Adventure Sessions

Planning your Chicago engagement session can be stressful. Where should you do it? What should you wear? What time should the session be? Below we'll share some tips for how to get the most out of your Chicago engagement session. We'll take away most of your stress and help you prepare for an incredible adventure.

What is an adventure session?

We call our engagement sessions "adventure sessions." An adventure session is like an engagement session, but not. For us, the adventure session is about more than just capturing a photo for your save the date. It’s about creating memories, exploring new places, getting to know one another, experimenting, and developing trust. It’s also step one in creating your visual legacy.

In your adventure session you’ll:

  1. Get accustomed to our process and way of directing so that on your wedding day, you’ll have one less thing to worry about.
  2. Grow closer to one another. Our approach to adventure sessions is all about connection and having fun. We’ll direct you in ways that allow the two of you to connect on a deeper level. And you’ll probably laugh a lot.
  3. Learn to embrace the awkwardness of the process. Let’s face it. Having pictures taken of yourselves is a pretty awkward thing to do. In your adventure session you’ll learn to embrace awkwardness and trust the process.
  4. Create new memories with one another. Ultimately the adventure session, just like your wedding, is about having an incredible experience and creating new memories. Our approach is very relaxed. We’ll pick a location, explore, experiment, and have a lot of fun. In the end, you’ll create new memories, experiences, and maybe even a story to share.
  5. Get some epic photos of the two of you. We typically deliver around 30-40 photos per adventure session.

Where should we do our session?

Lincoln Park Engagement session photo

There are so many choices when it comes to picking a location for your adventure session. We could go to the Warren Dunes at Sunset and take epic photos that look like you’re in the middle of the desert. Or we could shoot at the Adler Planetarium and create incredible photos with the Chicago Skyline in the background.

Here are our favorite places to shoot for your Chicago engagement session (check out our blog for more examples):

  • Montrose Harbor/Beach
  • The West Loop (urban/murals)
  • Museum Campus/Adler Planetarium
  • Lincoln Park/North Avenue Beach
  • Flower Fields (seasonal)

It might be tempting to try to fit in two or three locations. However, we recommend choosing one location that provides a little variety within walking distance. This is important because having to hop in the car to switch locations takes up precious time and light that we could be using to get great photos. It also breaks the flow of the session.

So, pick one spot that you’ve always wanted to explore, but remember less is more. And remember, we could always do an anniversary session at another location! Your visual legacy doesn’t have to be created in one day.

What should we wear to our session?

San Juan Capistrano Engagement

Choosing the right outfit is a very personal decision. Ultimately the choice is up to you. We recommend choosing clothes that are both comfortable and fit your personality. That might mean you wear jeans and a button-up shirt. Or he might wear a suit and you a flowing red dress. Or you both might wear suits.

The decision is yours, but we do have some suggestions that might help narrow it down:


  1. Do dress for the weather. If it’s cold outside, try to avoid open-toed shoes and short dresses. If it’s 90 degrees out, you may not want to wear a tux that you’re going to be sweating in. Your comfort will matter a lot more in terms of the quality of your photos than the actual outfit you choose.
  2. Do express yourself with your outfit choice. Feel free to wear bold colors or keep it simple with jeans and a sweater. Whatever you do, be you.
  3. Do feel free to get gussied up before your session. The day of your session is a great time to get your hair done and do a test run for your wedding day makeup. While it’s not a requirement to get great photos, you’ll be happy you went the extra mile to look your best for your session.
  4. Do wear complimentary colors. While you want to avoid matching too much (as we’ll talk about below), complimentary colors can make your photos pop.
  5. Do feel free to wear a hat if that’s your thing.
  6. Do feel free to bring an additional outfit if you want to, but consider that we’ll have to stop the session and find a place for you to change which will reduce the number of photos we’re able to take. The typical outfit change takes about 30 minutes.
  7. Do feel free to include your dog in the beginning of your session, but make sure you have someone with you who can take the doggo home after the first 15 minutes or so. We love dogs! But they tend to be a distraction from the session if they’re there for the whole thing. (This isn’t an outfit thing really, but it’s an important consideration.)


