There’s nothing quite as exciting as planning a wedding and scheduling in your engagement session! In this guide we will go over why engagement photos matter, when and how to schedule in your session, best Wisconsin and Chicago Engagement Photo locations, outfits, prep, tips and more! Now, let’s dive into your engagement photoshoot checklist guide!
1. Why Engagement Photos Matter
2. When to Schedule Your Session
3. How to Pick the Perfect Location
4. Best Wisconsin Engagement Photo Locations
5. Best Chicago Engagement Photo Locations
6. What to Wear for Your Engagement Photos
7. Understanding the Color Wheel & Outfit Coordination
8. Preparing for the Best Photos Ever
9. Scheduling a Hair & Makeup Trial
10. Posing Tips to Look and Feel Natural
11. Must-Have Engagement Photo Checklist
12. FAQs: Everything You Need to Know
13. Pro Tips & Unique Engagement Photo Ideas
14. Personal Stories & Client Reviews
15. About Your Photographer
So, you’re engaged? First off, congratulations!! Now, let’s talk about why engagement photos are kind of a big deal. Think of them as a test run before your wedding day. You get comfortable in front of the camera, meet with your photographer (that’s me!), and capture this special time in your life before the craziness of wedding planning takes over. Plus, these photos make for awesome save the dates! Another bonus? Engagement sessions help you learn which poses feel most natural, so by the time your wedding rolls around, you’ll be a pro.
The best time for engagement photos? Honestly, it depends on the vibe you’re going for. Want dreamy golden-hour shots with warm, glowy light? Aim for early morning or just before sunset. Love the cozy, romantic feel of fall? Book your session in September or October. Looking for a fresh, springtime feel? April and May are your best bet.
If you’re planning to use your engagement photos for save-the-dates, you’ll want to schedule your session at least 8 months before your wedding to allow for editing and printing time.
Your engagement session location should feel like you, a reflection of your relationship, style, and favorite memories together. Here’s how to find the perfect spot:
-Personalize It: Pick a place that represents your personalities, whether it’s outdoorsy, city, chic, or cozy and intimate.
-Sentimental: Think about locations that are meaningful- where you first met, had your first date, or got engaged.
-Vibes: Are you more into nature filled parks and lakes, or does a city skyline backdrop feel more like you?
-Accessibility – Choose a spot that’s easy to get to and comfortable to move around in.
-Variety – Locations with multiple settings (like a mix of greenery, architecture, and waterfront views) give more options for your photos.
-Time of Day and the Season – Golden hour (shortly after sunrise or before sunset) offers dreamy light, while seasons impact foliage and overall aesthetic.
-Crowds and Privacy – Popular spots can be busy, so consider a sunrise session if you want fewer people around.
I know all the best spots! If you’re unsure where to go, I can help you choose a location that fits your vision and ensures the best lighting, backdrop, and overall experience.
-Dress appropriately for the weather and location.
-Bring comfy shoes for walking between spots.
-Embrace the little moments—these photos are all about capturing you both authentically!
-Milwaukee Riverwalk & Third Ward
-Lincoln Park & Nature Boardwalk
Looking for more inspiration? You’ll love this Devils Lake State Park Engagement Photos Guide!
Here’s the deal: wear something that makes you feel confident and comfortable.
-Stick to neutrals or earth tones! They photograph beautifully and don’t distract from you.
-Complementary colors (like blue & orange or burgundy & forest green) look incredible together.
-Consider the location’s colors! Soft pastels for spring, warm tones for fall, cool neutrals for urban shoots.
-Avoid loud patterns or neon colors that might clash or overpower the scene.
Want more inspo? All my clients receive a in depth outfit guide and engagement session guide that’ll make planning a breeze! Get in touch through this link.
A little prep goes a long way when it comes to making your engagement session feel stress-free:
-Get your ring cleaned! Nothing like that extra sparkle in close-up shots.
-Bring comfortable shoes! If we’re hiking to a spot, you’ll want to be comfy.
-Schedule your hair and makeup trial for your engagement session! Not only will you look amazing, but it’s a great opportunity to test your wedding look!
-Hydrate and get plenty of rest! Looking fresh and energized makes a difference and when you’re hydrated, your skin loves it!
-Bring a small touch up kit: Lipstick, powder, blotting paper, and hair spray can be lifesavers.
-Not sure what to do with your hands? No worries, I got you! I’ll guide you into poses that feel candid, relaxed, and natural. But if you want a few quick tips:
-No matter what, just keep moving! Walk, spin, hug, dance, twirl, bump, jump, etc- it keeps things feeling effortless and fun.
-Lean into each other! The closer, the better. Do this however it naturally happens at home.Photographer who? Where even is she? Just focus on your partner, and I’ll handle the rest. Don’t even look at me unless I ask!
Want something different? Here are a few creative ideas:
-Seasonal Themes: Cozy fall flannels, a winter ice skating vibe, or a summer bike ride, a state fair session, or a picnic at your favorite park.
-Incorporate Your Hobbies: Love coffee? Let’s shoot at your favorite coffee shop. Obsessed with hiking? Let’s hit the trails. A bookworm? Let’s head to the library or local bookstore. A record lover? Let’s go to a record store. Love to kayak/canoe? Let’s bring your canoe! Love wine and painting? Bring a canvas and stand to a local park or invite me to your house and let’s make it happen! Homebody? On my way over for some cozy in home session vibes!
-Destination Engagement Session: Travel somewhere meaningful, like where you had your first date or explore a new city or park together.
–At-Home Cozy Session: Snuggle up with blankets, coffee, and your pup for intimate, relaxed photos.
-Pick a date and book your session
-Choose a location that fits your vibe
-Plan outfits (and try them on beforehand!)
-Schedule hair and makeup trial if you want a little extra glam
-Clean your ring for that extra sparkle
-Bring comfy shoes for walking
-Trust the process and have fun
Q: How long does an engagement session last?
A: Most sessions last about 60-90 minutes, giving us time for different poses, locations, and lighting changes.
Q: Can we bring our dog?
A: OMG YES! I love when couples bring their pups. Just bring a friend to help hold the leash when needed. This will all be dependent on location too though, because not all locations allow dogs unfortunately!
Q: What happens if it rains?
A: We can either embrace it for some dreamy, romantic rain shots or reschedule for another date. I usually shoot rain or shine. I do have clear umbrellas!!
“We love our engagement photos. Although it was a cold dreary Nov day in WI, Jessica’s editing and eye really brought us to life! She was great to work with, responsive, and sharp skilled!” -Nora and Peter
“Jessica rocked our engagement pictures! Both my fiance and I don’t love getting our pictures taken, but Jess made our session feel very relaxed and fun. She was responsive with emails and quick with getting our photos back to us, so I can now gawk at them 50 times a day!” -Briona and Noah
Hey, I’m Jessica! I’m a Wisconsin & Chicago based photographer, traveling worldwide! I specialize in capturing real and authentic moments that feel like you. I help couples create a dream engagement session that’s relaxed, fun, and stress-free, so that you walk away with photos you’ll actually love.
Want to see a Kohler Andrae State Park Engagement Session? Read through this blog and save it for later!
If you’re vibing with my style, let’s make it happen! Get in touch here.