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Engagement Session FAQs: What to Wear?


Well, I am officially in the middle of Engagement Session season!  Spring and early summer are always full of engagement sessions, and rescheduling engagement sessions due to rain, while I tend to have more weddings in late summer and the Fall.  I get a ton of questions every year around this time, so I figured I should continue with my Engagement Session FAQ series!


Up next:  What do I wear for my Engagement Session?!


Wear something you can breathe in, walk around, sit down, or jump around in.  No matter what we end up doing for your engagement session, I can promise you we’ll be walking around.  I wouldn’t put it past me to sit or lay you on the ground or on some random steps.  If you want to do something active, dressing comfortably is doubly important.  So, comfortable clothes and comfortable (or at least bearable) shoes are key!  Nothing too tight, or itchy, or anything that will make you any more uncomfortable than having a camera in your face already does ;)

Nora & Troy



Hingham Engagement Session


Wear something you love – something you know makes you look good!  Every girl has that outfit that they totally love, they wear it all the time because it just makes them look and feel fabulous.  That’s the one you want to wear!  The outfit that makes you feel totally confident.  No buttons are going to be popping open, you’re not going to tell me after the pictures come out that those jeans make you look fat, none of that!  Look at yourself in the mirror and look for things that might drive you nuts in a photo later… if it drives you nuts, pick something else!  If you’re super fair, avoid white.  If you’ve got red hair, maybe skip red.  If you need some tips watch a few episodes of What Not To Wear – or better yet, ask your fiance what he thinks makes you looks awesome!  I’ve had too many brides pick out an outfit in a hurry and tell me later that they hate what they were wearing, which makes the photos way less fun, believe me.  So, choose something that makes you feel GOOD!!

Boston Engagement Session

Boston Engagement Session

Portsmouth Engagement Session


No matter where we go, or what we end up doing, you should dress for the occasion!  If you’re going downtown for some fun, urban shots – maybe dress up a bit.  If you’re going for a hike in the woods… maybe skip the silk dress and the heels, and opt for jeans.  If it’s November and snowing, you should plan on wearing your coat, so pick one you like.  If it’s going to be 100 degrees and sunny, keep that in mind.  If we’re going to be doing something messy, don’t wear anything toooo nice…  You get the idea.

Fishing Engagement Session

NYC Engagement Session


Cape Cod Engagement Session


You want to make sure you look good, but you also want to be sure you look good together, right?  You should try to neither clash, nor be too matchy matchy.  Patterns and colors are GREAT!  Just make sure they look good side by side.  And, you should aim to be at about the same level of dressyness or casualness.  If he’s in jeans and a wifebeater and you’re in a hot dress and heels… you may have bigger issues than your photos ;) – either way, the photos will definitely look weird.  Now, if you two are polar opposites on a lot of levels, including fashion, it could be fun to do some photos that mark the contrast.  But most of them should be somewhere in the middle, finding your common ground and focusing on that.

Alli & Glenn's Engagement Session

Hingham Engagement Session

Walden Pond Engagement Session

New York City Engagement Session


Gentlemen, let me encourage you with a few tips just for the guys…

  • I know most of you aren’t really into the whole engagement session thing in the first place.  I promise, it’s going to be fun though!!!  Even if you’re not super excited, put a little effort into it anyway.  It’ll make your bride happy, and it will pay off in the end when you’ve got some awesome photos of the two of you.  A little effort goes a long way and when I’ve tagged all these pics of you on facebook, you’ll be glad you made the effort to look your best :)
  • Ask your fiance what she thinks looks great on you – and wear it!
  • Wear clothes that fit!  I’m begging you guys…  enough with the saggy pants!  Wear your least saggy pants, and a shirt is neither skin tight nor 4 sizes too big.  I mean, if your girl is wearing the saggy pants too, then go for it.  But if she’s dressing it up a bit, non-saggy pants will really kick your outfit up a notch ;)
  • Your shoes matter.  There’s a pretty good chance I’m going to get your shoes in the photos… there may even be photos OF your shoes.  So, keep the shoes in mind and don’t try pairing up Air Jordans with slacks, ok?
  • Get a haircut.  And maybe even shave?  You want to look like YOU, so don’t do anything crazy like grow a mustache that week ;)
  • Follow Tips 1-4 as well
  • HAVE FUN!!!!

You know I love you guys!  Just trying to help you out :)

Rockport Engagement Session

Boston Engagement Session

Harvard Engagement Session

Tip #6:  LADIES

Ladies, here are a few tips just for you too…

  • Hair…  wear it however you like it best!  You want to look like YOU, so I don’t recommend going too fancy.  Your engagement session day is not the best day for a test run for your wedding hair.  We’ll get pictures of that hair-do, plenty!  We want the engagement photos to look a little more natural than that.  Consider getting a blow-out at your salon if you want it to look extra nice.  Just keep in mind what we’ll be doing together, and what the weather’s going to be like.  I’ve got super curly hair, and if you’re like me, you do not want to try straightening your hair before a shoot on a super humid day!
  • Make-up… again, go fairly natural.  That is, natural for you.  If you like a lot of make-up, then go for it!  Go all out!  If you’re the girl who never wears make-up… maybe consider having it done or at least putting a little on yourself.  A little cover-up, lipstick & mascara can go a really long way to make your features pop in photos!
  • You might want to do your nails – at least file them and make sure there’s no chipped paint on them (toes and fingers).  Cleaning your ring might be a good touch as well.  I focus a lot on hands…
  • Don’t bring your purse with you!  You won’t need your purse, or your cell phone, or anything like that while we’re shooting – and if you do, we can always go back to the car for them.  I shoot a lot while we’re walking, so if you’ve got a ton of stuff, it’s going to be in the pictures (or I’m going to end up carrying it along with all my gear ;)

New York City Engagement Session


Boston Engagement Session

Tip #7:  WHAT TO BRING (and leave in the car)

  • A change of clothes, if you want to go for another look later in the shoot
  • A blanket if you don’t want to get your butt dirty if we need to sit in the grass or something
  • Bug spray & sunscreen or a scarf & gloves, depending on the time of year
  • A ponytail holder… you never know when you’ll want to pull your hair back.  Right, guys?  ;)
  • Props… if you want.  A lot of folks are doing themed engagement sessions these days.  I’m totally up for that, if you are.  We can think up some stuff ahead of time.
  • Your sense of humor!  Engagement Sessions are totally strange for most people, so be prepared to laugh and enjoy a little awkward quality time with your fiance ;)

Ok, those are my tips!  I hope this helps!!!  No matter what you wear, we’re going to get some great photos of you!  These are just my suggestions for getting the best photos we can :)


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