What to Wear to Your Portrait Session | Outfit Ideas and Styling Tips from a Boston Lifestyle Photographer

Choosing what to wear to your portrait session can be overwhelming. Whether that is your Boston engagement photos, family lifestyle photography session, or an in-home newborn photography session, there is a lot to consider.

While I’m not nearly as picky as some photographers can be, I do have a few preferences and suggestions for what to wear to your portrait session to make your photos look the best they can! Below, I list out a few dos and don’ts for you along with some assistance with how best to coordinate clothes and choose appropriate outfits based on the season. Hopefully this will eliminate some of that stress and help you to choose outfits that will look amazing in your photos.

What NOT to wear to your portrait session…

When deciding on what to wear to your portrait session, you want the focus to be on your faces, not on distracting clothing items. Here are some common clothing items to avoid:

• Clothing with large logos, pictures, or characters

• Flip flops

• Outfits that show bra straps or undergarments

• Hoodies

• Neon colors

• Transitional Lenses - if you typically wear glasses, wear them for your session. But if you have transitional lenses, consider taking them off. Dark glasses will cover your eyes in the photos.

• Short dresses & skirts – for maximum comfort over any other reason. Short skirts can make it difficult to comfortably pose, sit, and play. If you’re not sure if your skirt is long enough, test it out by seeing if you can sit and walk without having to adjust.

• Identical clothing – for example, everybody in the family wears jeans and white tops. When everybody matches, your photos will look very staged and posed. It will be obvious that you were dressing for a photo shoot. While I am not trying to hide the fact that you are participating in a photo shoot, the photos will turn out better of you are wearing coordinating but not matching outfits. More on that to follow…

How do I coordinate clothes for my portrait session? What colors should I wear?

Coordination can be a tricky balancing act. You don’t want everyone to wear the exact same thing, but the colors and styles should blend well together. My best advice is to start with one member of the family (or couple). Have that person choose an outfit that they love and feel great in. Pull colors from their outfit to dress everyone else. Stick with 2-3 colors from that first outfit and stick to those shades coordinated with neutrals as your palette. If you are buying new clothes, choose a palette to begin with. For example pastels (pinks and blues), primary colors (red and blue), earth tones (navy, tan, burgundy, or green) etc. (see one great example from this Boston engagement session). Find an outfit for each family member that has at least one predominant color in the palette and balance that with neutrals like tans, greys & cream. Once you think you have everyone’s outfits picked out, lay them out together and see if they look good! If not, replace whatever clashes.

Style by session type and season.

What to wear for your family lifestyle session or engagement session:

For both of these types of photo sessions, you should focus on coordinating complimentary colors with neutrals and choosing an in-season wardrobe. As you know, the weather during your Boston portrait session can vary greatly depending on the season. When in doubt, wear layers. For spring sessions, you may want to work in some pastels or florals to match your environment. For a fall session, consider jewel tones. You might select certain colors and style based on when you plan to share the images. A family holiday card, for example might call for different color choices than an engagement session for your beach wedding save the dates. As always, avoid large logos, clashing patterns, and neon colors.

What to wear for your senior session:

This session is all about celebrating you and your momentous occasion. Let your personal style shine! You can dress up or dress casually, but make sure that your style is at the peak of its game. Wear the very best outfit you have to show your personality - not necessarily just what you would wear every day.

What to wear for your maternity session:

Maternity photos are another case where you will want your personal style to shine, as well as your shape. Choose a dress or a shirt that will accentuate and show off your bump - that is the point of these photos after all! Prioritize your comfort and how beautiful you feel in your outfit over anything else.

What to wear for your in-home newborn session or in-home family session:

Think cozy but not TOO cozy. Keep your clothing neutral, soft, and comfortable but refrain from actually wearing pajamas (unless of course that’s the theme you’re going for). Babies can wear minimal clothing. Diaper covers, neutral-colored onesies and swaddle blankets are perfect.

The most important tip for what to wear to your portrait session: wear clothes you feel good in.