  1. Don’t wear shorts. I can’t explain why. Just trust us.
  2. Don’t wear shirts with a logo on the front. We love Nike as much as the next person, but that swish can be distracting in photos.
  3. Don’t wear clothes that are too matchy matchy. If your fiancé is wearing a green dress, don’t wear a green shirt (try a complimentary color instead, try this color wheel to find great complimentary colors).
  4. Don’t wear shoes that aren’t comfortable to walk in. Also, try to avoid high heels as we will probably run for at least one or two photos (and we rarely include feet/shoes in our photos). On most sessions we’ll walk over a mile. If you wear your Louboutin heals, your feet might look great, but they’re probably going to be bleeding by the end of the session. So go simple, but elegant. Also, consider the location and weather.
  5. Don’t wear outfits that have overly complex patterns (simple stripes or patterns on dresses/shirts are fine). Complex patterns have a tendency to distract the viewer from the main subject, which is the two of you. Simple and solid colors tend to be preferable to an outfit with a lot of distracting elements. We’re not saying you can’t wear anything with stripes or patterns, just choose wisely.
  6. Don’t stress too much about your outfit choice. The perfect outfit is the one that you’re comfortable in and that makes you feel good about yourself. So keep it simple and have fun with it!

What time of day should we do our session?

Best wedding photographer Chicago

Good light matters more than any other factor when it comes to planning your session. We typically suggest that we begin your session about two hours before sunset, because by the time the light becomes golden and magical, you’ll be getting comfortable with the process.

But choosing the right time also depends on the location, the weather, and the time of the year. If we’re doing your session in the Rocky Mountains and we’re on the eastern side of the mountain, then your session will need to be earlier. The same goes for a session in Grant Park as the sun will disappear behind the buildings earlier than sunset. We’ll work with you to make sure that we pick the right time for your session, but more likely than not it’ll start two hours before sunset.

How can we get the most out of our Chicago engagement session?

Chicago Engagement Photo Tips

Here are some final tips for how to get the most out of your Adventure Session:

  1. Be Present. When you arrive at your session, leave all the other thoughts and worries of your day in the car. Try to stay in the moment and enjoy the experience.
  2. No Worries. The second most important aspect of taking great photos after good light is how the two of you are feeling. So don’t worry too much about the details. Pick a place, an outfit, a time, maybe have a drink before your session, and then let go. It’s our job to guide you through the process and take great photos of you. So all you have to do is follow the tips above, then relax and trust us.
  3. Come into the shoot with an open mind and open expectations. Try to avoid looking at Pinterest or other people’s engagement sessions. Just like your wedding, your adventure session is going to be different than anyone else’s. If you come into the session as a blank slate, it’s more likely that we’ll be able to take the best possible photos for you and create something that is unique to you, not a copy of what someone else did. It might seem helpful to send us inspiration photos so we know what you’re looking for, but in reality, it will simply place limits on our creativity and make it harder to do what you hired us to do. So come to your session with an open mind and we’ll make magic together.
  4. An adventure session is different than your wedding day. While on your wedding day 90% of the photos we take will be candids, on an adventure session most of the photos will be directed. That means that if you love us for our candid photos, you’ll want to reset your expectations for the adventure session. While we will certainly shoot through the moments and try to capture the natural interactions between the two of you, these photos are mostly going to be portraits.
  5. Trust the process. This is probably the first time you’re having professional photos taken of yourselves, so it’s natural to be anxious and try to take control of the outcome of the session. An adventure session, however, is a lot like jazz. While there are some parameters for the session such as the time and the location, the best art is produced when we follow our gut and let the light and inspiration lead us. Great photos are part good planning and part improvisation. If you’re a planner, that might be unsettling, but it’s the only way we know to create something truly unique. We’ve done this hundreds of times and you hired us because you loved our work.So, all you need to do is trust us to guide you and take great photos. And in the end, you’ll hopefully receive better photos than you could have imagined.
  6. Have fun!

Share this story