5 Tips for Your Engagement Session

 

A couple of years ago, I was photographing a sweet couple’s engagement session when, as I leaned in to capture a close-up of her gorgeous ring (a beautiful symbol of forever love), she suddenly pulled her hand off his shoulder. “Oh,” she said, “I totally spaced doing my nails. I’m so sorry.”

On the drive home, I couldn’t stop thinking about her apology. Why had she felt the need to say sorry? Then it hit me—I had never communicated to her that I’d be taking close-up shots of her ring. That moment was a huge learning experience for me. I realized that helping couples prepare for their engagement session is as important as showing up with my camera.

Since then, I’ve refined my approach to engagement sessions, keeping an eye on all the little details that make the experience feel effortless and special. Over the years, I’ve pinpointed five key tips that can elevate your engagement photos and make them even more memorable.

(Wondering where to take your photos? Check out my recommendations for the best Chicago engagement photo locations or my favorite spots for destination and northern Michigan sessions.)

1. Make a special evening out of it!

Your engagement session isn’t just about the photos—it’s an opportunity to celebrate your love story. I like to limit wedding-related talk during our time together so the focus stays on your relationship.

To make the day even more special, consider taking the day off work. Use the extra time to prepare together stress-free, enjoy the process of getting ready, and soak in the excitement.

After the session, I recommend making dinner reservations at one of your favorite restaurants (or somewhere you’ve been wanting to try!). You’ll already be dressed up, feeling fabulous, and it’s a perfect excuse to enjoy some uninterrupted time together—no wedding talk allowed!

5 Tips for Engagement Session Erika Aileen Photography

2. Get your hair and makeup done.

Having your hair and makeup professionally done isn’t just a luxury—it’s a game-changer for engagement photos. A professional will ensure your makeup translates beautifully on camera, enhancing your natural features and giving you a polished look.

Plus, it’s one less thing for you to stress about on the day of your session. Many of my Chicago and destination brides use their engagement session as a makeup trial with their wedding artist. It’s a great way to test your look while getting stunning photos at the same time.

tips for your engagement photos erika aileen photography

3. what to wear For your Engagement session

Not long ago, my husband and I had our anniversary photos taken, and I spent hours agonizing over what to wear. Between scrolling Nordstrom and Rent the Runway, I learned so much about choosing outfits that not only photograph beautifully but also make you feel amazing.

If you’re feeling overwhelmed, consider connecting with a bridal stylist (Gabbi is an incredible resource!) to help curate your look. But above all, wear something that makes you feel confident. When you feel good, that energy shines through in your photos.

For more detailed guidance, I’ve written a two-part series on what to wear for your engagement session part I and part II linked!

chicago sailboat engagement session tips for your engagement photos erika aileen photography

4. Pay attention to your nails!

As I mentioned earlier, your engagement session is a perfect time to pamper yourself with a manicure. Whether you prefer a classic neutral, a bold color to match your outfit, or just a simple swipe of clear polish, tidy nails make your beautiful ring pop even more in close-up shots.

If you’re not one for manicures, don’t stress—a quick file and clear coat will work wonders and still keep the focus on your ring!

downtown chicago engagement photos tips for your engagement photos erika aileen photography

5. Make sure you’re on time.

This might be the most important tip of all! I prefer to shoot engagement sessions in natural light, which means we’re working with the sun’s schedule. If you’re late, we lose precious minutes of golden-hour glow that we can’t get back. Being on time ensures we have the full session to relax, explore your location, and capture every shot without rushing. Trust me, starting off on the right foot makes all the difference in your experience.

Engagement photos are more than just a prelude to your wedding day—they’re an opportunity to capture your unique love story. Whether you’re strolling through the iconic streets of Chicago, exploring the scenic beauty of northern Michigan, or planning a destination session in a far-off romantic locale, a little preparation goes a long way in making the experience unforgettable.

Are you dreaming of a luxury engagement session or wedding? I specialize in capturing timeless love stories in Chicago, northern Michigan, and destinations worldwide. Let’s connect to bring your vision to life!

Click below to peruse some of my favorite engagement sessions:
Lake Michigan Sailboat Photos
Brooklyn Bridge & DUMBO Engagement Photos
Romantic Beachside Engagement Photos