I'm so excited to be working with you and I can’t wait for our time together during your engagement session! It’s normal to be a little nervous about your session. I always tell people that I still get nervous before having my photos taken - and I do this for a living!

I love engagement sessions for a few reasons. First, they allow you to get comfortable in front of the camera. It takes time for most couples to warm up to being photographed and understand how I work. Timelines can be pretty tight on weddings days and 30 minutes may be all we have for portraits - which is why I’ve found that wedding day portraits turn out so much better when couples do engagement sessions ahead of time. 

Second, you can showcase your personalities in a more casual setting that is signficant to the two of you (and even include pets!). While they’re great for save-the-dates, I’ve taken engagement photos anywhere from 18 months in advance to a few days before the wedding. 

If you’re feeling a little nervous or have a million questions - that’s totally normal! This guide should help you feel prepared & excited for your session. 

We’ll cover what to wear, whether to bring pets & how to manage them, location ideas and more! 

- Kate

I get it. Having your picture taken for 1-2 hours might not be in your top-10 favorite things to do during your downtime. And at first you might feel sort of awkward being in front of the camera. But I think you’ll find that by the end of the session, it’s a lot easier than you thought, and you even had a little fun. I look forward to it because it’s a great opportunity for us all to hang out a bit before the wedding day.

The skeptics

a note for

Engagement sessions can take place anywhere from immediately following a proposal to just a few days before the wedding. I’ve found that there isn’t a “good” or “bad” time to take your photos. I normally plan sessions based on a particular “look” a couple has in mind, fall colors for example, or based on schedules. 

Sessions typically last about an hour or so and when possible — I love to begin sessions about two hours before sunset. I prefer to shoot when the sun is lower in the sky to avoid harsh shadows and bright sun patches. The first two hours after sunrise is also an ideal time to shoot.

I schedule sessions during what I believe will be the best light of the day - which means that it’s super important to be on time. If you’re late to an evening session, we could run out of light before we’ve finished shooting and if your session takes place in the morning, the sun gets more harsh as it rises. 

Is there a "good" time to take photos? 


While I shoot most engagement sessions between April and late November, sessions can take place all year. Most couples choose a season based on the location where they want to shoot. 

A few things to keep in mind during each season:







snowfall, hot cocoa and cozy coats

If you’re planning to take your engagement photos during the winter, keep in mind that if your session takes place in the evening, we could begin shooting as early as 2:30pm to catch the sunset. I recommend dressing in layers so that in between photos you can warm up. Make sure you bring a little extra makeup and tissues in case your nose begins running. 


fresh flowers and sunny days 

Even though Spring begins in March, I typically don’t begin shooting for another 4 weeks because the weather in Chicago is still pretty chilly. When I schedule spring dates, we typically schedule both a primary date and a backup rain date. 






sunglasses, ice cream, and picnic blankets

In spite of the heat, I'm a big fan of summer sessions! Because of the later sunset, sessions sometimes begin as late as 6pm. If you’re taking your engagement photos during the summer, I recommend bringing extra makeup and a few towels to make sure you stay fresh throughout your session. 






colorful leaves and snuggling close

Fall is one of the prettiest times of the year and because of the perfect weather, my schedule typically books up quickly! If you have your heart set on a fall engagement session, I recommend scheduling it as soon as you book! 





If your wedding is local, save the dates should be sent between 6 and 8 months before the wedding. For a destination wedding, you’ll want to send them out 8 to 10 months before the wedding. 

If you’re hoping to use your engagement photos for your save the dates, I recommend scheduling your session at least two months before you plan to send out your save-the-dates. Between inclement weather, editing, designing your save-the-dates and printing, two months is generally a safe amount of time to make sure your images and cards are ready. 


I’m happy to chat & help you find a location that excites you. 
There are several gorgeous locations in the Chicagoland area that have a variety of good things to offer!

Chicago Riverwalk
Millenium Park
Milton Lee Olive Park


Glencoe Beach
North Avenue Beach
Lighthouse Beach


A Vineyard
Tree & Flower Farms
Fabyan Forest Preserve
Waterfall Glen


 Sailing / Boating 


Wilder Mansion
Chicago Botanic Gardens
Wrigley Building Chicago
Mills Home Park




I love when couples choose a location for their session that shows their personality or tells a story about their relationship. We want these photos to feel 100% true to you as a couple. A special location is one way to come away with images that represent your unique relationship. If you love the outdoors, let’s find a gorgeous forest preserve! Live in the city & love all things CHICAGO? Let’s shoot downtown! Want some fun photos at your favorite brewery? I’m down.
If it speaks to you & excites you - let’s go there.

I'm a little obsessed with my dog, which is why I LOVE when couples choose to incorporate pets into their session. Keep in mind that bringing a pet along often means that we’ll need to choose a pet friendly location. 

I recommend planning for your pet to be at the first part of your session and then either dropping them off or having a friend take them home. We won’t use the pet in every single photo so it’s also nice to have a friend available to hold him or her in between shots. 

