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Engagement, For Brides & Grooms

April 20, 2015

How to Plan Your Perfect Engagement Session

This blog post is long overdue! I’m so excited to finally put together a “how-to” guide for my KDP couples on how to prep for your engagement shoot. For most of you, this will be your first time getting professional photos taken together. It’s a fun time where we can get to know each other before your wedding! I love getting to know my couples so that I feel more like a friend on your wedding day and not just another vendor. Your engagement session is the perfect time to get any nervous jitters out about being in front of the camera, and then by the time your wedding rolls around you two are old pros in front of my camera :)

Here are some tips to help you plan your perfect engagement session!



The location sets the whole tone for your engagement session! Engagement sessions are the perfect time to show off YOU and your story as a couple. I strongly believe that a location with sentimental value really adds a lot of meaning to your photos! Here are some examples below…

If you live in a different city than you’ll be getting married, your engagement session is the perfect time to show off you two in your hometown!


Let’s take your engagement photos of you two doing something you love! Whether this is skiing, visiting your local coffee shop, taking a cruise on your sailboat… Basing your location off of something you two love to do together can make for fun & unique engagement photos!

Ski Inspired Engagement Session

Having your engagement session where you met can be another great location idea! Just simply being back in the place where your relationship started can evoke so much happiness & love that come through in the photos :)

University of New Hampshire Engagement Session


This is always a tough question! Trust me, every time I’m going to have my pictures taken I’m in the same position of “What to wear?!” which usually ends in a shopping spree. Here are a few things to go by…

Whatever you wear should be YOU. Don’t go out & buy something new just for the sake of engagement photos that you wouldn’t likely wear ever again. Engagement photos are your chance to show off your personal style!

How To Prepare for Your Engagement Session

Bring 2 outfits: One a little more casual & one a bit dressier. How dressy & how casual you get will depend on how you guys dress on a day-to-day basis. Someone’s “casual” might be another person’s “dressy” and that’s okay! Having two different outfits will give you a variety in your photos… more to love!


If your style & location calls for you to go dressy, consider Rent the Renway! It’s an awesome website where you can rent dresses & accessories just for a few days… Genius. All of the glory at a fraction of the cost. They have everything from cocktail dresses to floor length gowns and everything in between!


Dress for the location & season! If your engagement session is in the winter, make sure to bring jackets that you won’t mind wearing for some of the photos. If you’re going to be on the beach or by the water, think flip flops or nautical stripes! Also, don’t forget about the footwear! If we’re going to be shooting in a city that likely means we’ll be walking quite a bit. If you’re not comfortable in heels, consider wearing flats or bringing shoes you can walk in.

Boston Engagement Session

Maine Engagement Photos

How To Prepare for Your Engagement Session

As your browsing your closets, I would recommend laying out the outfits you two are considering wearing side-by-side. Since you two will be snuggled up right next to each other for most of the engagement session, laying your outfits out by each other will allow you to see if any of your colors or patterns clash with each other.

Nantucket Engagement Photos


Beyond your location & what you wear, there are lots of ways to add personal touches to your engagement session! I’m not generally not a huge fan of signs & props, but fun little touches can really add a lot to your session!

You can bring your favorite books, if you’re coffee drinkers you can bring mugs, we can plan on a picnic with your favorite blanket…. Anything that represents you two as a couple!


Incorporating your pet! Allowing your furry friend to come along for part of the session can add such cuteness to the photos. Katelyn James just wrote an awesome blog post about incorporating your dog into your engagement session… Check it out HERE!

How to Plan Your Engagement SessionNantucket_Wedding_Photographer


The day or two before your session, here are a few things you can do to really give your photos a polished look!

This might be obvious, but make sure your clothes are in tip-top shape! Whether that be dry-cleaned, ironed or lint-rolled, it’s just nice for your outfits to look their best.

How to Prep for Your Engagement Session

Treat yourself to a manicure & a ring shine! Your hands are going to be in these photos A LOT because of that beautiful shiny ring you’re now sporting on your left hand :) There’s no better excuse to treat yourself to a manicure! If you don’t want to go that far, at least just make sure your current polish isn’t chipped. It’s also a great idea to get your ring cleaned to really make it SPARKLE! In my opinion, taking it to a local jeweler is the best way (a lot of jewelers offer it as a complimentary service) but there are also lots of online tutorials on how to do this at home.



Consider getting your hair & makeup professionally done for your engagement session. This can make a HUGE difference in your photos! For me, I can put together an everyday look, but my cosmetic knowledge & skills don’t extend much further than my Cover Girl mascara and my Chi straightener. Let the professionals go to work for you & take the stress off of trying to do it yourself! Last year I interviewed my dear friend Candace of Colour By Candace and here’s what she had to say about makeup (you can read the whole blog post HERE):

“As far as makeup goes, I get a lot of requests for “natural” makeup. Natural makeup does that mean no makeup. The camera will take off half of it, so you have to put on a decent amount of makeup to make you look your best in front of the camera. You really need to trust your HMU artist and trust that they know what they’re doing.”

How to Prep for Your Engagement SessionVermont_Elopement_Photographer


Whew! I know that was a lot of information to take in! You can always take a look at good old Pinterest… I have a board specifically devoted to helping couples plan their engagement sessions.

Follow Kelsey DeWitt Photography’s board KDP: Engagement Session Inspiration on Pinterest.

Above all, remember that no matter where your engagement session is or what you’re wearing, we’re going to have a blast getting to know each other!

  1. Deborah Z. Parker says:

    Beautiful images and great tips Kelsey!:)

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