Preparing for Your Portraits: What to Wear

From the Experts

Hands down, one of the questions I get asked the most often is “What should we wear?” Finding something perfect for yourself is hard enough, let alone coordinating with your love. When Kevin & I were preparing for our first ever portrait session I wound up laying out matching outfits at one point! That’s a serious no in the What to Wear department, so believe me when I say, I get it. As hard as it might feel, and as much as you may just want to toss on your favorite fitted tee and call it done, I promise it’s worth going the extra step.

I’m going to make it a million times easier right now by excluding the majority of options and giving you one specific recipe. Think of how easy it is to order at a restaurant that has one page of options instead of 4 and let’s do the same thing with your closet (or your favorite boutique because this is obviously the perfect occasion to splurge a bit).

The Perfect What to Wear Solution:
Ladies = Cocktail dress & stunning heels
Gentlemen = A casual suit & spiffy shoes

There are a variety of reasons this is the ideal outfit recipe, and we’ll hit upon them all in the below post but here’s Cliff’s Notes version:

  1. Both of these clothing choices tend to be fitted and flattering to numerous body types.
  2. Additionally, both of these choices work for all couples regardless of sexual orientation.
  3. It makes it simple to coordinate without matching (you love each other, you are not twins!).
  4. This is a special time. Make yourself feel special by what you choose to wear!

Here’s the beautiful thing about dressing things up. You look good wherever you are! Going for a stroll through your favorite park? Perfect. Hanging out under the romantic streetlights at night? Ideal. Dressy looks good even in the most casual of natural settings so you really can’t go wrong. Now, of course, you should use this recipe as a foundation to enhance your own personal style because the golden rule for everything is to be authentic to yourself, so I’ve picked a few of my favorite recipe versions from our real couples to help as examples.

Jessica & Jeremy nailed the recipe perfectly! They obviously don’t match but they most definitely look like they belong together. Jessica’s textured white dress had a flattering fitted waistline and her burgundy suede heels brought in a rockin’ 2nd texture. Pairing jeans with his suit coat allowed Jeremy to feel more comfortable and less like he was on his way to work.



Amy & Jon took a more casual approach to the recipe. Amy’s lace sundress is another example of great texture and the vibrant pink sets the two of them apart from the green of the Chicago Botanical Gardens perfectly. While Jon’s look is a bit more casual, it’s no less put together. His well ironed shorts and clever shoes are perfect for a warm summer day where a full suit jacket would have been too hot for the weather. Together, these two look ready to enjoy a dinner reservation al fresco.


As mentioned, you want to look like you belong together without looking like your mom put you in matching outfits. Kristen & Nancia rocked this with each of their personality-suited cocktail dresses. They clearly look ready for a special date night at the newest hot spot in New Orleans (which they promptly hit up after their engagement session!). They also followed the bonus rule on jazzing things up with their accessories as well – more to come on that later.

While solid colors are a no-fail choice, there is no reason you can’t rock patterns for your photos! Nora & Austin perfected mixing patterns together for their Garfield Park Conservatory portrait session. What makes their mixed patterns work so well is that Austin’s polka-dot shirt is a very small and subtle pattern as compared to Nora’s dress. The other key with patterns is to stick within the same color family for both outfits. As seen here, they both chose an organic neutral tone palette with similar vibrancy. Think of pairing blues, greens and browns together or grays, blacks and purples. Using accessories to coordinate each other’s color choices is another great option. See how Austin’s maroon tie plays off the pink hues in Nora’s dress?



Gregory & Jonathan’s Destination Anniversary Session is a great example of sticking with the dressy recipe yet also staying true to their surroundings. Cuffing their dress pants and donning flip-flops was the perfect touch of fun for their tropical session.


If dressy absolutely is not your thing, don’t worry. I will never ask you to force yourself into a little cocktail number if you hate it. The reason the cocktail dress + casual suit recipe works so well is that more often than not, both options are fitted. Fitted is the key to all of it. Take Lauren & Zach’s cozy fall outfits for example. There is no hiding those gorgeous fall leaves, so a cocktail dress without at least tights would have been a bit too chilly. Lauren’s sweater kept her warm while her dark jeans and heeled booties kept her look flattering. The elbow details on Zach’s shirt and vest added great details to a comfortable look and Lauren’s patterned scarf was a great addition to their solid color choices.



Getting the main pieces of your outfit choices lined up is what is most important, but when you are ready, you can really ramp up your look to the next level by considering the details. Emily & Devin coordinated their looks by matching the style of their details (Emily’s stacked bracelets and belt along with Devin’s belt and watch). While you wouldn’t usually think to pick the exact opposite color of jewelry as to your clothes, Michelle pulled it off perfectly by matching her statement earrings to her stacked bracelets. This mix of colors worked great for her and Ryan because they were each wearing solid neutral tops.


And the shoes… Always, always think about the shoes! While Marilyn Monroe stated it for the ladies, I think it’s true for anyone: “Give a girl the right shoes and she can conquer the world.”


The Cheat Sheet

  1. Cocktail dress + casual suit = Perfection!
  2. Fitted, fitted, fitted. This does not mean skin tight, but be sure to give yourself a waistline. Men and ladies alike!
  3. Dress weather appropriate. You aren’t ever going to look comfortable if you can’t feel your toes in the winter (But don’t forget #2. Make sure your coat has a belt so you aren’t adding layers of yourself that don’t actually exist!)
  4. Don’t forget the details! For ladies, it can be as simple as a stunning pair of heels and one fun accessory. For the guys, fabulous shoes (with good socks!) and one great accessory.
  5. Taking it up a level think about great belts, statement earrings or patterned socks. Jewelry is the easiest way to update your look while remaining timeless and vibrant scarves are the fashion solution to chilly days.
  6. Last but most likely the easiest, ask yourself this one question: What is the outfit I check myself out in the most? You know you have one. We all do (Click here to see mine. Those photos are from almost 5 years ago and I still wear that outfit!). When you are walking down the sidewalk and you slow down just a little bit to check yourself out in the reflection of the window, whatever you are wearing in that moment most likely is the perfect outfit to wear.

Looking for more tips & tricks? Be sure to check out the Inside Scoop section of the blog for all of our insider secrets!



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