Engagement Session Planning Tips

Orillia sunset engagement photographer

Tips for planning your engagement photo session

My engagement sessions can be as simple or as elaborate as you like. But whichever path you choose – my e-sessions are always laid back and casual.  The focus is to have a little fun, gain some comfort with the camera and let loose for some great photos. I’ll give you plenty of direction to guide you however I don’t micromanage the little things… those little things are the subtleties that make make each of us different. And different is great!

For me, it’s amazing how much you can learn about people just through hanging out with them for an evening. It helps me learn how you guys “do you”.  Once your wedding day arrives, you’ll feel comfortable in front of the camera allowing you to focus on your day!

Strawberry picking engagement photo

Strawberries in a basket


While I’m able to shoot anywhere, I have a few location suggestions below to spark your engagement session planning.  The only real thing to note is that I don’t shoot in the city, for me concrete cities are a nothing-burger when it comes to photos. The water, rocks and trees of Muskoka are where it’s at!

  • Orillia:  There are a series of hiking trails, woods, fields and waterfront all around Orillia and close to Hwy 11.  Places like Scout Valley and several conservation areas are some of my favourites.  These areas have dense woods as well as open areas of grass  and different types of trees. They’re favourite hiking areas for my family.
  • Collingwood:  From the top of Blue Mountain and down in the village to the Collingwood waterfront, this area has some of my favourite “go-to” spots for engagement sessions. While I have to charge for my travel to Collingwood for engagements, it’s an amazing area to shoot and I have an ever-growing list of awesome places to shoot there.
  • Stephen Leacock Museum:  This classic Victorian style building was once the home of Canadian royalty, Stephen Leacock. Now a museum, the grounds are large and it’s right on the water in Orillia.  There’s an old classic boathouse as well as gardens and walking trails (it’s a very large property).

Muskoka engagement photography

Laughing pre-wedding engagement photo


  • Shoots take place during weekdays Monday through Thursday in the warmer months and in the colder winter months I have more options for weekend shoot dates if needed. The benefits to shooting during the week are trails and shoot locations tend to be less busy and we’re able to schedule further in advance.  The more lead-time we have the more time you’ll have for Save the Date cards and any prints you’d like to have to showcase at the wedding.
  • Each session is about 2 hours in length and begin 2 hours before the sun sets which gives us the best options for lighting.
  • If you’re planning on having hair and makeup done be sure to give yourself a significant amount of buffer time in case the hair/makeup appointment runs longer than expected (they do quite often).
  • Anticipate traffic.  While we don’t get an overload of traffic up here in Muskoka, oftentimes traffic does build on Hwy 400 during your travel here (ie. Barrie!)

Pre-wedding Muskoka engagement photo

Engagement photos at sunset


First let me start by saying that I’m by no means a stylist (my wife can back me up on this), however these are a few simple tips to help you look our best on camera.

  • Simplicity.  Solid colours I feel work best as opposed to patterns and stripes as they often conflict with other elements of the photo. Neutral colours like beige, white, black and grey often photograph the best.  Bold colours tend to take away from the focus, which is your face and  connection.  Now with that said, if bold/bright colours suit your personalities then I say bold-it-up no question!
  • Logos. Avoid logos whenever possible as they’re often distracting
  • Changing outfits.  It’s not necessary of course however if you’d like to go for a couple different looks during our session please feel free.  I don’t recommend more than two outfits just so we’re able to maximize the time we have together.
  • If you normally wear glasses don’t worry about glare, I’ll shoot accordingly.
  • Avoid baggy clothes.
  • Footwear. Keep our shoot location in mind when selecting your footwear.

Guitar engagement photo

Muskoka engagement photographer

Engagement photography in Midland, Ontario


  • Connection.  I often find that the best photos are the ones where you and your partner are in your own world enjoying one another and not looking into the camera. You’ll likely hear me say it a few times, connection is key.
  • Props.  It’s not necessary to accessorize your session with props however they’re certainly welcome if you have some you would like to bring along.
  • Hands Free.  I recommend having your hands free throughout the session so for example not carrying extra clothing, purse, drinks etc. If there are some things you need to bring like props, phones, drinks then bring a bag where everything can stay. This keeps us mobile as we’ll have less to lug around  and worry about.
  • Pets.  This kind of goes with the hands free recommendation previously.  I love pets and they’re certainly welcome however they can sometimes slow things down a little because, well their priority isn’t necessarily waiting around for your photos. In these cases I recommend bringing a friend/family member to watch your pet when they aren’t “needed on set”.
  • Hair.  Now isn’t the time to try a new haircut or makeup style that you’re not 100% on board with.  Avoid those new-hairdo tan lines.
  • Tanning.  I don’t recommend tanning in the days leading up to your session. A tan may look good in person however cameras are sensitive to skin tones and natural colour is most flattering in photos.

Creative engagement photographer in Orillia Ontario

Astilbe Boutique decor


Looking for a complete photo shoot experience? One of the perks of being a wedding photographer is working with so many amazing wedding vendor teams each weekend – teams I can call on when the time is right!  If you want the full monty engagement shoot experience I offer hair + makeup as well as a decor florist option to take your engagement shoot to the next level.  If you’re interested in upgrading your session with my team of professionals just say the word!

Connect with me… 
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jordan ashley hair makeup



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1866 Elana Drive, Orillia, Ontario Canada

(705) 627-9376