Choosing The Perfect Outfits For Your Engagement Session

Engagement photos are more than just pictures—they’re a celebration of your love and a sneak peek into your wedding story. And let’s be real: they’re also the perfect excuse to wear something fabulous and create a few frame-worthy moments. But when it comes to choosing outfits, it’s easy to get stuck in the “what do I even wear?!” spiral.

Don’t worry, though—I’ve got your back. Whether you’re dreaming of a classic, elegant vibe or something a little more playful and fun, the perfect outfit is all about balancing your personal style with a few practical tips for how things will look on camera. Let’s dive into everything you need to know to feel amazing and look picture-perfect for your engagement session.


 

1. Stay True to You—But Don’t Be Afraid to Shine

When it comes to your engagement photo outfits, the key is finding the sweet spot between you and “wow, is that really us?” Think of it like this: your outfits should reflect your personalities and the way you normally look together, but this is also the perfect excuse to step it up a notch.

Are you a jeans-and-T-shirt kind of couple? Great—lean into that laid-back vibe, but consider elevating it with a polished button-down, a flowy blouse, or even swapping the sneakers for stylish boots. Love bold patterns and colors? Amazing! Just be mindful of how they’ll photograph and try to balance them with more neutral pieces.

And if you’re feeling adventurous, this is your chance to push the boundaries. Always dreamed of rocking a stunning gown or a tailored suit? Go for it! Want to embrace a chic, editorial vibe you wouldn’t normally wear? Absolutely! Think of it as the ultimate mix of comfort and confidence—wearing something that feels like you, but a version of you that’s ready to steal the spotlight.

 
 
a couple kneeling with their dog at their engagement photoshoot with casual outfits on

Lauren and Ken are nailing the casual look, effortlessly elevated with stylish shoes and perfectly polished hairstyles.

a couple in downtown chicago posing for their engagement photos dressed in white silk and black fitted suit

On the flip side, Liz and Marty are dressed to the nines, giving a glamorous preview of the elegance their ornate wedding will bring.

 

 

2. Dress for the Scene, Not Just the Selfies

Your engagement photo location is more than just a pretty background—it’s a character in your story. So, when you’re choosing outfits, think about how they’ll vibe with the setting. Are you hitting up a sun-soaked beach? A charming city street? Or maybe a lush, wooded park?

For outdoor shoots, soft tones and flowy fabrics can create a romantic, effortless look. In a cityscape, bolder colors or sharp silhouettes will stand out beautifully against the urban lines. Planning something cozy at home? Lean into comfy textures like knits or linen to make it feel personal and relaxed.

And here’s the golden rule: let your location shine, but don’t let it steal the show. Avoid anything that could compete too much with your surroundings—like neon brights in a forest or clashing patterns against a brick wall. Instead, think of your outfits as the perfect complement to the scene. It’s all about creating a cohesive story that feels like you.

 
 
Chicago Athletic Club Engagement photoshoot of a couple cuddled on the couch looking elegant and timeless

Paige and Adam bring their A-game with semi-formal, polished outfits that perfectly match the sophisticated charm of the Chicago Athletic Club.

 
 
LGBTQ couple at Loveland Pass, Colorado holding hands for their photo session with Ben Ramos Photography

Ally and Tessa keep it neutral and casual, perfectly complementing the epic backdrop of Loveland Pass’s stunning mountains.

 
 
luxury engagement photo session of a couple in lincoln park chicago, holding hands while crossing the street

Dyna and John are serving timeless elegance as they stroll through the chic streets of Chicago’s luxurious Lincoln Park neighborhood

 

date night vibes of a couple under the train in chicago for their BRP engagement session

Haleigh & Steve nail the classic city date night look, blending casual charm with just the right touch of sophistication.

3. Think Timeless, Not Trendy

Engagement photos are more than just pictures for save-the-dates or Instagram—they’re keepsakes you’ll cherish forever. That’s why it’s smart to aim for outfits that feel timeless rather than chasing the latest trends.

Sure, that neon jumpsuit or oversized blazer might be hot right now, but will it still feel like you in ten years? Instead, go for looks that reflect your personal style but also have a classic appeal. Think solid colors, clean lines, and pieces that won’t make you cringe when you look back on them in your wedding album.

This doesn’t mean you have to ditch all personality—far from it! Add subtle touches that are uniquely yours, like a favorite accessory, a pop of color, or shoes that make you feel like a rockstar. It’s about finding that balance between “wow, we look amazing” and “wow, we’ll always look amazing.”


Chloe and Evan nailed it by coordinating without matching, choosing outfits that made them feel amazing, and perfectly complementing their session’s setting.

4. Be Comfortable, Be Confident

Here’s the deal: no matter how stunning your outfit is, if you’re not comfortable in it, it’s going to show in the photos. The key to looking and feeling amazing is wearing something that makes you feel like the best version of yourself—not someone you barely recognize.

If you’re constantly adjusting a too-tight dress, worried about a shirt that wrinkles easily, or teetering on heels you wouldn’t normally wear, it’ll be hard to relax and enjoy the session. Instead, opt for outfits that fit well, move easily, and make you feel confident. Think breathable fabrics, shoes you can walk in, and cuts that flatter without restricting.

Confidence is your best accessory, and it starts with feeling comfortable. When you’re at ease, your photos will radiate natural joy, making every shot frame-worthy.

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Final thoughts…

At the end of the day, the perfect outfit for your engagement photos is the one that makes you feel confident, comfortable, and completely you. Whether you’re dressing up, keeping it casual, or experimenting with something new, your style should reflect your story as a couple.

Remember, these photos aren’t just about what you wear—they’re about capturing your connection and celebrating this special time in your lives. So, have fun with it, trust your photographer (hi, that’s me!), and know that no matter what you choose, you’ll look amazing.


Want to see more style inspiration from some of our other sessions? Click below to browse more engagement photos!

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Mykel & Tommy | Lake Michigan Engagement at Burnham Park

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Mitchell & Michael | Chicago, Illinois Wedding