This is the most important tip! Wear what makes you feel good. While it’s important to put thought into what to wear for your portrait session, what matters most is creating an heirloom that your family will cherish for generations. You will never remember that you chose the grey shirt over the green. In the end, you’ll see past the clothing to your family laughing and holding each other close. 

Dana, Dave, & Caleb Family Session - Smith College, Northampton, MA

Dana and Dave reached out to me about getting some family photos while they were visiting home (Western Massachusetts) for the holidays. Smith College in Northampton is Dana’s alma mater and also the location that Dana and Dave chose to take engagement photos, so it made for a special setting to take some family photos with their 2 and 1/2 year old son, Caleb. We started off near the greenhouse and arboretum and made our way down the dirt path by Paradise Pond, ending up on the bench swing overlooking the pond.

Caleb was a little bit shy and preferred staying close to mom and dad, but that was no problem as it helped them to be a part of almost every photo. It was also very cold out so we kept it moving constantly. Thanks to some creativity on Dana and Dave’s part, they discovered that the phrase, “It’s chilly willy bing bong cold!” made Caleb crack up, and so of course, I had them repeat that for the remainder of the session to get some natural smiles and laughter (big shout out to Richard Wylde for the magic phrase!).

It was so much fun spending some time with this awesome family - maybe next time we’ll try meeting up in some less chilly willy bing bong cold weather? Warm sun and green grass sound pretty great to me right now.

Andi & Warren Newborn Lifestyle Session

Meet Andi & Warren! After spending two weeks in the NICU, these preemie twins made their way home healthy and we did an in home newborn lifestyle session when they were around 2 months old.

On the day of our shoot, Andi & Warren took turns falling asleep and being alert and giving me (and mom and dad) beautiful baby eye contact. I love that we were able to incorporate photos of them with their parents too. Check out a recap of our time together below!

Also, see my helpful blog post on what to wear to your portrait session if you’re planning an in-home newborn session.

Lindy and Willie's Newborn Session (Skyler)

Lindy & Willie live in the same town as me so photo sessions are super easy and fun with them. They always have new restaurant or running route recommendations for me as a relative newbie in town (Lindy grew up here). Skyler was born in late May and she was exactly 3 weeks old for our photo session. Despite a few tears at the beginning, she was just as photogenic as her parents and she worked a handful of excellent outfits styled by her mother. Lindy’s best friend happened to be there for a visit so we incorporated her into a few shots. Willie required a few photos with Skyler wrapped in a scarf from his favorite football (soccer) team, Everton F.C. She is obviously already a huge fan! Welcome to the world, Skyler!

Lindy and Willie's Maternity Session (feat. Summer the Puppy)

Lindy and Willie have a lot going on in their lives right now! They welcomed a new puppy named Summer into their family and are about to welcome a baby in May. For their maternity session, we started on their front steps and took Summer for a walk through the neighborhood and into Rye Town Park. She caused some mayhem (Lindy’s earrings were a VERY tempting toy) and wasn’t always the most focused model, but she was a wholesome, adorable, addition to this maternity session. My favorite part of the session was when we were down on the dog section of the beach. All the dogs wanted to be Summer’s best friend, and when Summer wasn’t saying hello to them, she was trying to see how big a hole she could dig in the sand. We did get some great non-blooper-reel photos in the fleeting moments of calm and focus and it was 100% worth it to have her there. I highly recommend incorporating your fur babies in photo sessions if you don’t mind things potentially going a bit haywire. Overall, such a fun day and I can’t wait to meet baby soon!

Lela and Paul's Newborn Session (Otis)

After photographing their engagement session and maternity photos, Lela and Paul asked me to do an in-home newborn session once Lela gave birth back in January. This was my first ever newborn session and I fell in love with it immediately. So many squishy details and adorable, cozy, photo ops. I wanted to incorporate mom & dad in some photos too as well as their home and space - we opened up the curtains and let lots of natural light in which made for the beautiful silhouetted family portrait you’ll see at the end. Welcome to the world, Otis!