The Engagement Session: How I Choose My Outfits

Choosing outfits for your engagement session can be tricky, because there are several things to think about at once. The main factors to consider are fit, color, and style.

In this post, I'll walk through our last few photo sessions as case studies and explain my thought process in choosing our outfits.

Caitlin + Ryan - October 2013-0082_WEB.jpg

We did anniversary photos in 2013 with our friend Chelsea, who is famous for her black and white images. So I put a lot of thought into how our outfits would complement but still contrast both in color and in black and white.

After looking through my closet, I knew that I didn't have the right piece for our session, so I went shopping. I was really happy to find this navy dress, because it fits me really well. Fit is so important, because I knew I didn't want to be constantly adjusting my clothing throughout the session and the dress draped in a really flattering way. 

Ryan and I chose his shirt to complement my navy dress, since it was the same color but a different shade. I tell my clients to steer clear of prints that are either really tiny or really big, but most plaid shirts like this one are perfect for adding a little pattern interest.

And then I added the green cardigan to keep it from being too much blue. Complementary colors! The cardigan also gives the session more of a fall feel (because fall is my favorite), and it's flattering on my arms. And if a little sweater means that I won't have to look at a photo and say "my arms look terrible", then bring on the sweaters!

See how my dress and his pants are the darks, my sweater is a mid-tone gray, and his shirt is a light tone? That's tricky to see when you're looking at colorful outfits, but when you nail it, it's awesome!

A quick tip for figuring this out at home... lay out your clothing together as if you were wearing it (wrap your cardigan around your dress and layer your jewelry on top). Then take a photo with your phone and change it to black and white. (I recommend taking down the saturation completely instead of using a filter so the color tones aren't distorted.) This will show you if you have a good balance of lights, mid-tones, and darks or if your color tones are blending into each other too much.

(Photo credit: Bit of Ivory Photography)

Easter Photos-103_WEB.jpg

In 2015, Ryan and I had a few portraits taken at Easter. (Hello, bangs!) And while I was picking out the outfit based on what I wanted to wear for church, I also thought about what would look good for pictures at the park.

I love this little black lace dress, because it can be dressed up or down, but the lace doesn't show up well on camera, so I added the cardigan and scarf for some texture and color. Also, because my hair is really dark, I didn't want it to blend in with my dress. (This would even be a problem in color photos, so it's definitely something to consider for those with dark hair.)

Ryan asked what he should wear and I suggested a light blue dress shirt to match the pastel Easter tone of my sweater. (Again, complementary colors!) And layering the gray sweater gives the black and white image a nice mid-tone.

And again, I didn't want any clothing that would bunch or pull or need adjusting during the session, so I chose a scarf instead of a belt, since the dress doesn't have loops to hold it in place.

If I had one criticism for this outfit, it would be that the bottom of my dress blends in to his black jeans a bit. That might sound a little nit-picky, and in this case, our main goal was to have an updated photo for my blog and profile photos, I wasn't as concerned about the bottom half of our outfits.

(Photo credit: Andrew and Tianna)


In 2016, we had another session with Chelsea for updated anniversary photos that we could also use as headshots and branding photos here on my website. Because the photos were for branding, my dress had to be purple. I also wanted something long (for formality) and flowy (for movement in photos). And I wanted sleeves (again... to flatter my arms). After looking just about everywhere for a long flowy purple dress with sleeves, I found my dream dress in the perfect eggplant shade. (It's actually a maternity style from Sew Trendy Accessories.) We wanted Ryan to look sharp and masculine so we bought him a new gray suit in a slim fit style.

(Photo credit: Bit of Ivory Photography)

I also wanted to mention our height difference. Ryan is 11 inches taller than me. Take a moment to scroll back through the photos and see how short I look. I'm even wearing heels in some of the photos. And that's ok! This is who Ryan and I are! So embrace the way you guys fit together, whether that means you barely reach the top of his shoulder or you two can stand eye to eye.

Back Bay -0055a.jpg

Finding a dress for our maternity session was hard! I knew none of the dresses I had were quite right. My favorite maternity dress was purple, but I was determined to make this session look completely different from our headshots. I ended up borrowing this white dress from a friend. Adding a belt over the cardigan helped to keep the waistline defined (extra important for maternity photos). We knew blue and white would be great colors for the beach, so we chose navy and gray for Ryan to keep in those color families without being too matchy matchy.

And one more quick note... I had my makeup done for all three of these sessions (not the Easter photos) and it makes all the difference! I feel my most beautiful when someone who knows what they're doing applies my makeup, and my eyes really pop on camera with fake eyelashes! Professional makeup for each of our photos sessions is so important to me that I paid for it 4 times in 2016! (It was a heavily photographed year!)

(Photo credit: Lauren Simmons)

I hope this helps you think through the fit, color, and style of your clothing when you're choosing engagement session outfits. Because the right outfit makes all the difference!


Want to read more tips for your engagement session?
Choosing a Location
My Favorite Hampton Roads Locations
What To Wear
What Not to Wear
What Happens if it Rains
The Engagement Guest Book
Engagement Session Posing
The Purpose
Getting to Know Your Photographer
How I Chose My Outfits
10 Final Tips