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17 Tips for Choosing Your Engagement Session Outfits

Let’s Face It, Professional Engagement Photos Can Feel Intimidating

I don’t know about you, but having your photo taken can be kind of intimidating . . . even when it’s just on a friend’s iPhone! So when it comes to having your engagement photos taken by a professional, there can understandably be some stress over how to look your best for them. Know that this is perfectly normal and something that most couples talk to me about. This is exactly why I wanted to share some of the best tips I have for how to show up looking and feeling your best for your engagement session.

couple in the boston public garden for engagement photos

Embrace Your Style and Dress for Comfort

  1. First and foremost, I want you to wear whatever makes you feel like you! Comfort really is key. If you feel uncomfortable in your clothing, it will show on camera. Listen to your gut when it comes to what you feel good in. Some couples love an excuse to go all out on a fun, dressed up outfit. Others prefer a more casual, but polished look.
  2. It is entirely up to you, but most of my couples choose to wear two outfits at their engagement session. One “us on a cute, casual date” outfit and one more formal outfit. This will give your session two different looks, and I recommend beginning with the “cute date” outfit first (as this will help you to feel more natural as we all warm-up).
  3. If it is your style, don’t be afraid to dress things up! Your engagement session is the perfect opportunity to rock a fun, dressed up look that you might not normally have an excuse for. Long, flowy dresses and skirts look amazing on camera — they add movement to your clothing that tends to be very flattering and natural-looking. That being said, if you’re a very casual couple that hates to dress up, don’t feel pressured to wear anything that you don’t actually like.
How to Dress for Your Engagement Session | Photo: By Halie

Choosing and Coordinating Colors for Your Engagement Session Outfits

  1. Focus on coordinating colors, not matching colors. If you both wore the same exact color tone to your engagement session, how boring would those images be? For example, if you wear a blush dress, soft blue chunky necklace, and nude heels, then your partner might wear a navy coat with khaki or gray pants, paired with brown leather shoes and maybe even a blush pocket square. You each tie in the main color that the other is wearing (blush for you, navy for them), and create a well-coordinated look that isn’t too matchy-matchy.
  2. I generally recommend selecting lighter tones and more muted shades. Very bright, bold colors (think, like hot pink or cherry red types of tones) can sometimes distract viewers’ eyes to go to your clothing and not your faces.
  3. The above being said . . . the above is a rule that can be broken when done well. Sometimes, a pop of color can be the perfect touch for your engagement session color palette! Bethany’s yellow sweater (below) completed her and Patrick’s look. The key was having one big pop of color — and the tone was subtle enough that it complemented the overall look. Like all good things in life, it’s all about balance!
a couple doing their engagement photos in boston's seaport area. he's wearing a jacket and she's in a white dress.

Flatter Your Features When Selected Your Outfits

I’m going to preface this ENTIRE section with some reassurance that you’ll look incredible at your session. That being said, you’re only human and it’s natural to have some features that you’re self-conscious about at times. This section is intended to be preventative if you suspect that you may nitpick parts of your body (let me say it again, you’ll look GORGEOUS at your session). If this is you, the best thing to do is recognize anything you may be self-conscious about and choose clothes that best complement those feelings. When you wear clothes that make you feel comfortable and confident, you’ll look comfortable and confident on camera! Here are a few common concern areas:

  1. Arms: Three-quarter length sleeves can help to create a slimming effect on all arms. You could also bring a cute jacket, blazer or cardigan along. Skinny straps or strapless dresses can have the opposite effect on arms, so I recommend avoiding those if you find yourself focused on your arms a lot.
  2. Legs: Heels tend to elongate the look of women’s legs (especially closed-toe heels!). If you do choose to wear peep-toe heels, remember to give your toenails some love before your session too.
  3. Height differences: This can go both ways! Make sure that you’re comfortable with your shoe height and where that puts you next to each other if this is something you’re self-conscious about. Overcompensating with a subtle dip down or a tiptoe up can turn a cute pose into an awkward look.

No matter the concern, know that you look incredible. When you feel comfortable and confident, it really does show!

A couple in Charlestown, MA doing their engagement photos along the waterfront. He's in a blue button down shirt and she's in a white dress.

