A Guide to Prepare for Your Engagement Photos in Chicago

An important piece of your journey as a couple is your engagement, and while it doesn’t normally get the same level of celebration as your wedding day, that doesn’t make it any less special. As such, engagement photos are some of my favorite to document in Chicago. Just like a wedding day, there is a lot of planning that goes into these sessions, which is what we’re here to discuss today! From what to wear for your engagement photos, to how to prepare for the session itself, we’ll cover it all here.

Book Your Photographer

The very first thing you’ll want to do is of course find and book the photographer that will be taking your photos. I always recommend booking the same photographer for both your engagement session and your wedding day. I find this extremely helpful for SO many reasons. It allows you to get to know your photographer prior to the big day, get comfortable having professional photos taken of you, and it gives your photos a cohesive style throughout. Head to my experience page if you’d like to take a look at my engagement and wedding packages.

What to Wear

One of the most important aspects of planning your engagement session is deciding what you’ll wear for your photos. Not only do you want to look good, but you also want to be feeling good for your session. If you’re uncomfortable, or not quite sold on an outfit, it WILL show in your photos. I can assure you of this, as like so many others out there I have definitely shed tears over some past outfit choices! This is the LAST thing I want you to feel when looking through your engagement photos, so let’s go through everything you need to know when planning out the outfits you’ll wear for your session in Chicago.

Season and Location

The season and location of your engagement session each play a huge role in the outfits you choose. If you plan on having your session in the summer for instance, then wearing a sweater is probably not the call. You want to choose outfits that are appropriate for the weather and temperatures that you can expect each season. Consider also the attire or season you both enjoy the most. For example, if you both adore Chicago in the winter, or plan on having a winter wedding, you may want to take your engagement photos during the winter.

The location of your session will impact your outfit choices, though in a different way. If you intend to have your session in one of Chicago’s beautiful parks during the summer you can expect a lot of green backdrops. Knowing this, you’ll want to avoid wearing any greens so that you don’t blend in, and instead wear complementing colors. You also want to make sure that your outfit doesn’t feel out of place at your location. If part of your session takes place at a classy restaurant in Chicago it’s probably best to wear an outfit that’s a bit more formal!

Choose a Color Palette

Now that you know when and where your session will be, it’s time to figure out your color palette. My favorite way of doing this is by browsing Pinterest using search terms like “Midwest summer color palette” or “October field color palette” that relate to your season and location. Browse through these results with your boo until you find one that speaks to you both!

Choose Your Outfits

Once you have a color palette, it’s time to start putting together your outfits. I find it makes things easier when one person chooses an outfit that they love and then the other person builds their outfit to complement the first. Stick with the color palette you’ve chosen, and consider the following points when choosing the outfits you’ll wear for your engagement photos in Chicago.

Stripes and Patterns

You and your love are the focal point of your engagement session, and as fun as stripes and large patterned clothes can be they are often distracting. Especially when it comes to photos, stripes and patterns can end up giving your bodies some weird effects on camera. Smaller, less invasive patterns like smaller florals or understated plaids can work, but there are much better ways to add personality to your outfits. Like…

Textures

I LOVE textures and always get excited when my couples include them in their outfits. There are so many fun and unique ways to add in a mixture of texture to your outfits. Ribbed knits, linens, and velvet all typically photograph beautifully, and they add a fun level of visual intrigue to your outfits without becoming overbearing.

Matching vs Complementing

It’s almost always in your best interest to avoid matching one another when planning out the outfits you’ll for your engagement photos in Chicago. Unless you two match all the time and it’s part of your distinct style, it’s best to avoid it all together. Matching colors can lead to your bodies looking as though they’re warping together in your photos. Instead, I recommend wearing colors and outfits that complement one another. Think back to your color palette and try to stick within those options for your outfits!

Accessorize!

One great way to add a bit of personal flair to your outfits is through accessories! Whether it’s a classy watch that was a gift for Christmas, or a set of earrings given as an anniversary gift, the right accessory can really complete an outfit. Much like the rest of your outfit planning, keep your accessories simple and tasteful for your engagement photos. 

Comfort is Key

I mentioned earlier that not fully loving your outfit is going to show in your photos, which is why your comfort is essential for your engagement session. Comfort is about more than just the physical aspect though. Choosing clothes that make you feel confident plays a huge role in your comfort during a session. Don’t opt for a huge style shift for your engagement photos, and instead wear clothes that feel true to YOU. 

Preparing for the Session

Now that you’ve booked your photographer, chosen a season and location for your session, and found the outfits you’ll be wearing, it’s time to prep for your session!

Try on Your Outfits

Before the day of your session arrives you’ll want to try on your entire outfit. Make sure you like the way everything is fitting, the way it looks on you, and that it all looks good together alongside your future spouse’s outfit. A pro tip I have here is for anyone that gets new shoes for their outfit.

Break. Them. In.

You’ll be spending a lot of time walking around and on your feet during your engagement session, so the last thing you want is to be in a pair of uncomfortable shoes!

Relax Before the Session

Take things easy the day of your session. If your session is on a weekday, take some time off from work if you can. For a weekend session, take the morning nice and slow and enjoy some quality time together. Go to your favorite coffee shop or breakfast place to start the day off on the right foot. This will help you go into your session relaxed and in a great mood.

Hydrate!

It’s important to hydrate the day of your session, and even the week leading up to it. We all know how important proper hydration is, and it’s no fun being lightheaded and tired while having your photos taken. I want you to enjoy having your engagement photos taken in Chicago to the fullest, and taking care of yourselves is an essential part of that!

Keep an Eye on the Weather

The Midwest loves to keep things interesting when it comes to the weather. Especially in the fall and spring seasons, the weather of Chicago can be highly unpredictable. Keep an eye out on the weather forecast the week of your session so you have an idea of what you’ll be dealing with. Your photographer should also be watching the weather, and will be in contact if things are looking dicey for the day of your session.

Make a Date Night of It

Last but not least, make a date night out of your engagement session. Think about it, you’re already all dressed up, you’re out and about in Chicago, and you have an engagement to celebrate! It’s the perfect excuse for an unforgettable night out in the Windy City celebrating your love and this new chapter of life you find yourselves in!

That’s just about everything you need to know to prepare for your engagement photos in Chicago. If you’d like to have me document this incredible time in your lives be sure to send me an inquiry through my contact page today. I’d love to hear from you, get to know you both, and help plan out the perfect engagement session for you!

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Hi, I'm Carissa. My deepest desire is to care for you and take care of every background detail so that when you step in front of my lens, you can be your full, raw, honest self--undistracted by flyaways or timelines or what to do with your hands.

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