Your engagement session is all about celebrating this sweet season in your relationship… and figuring out what to wear for your engagement photos is a big part of setting the tone. Think of it like dressing for a romantic date night or an elevated evening out: polished, effortless and you at your best.

Dress with Intention (and a little flair)

When choosing your outfits, go for pieces that feel a step above everyday but still true to your style. A good rule of thumb: if you’d wear it to your favorite upscale restaurant or cocktail bar, you’re on the right track. Well-fitting clothing always photographs best (no tugging or adjusting needed), and intentional choices can take your photos from casual to truly keepsake-worthy.

For women: Flowy dresses, midi skirts, tailored jumpsuits, or anything with a little movement and shape tends to photograph beautifully.

For men: A tailored suit, sport coat, or fitted trousers with a crisp shirt is always a win. Bonus points for layers or texture.

And remember—coordination over matching. You don’t need to wear the same colors, but your outfits should complement each other in tone and vibe.

Let’s Talk Color

Neutrals will always be in style—creamy whites, soft beiges, warm taupes, and muted grays all photograph beautifully. But if you’re wondering what to wear for your engagement photos and color is calling your name, soft and romantic tones are a dream.

Some favorites that work especially well in downtown Chicago:

• Blush, dusty rose, and pale peach
• Sage or eucalyptus green
• Powder blue or soft periwinkle
• Champagne, ivory, or light gold
• Dusty lavender or muted lilac

These shades are subtle, elegant, and have just the right amount of personality. Consider your location too—a soft blue dress near the river, sage green in a garden setting, or blush tones against the clean lines of the city can really pop in the best way.

The Little Things Make a Big Difference

Details matter, especially up close.

Hair & Makeup: If you love getting glammed up, professional hair and makeup can give you that extra boost. If not, just aim for a polished version of your usual look—whatever makes you feel your best.

Hands: Between ring shots and close-ups, your hands will get their moment. A fresh manicure—whether bold, neutral, or just clean and trimmed—goes a long way.

Accessories: A delicate necklace, statement earrings, or a favorite watch can pull your look together. One or two well-chosen pieces are usually all you need.

Confidence Is the Best Thing You Can Wear

At the end of the day, the most important thing is that you feel good in what you’re wearing. If your shoes hurt or you’re constantly adjusting your top, that discomfort will show. Choose pieces that make you feel confident, comfortable, and completely yourself. That ease and joy will come through in every single photo.

Where to Shop for Your Engagement Session

If you’re looking to add a few new pieces to your wardrobe for your engagement photos, here are some favorite brands and shops my clients (and I!) love. These are go-tos for finding elevated, romantic, and timeless pieces that photograph beautifully:

For Women:

• Ulla Johnson – Flowing silhouettes, romantic details, and always camera-ready.
• Reformation – Feminine styles with great movement, perfect for soft, natural photos.
• Doen – Ethereal, vintage-inspired pieces with a dreamy, bohemian edge.
• Anthropologie – A wide range of dresses and jumpsuits that feel unique and romantic.
• Hill House – Their nap dresses are surprisingly photogenic and oh-so-comfortable.
• Shopbop – Great for finding standout pieces from designers like Staud, ALC, and more.
• Sezane – French girl style with soft colors and pretty details.

For Men:

• Bonobos – Great fit options and polished, modern pieces.
• J.Crew – Classic style with elevated basics and great suits.
• Banana Republic – Tailored separates in timeless tones and textures.
• Suit Supply – A solid choice if you want to go full suit with a perfect fit.

Bonus tip: For couples who want to try a few looks without the commitment, consider Rent the Runway for designer pieces you can borrow just for the shoot.

Need a Little Extra Inspiration?

If you’re still piecing together your look, I’ve got you covered! You can browse my Engagement Session Wardrobe Inspo Pinterest Board for more visual ideas and outfit pairings I love. And don’t forget to check out the Artistrie Co. Engagement Session Guide for tips on locations, timing, what to bring, and how to make the most of your session. As always, if you have questions or want a second opinion on outfits, I’m just an email away!