What to Wear for Your Engagement Session: Comfort, Confidence, and Style Tips

By My Family Treasures Photography | Proposal & Wedding Photographer in Westchester, NY

Let’s Talk Style: What to Wear and How to Prep for Your Engagement Session

You’re engaged. You’re glowing. And now you’re planning your engagement photos. But let’s be real, figuring out what to wear and how to prep can feel like a lot. As a Westchester wedding and proposal photographer, I’ve worked with so many amazing couples who felt overwhelmed at first. The good news? You don’t need to be a model or a fashion expert to look incredible in your photos.

The only real requirement: wear something you feel confident and comfortable in. The session should feel like a celebration, not a checklist. So let’s make it fun, low-stress, and fully you.

Engagement Session Styling at a Glance

• Wear what you feel amazing in
• Choose outfits that reflect your personalities and coordinate together
• Avoid loud patterns, stripes, and anything uncomfortable
• Use the session for a hair and makeup trial
• Clean your ring ahead of time
• Don’t tan
• Turn your shoot into a mini celebration

Rule #1: Confidence Over Everything

Before we talk about colors and accessories, I want to start with this: If you don’t feel good in it, don’t wear it.

The best photos come from moments when you feel relaxed, comfortable, and connected with each other. Choose outfits that make you feel like your best self. No stiff collars, itchy fabrics, or body-hugging dresses that make you want to skip dinner.

This shoot is about your love story. And you deserve to enjoy every second of it.

What to Wear (and What Not To)

Do:

• Choose clothes you feel amazing in
• Bring options if you’re unsure (one casual, one more dressy works great)
• Think about how your colors complement each other, without matching exactly
• Stick to neutral, soft, or earthy tones like tan, dusty blue, cream, olive, blush, or navy for a timeless look
• Add accessories like a cute hat, earrings, or bracelet to show off your personal style

Avoid:

• Loud patterns or logos that distract from your faces
• Neon colors or super-bright tones (they tend to reflect and cast weird glows)
• Stripes, which don’t always photograph well (same for the color red)
• Outfits that are too tight or too loose—you want something that fits just right

Bonus tip: Flowy skirts or dresses add beautiful movement to your photos, especially in natural light and outdoor settings around Westchester.

For Him: Keep It Clean and Classic

You don’t have to wear a full suit (unless you want to), but avoid super casual pieces like athletic gear or shorts. Think elevated everyday wear: dark jeans or slacks, a button-down or sweater, and a clean pair of shoes.

Match the vibe of your partner’s outfit. If she’s in a maxi dress, a tee and sneakers probably aren’t the move.

Also: take everything out of your pockets. Phones, keys, wallets… they show in photos and can’t always be edited out.

Prep Your Details: Hair, Makeup, and That Ring

Hair and Makeup Trial Run

Your engagement session is the perfect time to book your wedding hair and makeup trial. You’ll look and feel amazing, plus you’ll get to see how it photographs. Win-win. If you don’t have a trial scheduled, consider treating yourself to a little professional glow-up anyway. You deserve to feel pampered.

Clean Your Ring

I’ll definitely be getting close-up shots of your ring, so give it a good cleaning before the shoot. A simple polish or professional cleaning can bring back that sparkle you had when it first slipped on your finger.

Skip the Tan

This is a big one: please skip the spray tan or tanning bed. Even if you’re going for a golden glow, tanning can cause your skin to photograph orange, uneven, or shadowy—especially in natural light. Let your skin be its natural tone. I promise you’ll look amazing.

Make a Date of It

You’re already looking great, feeling in love, and dressed sharp. Don’t go home and change right away, but make it a full date night. Book a dinner reservation somewhere fun in Westchester (or even grab pizza at your favorite local spot). Celebrate this sweet season of your lives. You’ve earned it.

Your engagement session should be more than just photos. It’s about connection, joy, and documenting the real story of you two. Right here, right now.

Looking for more tips or help with choosing outfits? I’m always happy to guide you. Whether we’re planning a proposal shoot in the Hudson Valley or an engagement session at Untermyer Gardens, I’ve got ideas for every style.

My Family Treasures Photography

Proposal and Wedding Photographer in Westchester, New York
Where comfort meets confidence, and your story takes center stage.