10 Tips For Choosing Engagement Session Outfits


Today’s blog post is all about giving some inspiration and ideas to all my current (and future) Comfort and Cashmere brides as they prepare to choose engagement session outfits. I remember when I was planning my engagement pictures that it took me quite awhile to figure out what I wanted for our outfits, so I am SO excited to share some tips and inspiration ideas! 

photos showing two different engagement outfits a couple is wearing. dressy and then casual

  1. Two outfits are better than one! Many of my couples will choose two outfits for their engagement sessions—one dressy and one casual and relaxed. Two engagement session outfits is a perfect number, in my opinion, because it will allow for a wide variety in your portraits.
  2. Coordinating, not matching! Try to coordinate your outfits instead of matching them. Wearing the same color in different shades is more ideal than matching the exact color. A great example would be avoiding both wearing navy tops with khaki bottoms because it comes across like you’re wearing uniforms. 
  3. Coordinate a patterned outfit with a neutral tone! If both of you wear patterns, you tend to disappear into the fabric and become floating heads, but if one of you wears a neutral, solid tone, the pattern enhances rather than overwhelms.
  4. Big patterns are better than little! When wearing a pattern, go with the larger style pattern instead of a smaller one. Rock a large print plaid! Buffalo plaid steals my heart every time! A large print photographs better than a tiny pattern as the camera doesn’t always pick up on the tiny patterns from far away. 
  5. Add a splash of your wedding colors to your engagement outfits! There’s a trend right now where couples coordinate their outfits with their wedding day theme or incorporate a color or texture into their attire from their Save The Dates. It looks really sharp!
  6. Simplicity is also fantastic! If you start to feel overwhelmed, take a breath and remember that simple is perfect too. Some of my most favorite engagement sessions have the groom rocking a solid colored V-neck. 
  7. Formal vs Casual! If a bride-to-be wants to wear a gorgeous navy gown, then the groom should probably not wear jeans and a basic T-shirt. Just make sure to be equal in how formal or casual your attire is. 
  8. Be you, Boo! Use your outfits to show off your unique personalities and style. 
  9. Utilize accessories! Necklaces, earrings, belts, scarves…they are all great for engagement session outfits! They add fun aspects to each outfit and it’ll give you something to hold onto in photos if you don’t have long hair. 
  10. Flatter your figure and skin tone! I saved the best for last! Even though there are more tips in the bridal guide I give to all my Comfort & Cashmere Brides. I highly recommend paying attention to wearing engagement outfits that flatter your figure and skin tone. I know it seems like common sense, but I’ve personally made the mistake of thinking a color looks amazing with my skin tone and then seeing a photo and looking green. Everyone has certain colors, tones, and textures that look amazing on them and certain things that aren’t made for me them. Put your outfit on and have someone take a pic. If the outfit makes you look washed out or muted or if it turns your skin a different tone, it’s not the right outfit! I love that mustard color, but since I have a more olive skin tone, it just brings out green shades, so I know not to photograph in mustard. 

40-something man and women walk along a snow-covered bridge, hand in hand, then stop for a kiss beside the ocean

young couple poses for photos showing two different engagement outfits, one long black dress and pink shirt and jeans, the other a red sweater for her and a cream sweater for him

a couple walks along the beach, he is wearing a white t-shirt and jeans, she is wearing jeans, a white shirt and a turquoise sweater. They are smiling and laughing showing off their engagement outfits. Photos by Comfort and Cashmere

The bottom line is to make sure you’re wearing clothing that makes you feel beautiful, confident, and comfortable. I’ll teach you how to pose in flattering ways, but you’ll fall in love with your images over and over again if you wear outfits that you’re comfortable and confident in. 

I can’t wait to work with you!  

Here are some more ideas about choosing engagement outfits and make sure you read through these other engagement tips about announcing your engagement on social media and how to start planning your wedding!


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Fueled by equal parts strong coffee and French 75’s, I spend my days capturing the kinds of images that convey distinctive emotion through intentional moments and create elevated images you’ll treasure for a lifetime. I showcase your story and your love in an exceptional, gracious way. I believe in real moments, heartfelt conversations, love stories that grow stronger through the storms and the kind of joy that can be found in the simplest of moments together. When I'm not tearing up during the vows, you'll find me whipping up a new recipe in the kitchen, listening to Sinatra, or snuggling with my mini me.

I’m Rohana Olson

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