Add Details to Complete Your Session Outfits

  1. Be bold with layers and accessories — jackets, sweaters, necklaces, scarves, belts, etc. all add dimension to your photos. Layers like jackets, sweaters, and scarves also make it easy to give yourself two “looks” without actually changing your outfit.
  2. MOST patterns are okay for photos . . . but, graphics are not ideal. If you’re wearing a pattern, make sure it’s not overwhelming and distracting. Similar to choosing colors, we want to first draw attention to your faces, not your clothes.
  3. Empty those pockets, literally. Guys, this one is generally most applicable to you. You’ll regret seeing your cell phone or keys showing through your pockets.
What to wear to your beach engagement session in MA

Go Pro with Hair and Makeup

Professional hair and makeup can be a great option because it looks amazing and removes the stress of getting ready on your own. It’s also a good way to get an extra boost of confidence!

If your wedding is local, your engagement session could also be the perfect time to do your makeup trial. It can be easy to feel like your makeup is too much at first since it’s more than you would wear on a normal day — know that this is a normal feeling, but that a good makeup artist knows how to get it just right for the camera! Doing this for your engagement session, you’ll get to see how the makeup photographs. There is NO going back on your wedding day, and this is the perfect way to know for sure that you love it.

Don’t forget that your ring will get some attention on this shoot, so give yourself permission to get it cleaned and your nails done, too!

Chic couple in the Boston Public Garden looking stylish for their engagement photos

Engagement Session Outfit Tips for Men

  1. Long pants and closed-toed shoes will give you a sophisticated and masculine look for your photos. Whereas shorts and open-toed shoes can draw attention to your legs and feet, the former creates a sleek look for your engagement session. Suit pants, dress pants or colored pants work best. Brown leather dress shoes complement almost every look, whether you’re wearing a full suit, blazer, or simply a collared shirt.
  2. Talk with each other to make sure that you’re both dressed on the same level of formality. It can be common for one partner to like dressing up more than the other, so finding the common ground in between for you both can be big for your engagement photos.
  3. Like we discussed already, layers can add a ton of interest and dimension to your photos! Blazers, vests, and coats are all easy enough for you to have multiple looks without changing your outfit. Likewise, ties, bowties, pocket squares, colored socks, belts, tie clips, suspenders, and watches can all be fun accessories for you to consider as well. Use these kinds of accesories to pull in each other’s coordinating colors.
How to Dress for Your Engagement Session | Gibbet Hill Engagement Session

Your Engagement Session Packing List

Here are the things I remind my couples to bring along to their engagement session:

  • Flats or flip-flops for walking between photo locations (if you’re planning to wear heels)
  • Outfit two (including shoes and accessories), if you’d like a second outfit
  • Touch-up makeup
  • Water bottle (for warmer sessions)
  • Coat or cover-up (for colder sessions)

I know I just gave you a lot to think about. I wrote this blog post to help guide you through some of the decisions you have on what to wear to your engagement session, and hopefully, it’s done just that. If you’ve taken away nothing else, the most important thing is to wear something that you’re comfortable and confident in! That alone will make ALL the difference in the world.

The final tip that I’ll share today for planning your engagement session — make a date out of it! Make a reservation at a fun restaurant you’ve been dying to try, or make plans at your favorite brunch spot if we’re meeting at sunrise. Even though there are a lot of decisions to make, have fun and enjoy this part of being engaged!

For more wedding planning tips, explore the Advice section of the blog!

comments +

  1. […] 17 Rules for Choosing Your Engagement Session Outfits […]

  2. […] 17 Tips for Choosing Your Engagement Session Outfits […]

  3. […] outfits and shoes you feel comfortable in! You don’t want to look or feel uncomfortable during your […]

  4. […] outfits and shoes you feel comfortable in! You don’t want to look or feel uncomfortable during your […]

  5. […] the Napatree Point Conservation Area. Ashton and Tommy chose a casual but chic look for their first engagement session outfit — Ashton’s feathered sleeves gave the perfect bit of fun flair to the […]

  6. Fantastic blog! I always go for a custom fit tailored suit for special occassions, since I have gained weight its becomes difficult now.

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