What to Wear to Your Engagement Session

2025 Florida- Anna So Photography

What Should I Wear to My Engagement Session?

Each year, Blake and I take anniversary photos together. It’s something I’ve come to really love. It’s a chance to explore a new location, get in front of the camera instead of behind it, and honestly… learn from other photographers in a unique way. : )

But I’ll be real with you… choosing outfits? It can feel like a lot.

Even as a photographer, I’ve found myself standing in front of the closet thinking, “Wait… what actually photographs well?”

So I sat down and thought through how I approach choosing our outfits each year (Blake trusts the process.), and I wanted to share a few things that have made the biggest difference for us.

Start with What Feels Like You

Before we get into colors or styles, this matters most:

Wear something you feel comfortable and confident in.

If you’re adjusting your outfit, second guessing it, or feeling unlike yourself, that will show up in your photos. But when you feel good? Everything softens. You relax. You have fun. And that’s when the magic happens.

2025 Florida- Anna So Photography

Coordinate, Don’t Match

This is a big one.

Instead of trying to wear the exact same colors, think about how your outfits can complement each other.

Choose a color palette that works well together rather than identical pieces. Soft neutrals, mixed textures, or one patterned piece paired with something simple always photograph beautifully.

Think of your outfits as telling the same story, just in different voices.

Here are a few of our favorites from over the years. : )

The Lees || Sara Bishop Photography || Cassie Lacina
Kim Ritchie Photography || Cassie Lacina || Kathryn Faye Photography

Two Outfits = More Variety

I always recommend bringing two outfits for your engagement session:

• One dressy or more elevated
• One casual or relaxed

This gives you two completely different looks in your final gallery and adds so much variety to your photos.

We’ll typically start with the dressier option and then transition into something more casual halfway through.

These are some oldies, but still some of my favorite shots.

2018 Cliffs of California- The Lees

Sherah Grose Photography- 2020 Wheaton… That beard!

Neutrals vs. Bold Colors

If you love that light, soft, romantic look, neutrals are always a beautiful choice.

Think:

• Creams, whites, tans
• Blush, light pinks
• Soft blues or muted tones

These colors photograph bright, airy, and timeless.

That said… a bold pop of color can be so fun when done well.

If you go bold, I recommend:

• One person wears the statement piece
• The other stays more neutral to balance it out 

The Orange Pants

While Blake and I typically trend toward neutrals, blues and greens, we both went through an orange pants phase at different times. A bold look, balanced with neutrals. : )

2023 Arizona- Sara Bishop Photography || 2026 Missouri- Kathryn Faye Photography

A Few Things to Avoid

There are no strict rules, but here are a few things that tend to photograph less beautifully:

• Bright reds and neons, especially as tops (they can reflect onto skin tones)
• Small, busy patterns
• Large logos or graphic tees
• Athletic shoes (in most cases)
• One outfit being very dressy while the other is super casual

When in doubt, simpler is usually better.

Final Thoughts

At the end of the day, your engagement session isn’t about the outfits.

It’s about the two of you, your connection, and this really sweet season of life you’re in. : )

Choose pieces you love. Trust your instincts and I can’t WAIT to see what you land on!

Much Love,