If you’re going to bring a pet, I recommend exercising your pet before the session and bringing your pets favorite toy or treats! Depending on your pet’s fur type, it might also be a good idea to groom them before the shoot. 



+ feeling YOUR BEST

When picking outfits I recommend keeping in mind the word “complement” rather than “match.” For example, if you are wearing a  white button-down shirt, your partner may want to choose a long, soft blush pink dress. It can also be a great idea to choose “color-families,” such as pastels or jewel tones. I've got a Pinterest board full of inspiration for you!  View pin board.

Most importantly, you should feel comfortable & confident. Some couples love a good excuse to get all dressed up & others prefer a more casual vibe. You could even do both! I bring a pop-up changing tent with just in case an outfit change is in order. Either way, if you choose clothes you feel good in it will show on camera. Go with your gut & don’t feel pressured to wear anything you don’t like.

Heels lengthen legs but if your heels aren’t comfortable for walking, bring an extra pair of shoes to slip into in between shots.

We love the way larger patterns photograph - just be careful not to choose a pattern that is too small - it may accidentally make your photo look a little too busy.

Softer, pastel colors tend to photograph better than bright colors - especially since bright colors could reflect on your skin. Bright, neon dresses can be fun, but the neon reflection they add to your complexion is not fun. 

Wardrobe Tips

Jewelry is a great way to add color or pattern to a simple dress. Lace and tulle look amazing in photographs.

Layers tend to photograph nicely so you could consider a cute jacket or scarf. Depending on your location, you might want to consider a fit and flare or a flowy dress!

They look great in walking and photos with movement. Choose an outfit you feel comfortable in, but don’t be afraid to dress up!


J. Crew
Free People

Favorite Shops

Engagement sessions are the perfect time for a hair and makeup trial! Professionally done hair & makeup last longer than typical hair & makeup. They also tend to hold up better for humitiy and wind.

I think it’s so important that you look and feel your best for your engagement photos - and if you’re planning to do a hair & makeup trial anyways, the engagement session is a great time to test how your hair & makeup look on camera.

Hair & Makeup

There will probably be times during your session when I'm shooting your hands holding or the engagement ring on your hand - which means it’s a good idea to clean up your nails before your session (this applies to the guys too!).


You can’t go wrong with a suit and tie. Consider pulling out that suit you had to wear last time you were a groomsmen! Layer with a blazer and a fun tie - you can even wear jeans with this look. Find ways to show your personality!

Be careful not to choose a pattern that is too small - it may accidentally make your photo look a little too busy. Softer, pastel colors tend to photograph better than bright colors - especially since bright colors could reflect on your skin. Cozy sweaters layered over button ups are a great way to stay warm and stylish during the cooler months.


Inclement Weather

what to do if it rains

Sometimes we schedule two engagement session dates, a primary date and a rain date. Having two dates helps us make sure that your photos happen in a timely manner. Another option is to have a back-up indoor location in mind.

I’ll check in the week of your engagement session to confirm the time & location we’re meeting and the weather. I know it takes a lot of time to get ready for engagement session and it’s the worst to get dressed up and drive out to your session only to have it rain. Let me know what works best for the two of you - but if the weather looks like it won’t be great, I typically try to make the call at least 8 hours in advance. 

When I can, I always try to take a photo of your ring during your engagement session - so it’s a good idea to have it cleaned or clean it yourself before your shoot! To clean at home, soak your ring in warm water with dishwashing soap for 20 to 40 minutes. Then gently brush the stone with a soft toothbrush, rinse and repeat if needed.

Ring Cleaning


champagne is always a good idea

If you’re planning to bring props to your engagement session, I recommend including them only if they’re meaningful to you and will help tell your story.

I completely understand how awkward it can feel to be in front of the camera. But I promise, there’s no need for worries like “Does this look right? What should I do with my hands?!” My job is to give you as much guidance as you need & make the whole experience fun & easy for you.

Think of your session like a date, it’s a time to take a break from wedding planning & other things going on in your life, you can just focus on each other & have fun with it! If I tell you to do something that feels a little funny, it’s probably because I know it’s going to make the two of you laugh - and that’s the photo I'm actually looking for. 

Throughout your session, I’ll keep an eye on your hair, makeup and outfits to make sure things stay in place. I want you to feel as relaxed as possible and enjoy your time together!  

"What do I do with
 my hands"?

"What do I do
 with my hands"?


Date Night

If you’re anything like me, you probably don’t get dressed up all that often. Which means that the day of your engagement session is the perfect occasion for a date night (or brunch if your session is in the morning!)

The engagement session is another part of celebrating your love and heading off to dinner is a great way to end the session!

After your session, your photos will take about 2 weeks to arrive in your personalized online gallery. Thank you so much in advance for being patient with me! You can download the photos directly and have the option to order prints through me! Once you have your photos, feel free to share on social media. I simply ask that you credit my business @katekaplanphoto and that you do not put filters on any photos or alter them in anyway.

When to Expect Your Images

I know that this guide is long and hopefully it covers everything you need to know to prep for your engagement session! However if there is something I missed, or you need a recommendation feel free to email