WORDS AND PHOTOGRAPHY BY Stephanie Wood, Stephanie Wood Photography
Prepping for your engagement session sounds easy right? Until you realize you need to figure out where to go, what to wear, how to do your hair and makeup, how to include your pets and the list goes on and on. Well, not to worry — I got you, boo! I’m delivering my most bang- for-your-buck engagement session planning advice so you can have the stunning photos you’ve always dreamed of — stress free!
#01 | LOCATION, LOCATION, LOCATION
Just as it’s important to select your wedding dress after choosing your wedding venue, you want to decide on photo locations before you go shopping for outfits. It’s best to stick with two locations to maximize your time at each and then select one wardrobe choice per location.
So here are some things to consider (and discuss with your photographer) when choosing a location for your engagement session:
- What is the overall vibe you’re going for? (Urban architecture, street chic, urban garden, skyline views, etc.)
- What is the lighting like at different times of day?
- Are there permits you need to secure prior to the shoot?
- Do you have any places that are special to the two of you? The place you got engaged or your favorite date night locale make for great storytelling images.
- Plan ahead for transportation. For example, is it better to drive yourself or take a rideshare to photo spots?
Pro Tip: Double check the date of your session with any big Chicago events (street fairs, music festivals, etc.) — it’s no fun planning everything out and arriving only to discover you can’t access the location you were dreaming of.
#02 | CONSIDER YOUR SEASON
Do you love the fall but prefer a spring color palette? Do you love the look of snowy pictures but can’t stand to be out in the cold for more than two minutes?
Before scheduling your session and planning all your wardrobe and styling around it, take a moment to consider what season helps tell your story and how you want to feel during your session. If you just love ice skating together at Millenium Park and “the cold never bothered you anyway” then by all means go for that winter session. But if the idea of being outside in negative temps makes you tense up just thinking about it, it’s probably better to schedule something later in the spring or summer. Prioritize your experience over that one “must have” photo you saw on Instagram.
Pro Tip: Look up “Seasonal Color Analysis” online to discover which seasonal palettes suit you best!
#03 | DRESS IT ALL THE WAY UP
Have fun with your engagement session fashion! I recommend two different looks for both of you during the session. One that is more casual (think date night at a swanky rooftop bar) and one that is your “red carpet look.” Your engagement session wardrobe should be clean and minimal (avoid busy patterns like plaid). Choose classic pieces that deliver the “wow” factor, while still feeling like “you.” Keep your styling relatively timeless as these images will live with you well past the year they were taken.
Pro Tip: Coordinate your color palette across all your looks for a cohesive gallery and images that will mix and match well throughout your home.
#04 | TREAT YO’ SELF
There is no better time to pamper yourself than for your engagement session! Schedule a facial in the week leading up to your session. Book a professional hair and makeup artist. Get that mani/pedi. Wax your brows. Splurge on the shoes. Not only will this make you feel like a million bucks, but it’s a great way to discover your likes and dislikes before heading into your wedding day. You can’t buy confidence, but you can invest in things that will give you a good boost of it. And when
you’re feeling confident that translates to images you will love even more.
Pro Tip: Take your fiancé(e) with you for your mani/pedi to clean up those cuticles of theirs and spend some quality time together — your partner deserves some pampering too.
#05 | GET YOUR PETS INVOLVED
Let’s face it, your pets are your babies and they just aren’t on this earth long enough! Whether it’s a canine or feline companion, you can absolutely include them in your session. There are two ways I recommend including pets in your engagement session. The first is to do part of the session at home. This is a great way to also document your first place together, which is another great storytelling element.
The second is to recruit a friend or family member to be the “pet wrangler” at your engagement photo session. Arrange for them to join you on-location
with your pet for that segment of your session, and once the pet modeling is complete, they can safely take your pet back home. Whether at home or with a pet wrangler, you’ll be able to stay relaxed while including your (let’s be honest) favorite “person” in your session.
Pro Tip: Be sure to keep your pets on leash when on location and bring lots of treats to reward them for their excellent modeling skills.
BONUS | REMEMBER YOUR “WHY”
When you keep the love between the two of you at the forefront — and remember why you’re marrying this person in the first place — your love will inevitably shine through every image. During the session, let the rest of the world fade away and fully immerse yourself in the moment. You’ll get the most out of your time and leave feeling even more deeply in love — which is what this is all about to begin with!
Pro Tip: Take some time before the session to individually write some pre-wedding vows or love notes to each other that you can exchange during your engagement session to really help get those vibes flowing.
I hope these tips will help you not only tell your love story in an authentic and gorgeous way, but also allow you to have a blast in the process!