What To Wear To Your Massachusetts Engagement Session

If you're anything like most couples, one of the very first questions that pops into your head after booking your photographer is: "What should we wear?!?"

Planning outfits for your Massachusetts engagement session can feel surprisingly overwhelming (especially when you start scrolling through Pinterest), but it doesn't have to be.

Your engagement photos should reflect you. So as a Massachusetts engagement photographer, I want you to wear what you feel good in and most like yourself in. And while there's no one-size-fits-all formula, there are some general guidelines to help make the most of your session.

So let's break down my best tips for choosing outfits that make the most sense for you 👇

Start Here: What Do You Like To Wear?

Before we talk colors and fabrics, here's the most important thing to keep in mind:

If your outfit makes you feel stiff, self-conscious, or like you're wearing a costume, it's not the right choice.

Your engagement session is about capturing who you are together. Not dressing like a version of yourselves you think you're "supposed" to be for your photos.

When couples ask me what to wear for their Massachusetts engagemnet session, the first things I always remind them are:

• Choose colors that complement your skin tones

• Plan for two outfits if possible (one casual, and one a little more elevated)

• Wear things you can move in comfortably

If you stick to these general tips, you're already off to a great start.

Think About Movement

One of the biggest outfit mistakes I see actually has nothing to do with color or style — it's forgetting to think about what we'll be doing during your session.

Ask yourself:

• Do you want playful movement or piggyback rides?

• Do you want twirls and flowy motion?

• Will you be walking around Boston neighborhoods or trails?

• Are you hoping for romantic, cozy photos?

If you're wanting a lot of playful movement, running around, and just being plain silly with your partner, you want to think about things like wearing pants, skipping heels, etc. to make sure your outfit supports the experience you're looking for. And if you want something more romantic like a cute little picnic or a stroll through the city, a flowy dress or layers work well.

Choosing Your Outfits Based on Massachusetts Locations

One of the reasons I love photographing engagement sessions in Massachusetts is the variety! Beaches, forests, historic little towns, and big city streets all bring a different mood to your session, and how you dress can either enhance or compete with that environment.

Here's how I typically guide couples based on their session location:

Beach Engagement Sessions

Massachusetts beaches tend to have softer, more neutral backdrops — sand, blue skies, water — which gives you a little more freedom with color and texture.

Here are some of my favorites for the beach:

• Light pastels

• Soft blues, blush tones, and creams

• Light-wash denim with white or neutral tops

• Flowy fabrics that catch the ocean breeze

Patterns can also work well here since the space itself is pretty simply visually. You just want to avoid anything that's really bold or neon because it'll clash with the natural environment.

Forest or Nature-Based Sessions

Forests always have a dreamy, whimsical, and intimate feel, but the lighting can be a little tricky with the extra tree cover.

If you want your session somewhere that has more shade, you want to:

• Wear lighter colors (white, cream, soft neutrals) to help brighten the photos

• Avoid heavy browns or greens so you don't blend into the background

Some couples want a moodier, earthy vibe if they choose this type of spot for their photo session, and we can definitely lean into that too! We just have to careful of the balance so you don't disappear into the scenery — the focus should be on you after all.

Historic Towns and City Settings

Locations like Beacon Hill, downtown Boston, or historic Massachusetts towns tend to have a lot happening visually. Architecture, textures, people, and movement all play a role.

In these settings:

• Solid colors photograph best

• Avoid busy patterns that compete with the background

• Feel free to lean slightly more fashion-forward if that feels like you

• Accessories are great for this environment

  
  

City sessions are truly the perfect place to wear a more elevated outfit, but make sure if we're walking around a lot, you still feel comfortable and natural.

Colors and Patterns to Avoid

I'm not the wardrobe police, but there are a few things I generally recommend avoiding for engagement sessions.

Very Bright or Neon Colors

Think magenta, red, orange, bright yellow, or anything neon.

These colors tend to reflect onto your partner’s skin, which can make skin tones look uneven and creates extra challenges during editing.

Tiny Patterns

Small checks, tight stripes, or tiny polka dots can create something called moire, which shows up as a strange wavy effect in photos (especially on jackets or structured fabrics).

Overly Contrasting Textures

Leather next to heavy corduroy, for example, can feel visually disjointed, so it's best to avoid competing with each other!

The Biggest Outfit Mistake Couples Make

This one's important, so if you only listen to one piece of advice, make sure it's this one:

DO NOT MATCH EACH OTHER!

Coordinating is great. But matching is not.

That means:

• Don't wear the same shirt color

• Don't wear the same denim wash

• Don't both wear bold patterns (or the same pattern)

Instead, aim for colors that mesh well together. You want to complement each other in your photos, not look identical.

And if you're unsure, I'm always happy to weigh in! Many of my couples send me outfit options before their session, so don't be shy and send some pictures my way.

One Outfit Or Two?

If possible, I strongly recommend bringing two outfits.

Having two looks gives you two different moods in your gallery. One outfit can feel more elevated and polished. The other can feel relaxed and casual.

I usually suggest starting with the dressier look since hair and makeup are freshest at the beginning of the session. As the session goes on, couples naturally become more comfortable in front of the camera, which makes the casual outfit feel even more natural.

Some Practical Tips For Your Massachusetts Engagement Session

There's more that goes into looking your best in your photos besides just picking out your outfits. These final tips will make a huge difference:

• Steam your clothes. Wrinkles are more visible than you think, so you will notice them in your final photos (and no, I can't edit them all out!)

• Change at the location if you're driving far. Saves you from seat wrinkles!!

• Bring walking shoes if needed. I know your outfit might look better with heels, but if we're walking around a lot (especially in the city), you'll be more comfortable slipping on some flats or sneakers and then swapping them out just for the photos.

• Coats can be cute! In Massachusetts, we're at the mercy of all four seasons, so if your engagement session is scheduled during a cold snap, make sure you bring a coat. They can be a great addition to your outfit, or you can use it to warm up between shots if you don't want to cover up what you're wearing.

• Skip the purse. I don't want you to carry around your purse (or worse, shove everything in your pockets), because it limits movement and doesn't allow for candids. I'll happily hold your keys, so try to come with the bare minimum.

Final Thoughts

Bride and groom hugging in city

Bride and groom smiling in front of large building

Your Massachusetts engagement session is not about dressing perfectly or following a list of rules. It is about showing up as yourselves and allowing your connection to come through naturally.

Wear something that feels like you on a really good day. Choose pieces you can move in, laugh in, and feel comfortable enough to forget about once we start shooting. When you feel good in what you're wearing, it shows in your photos.

And remember: the most meaningful engagement photos are not the ones that follow every trend or Pinterest guideline. They're the ones where you look relaxed, present, and where you can genuinely enjoy each other.

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Want to keep exploring? Here's what you can do next:

Learn more about my photography services. If you're interested in engagement sessions, wedding coverage, or learning what working together actually looks like, head over to my wedding experience page. I'll walk through what I offer, how the process works, and what you can expect from start to finish.

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