looks like in a specific moment in time – so why not make it really personal?

Where is your favorite place to take a walk? Or your favorite place to get coffee and pastries? Where was your first date? You can totally get creative and make sure the location really reflects you two as a couple.

How did you decide what to wear?

For our first photos, I really didn’t overthink my outfit choices at all. I wore jeans and a white shirt for our neighborhood shots, and a white floral dress for our skyline shots. I figured I wanted to look exactly how I would normally look for photos of us walking Luna near our old apartment – and then really bridal for our downtown photos.

This time around, I had less of a vision and I definitely overthought it. (It’s true 😂) I actually ended up purchasing this dress just a few hours before our shoot!! Nothing like a last minute decision, am I right? In all seriousness, I was searching for something romantic that accentuated my waist and covered my arms. That might seem weirdly specific, but most of the weight I gained during the pandemic has settled in my arms and I really didn’t want to be self conscious during the shoot. And it worked! This dress made me feel SO beautiful that I was completely in the moment during the whole shoot. Why waste even a second worrying about how an angle might make you look? You don’t have time for that! You only have time for joy and love, honey!

Where can I find more outfit inspiration for engagement photos?

I actually wrote a post all about What To Wear For Engagement Photos back in 2019! I spent some time updating it yesterday and I’ve made notes in my calendar to continue to update it throughout summer too. 

Ultimately, I think if you have time for two outfits – pick one casual and one dressier. If you only have time for one, pick the one that makes you feel the best. For me, that will always be a dress because I adore dresses. For you, it might mean boyfriend jeans and a t-shirt, because you never wear dresses. That’s cool, too!

Regardless of which direction you go in, just find something you feel amazing in.That is truly the most important thing when picking out what to wear. This way, you can be 100% in the moment and focused on having fun with your fiance. That’s what it’s all about!

 

 

Do you have any engagement shoot advice?

To piggy back off of my answer above, I think the best thing you can do is set yourself up to feel like your best self. Find something to wear that you feel beautiful in. Find a location that means something to you and your fiance. If you never wear heels, ditch them! If you never ever go downtown, take photos in your neighborhood! You want to be confident and comfortable and open to having a good time.

Which leads me to my biggest piece of advice – let yourself HAVE FUN! Engagement photos do not need to be so serious. You can be silly and crack each other up and ENJOY yourselves. Not only is that more fun in the moment, but it also shows in the photos. Some of my favorite pictures from this round are the ones where we are both laughing hysterically. Why? Because that’s what our relationship actually looks like. Our life together isn’t full of model poses, but it is full of laughs.

Need help planning your wedding?

Did you know that I created a Wedding Planning Bundle last year?! This includes a Wedding Planning Timeline that breaks down what you should be tackling each month and a Registry Guide designed to help you identify exactly what you need (and don’t need!). You’ll also get a Budget Template in the form of a Google Sheet that you can duplicate and edit specifically for your wedding. And lastly, a venue comparison sheet… because that process can get confusing and overwhelming real fast. I designed all of this to help you stay organized and confident throughout your wedding planning process – and I hope it helps you as much as it’s helped me! Click here to purchase!

PS. You might also like My Wedding Planning Bundle, What To Wear To Engagement Photos, Wedding Postponement Announcement, A Letter To Brides Affected by COVID-19, and Our 3rd Postponement.