Engagement Photo Shoot Planning

Orillia sunset engagement photographer

Tips for planning your engagement pictures

Engagement photo shoots 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 some fun, get comfortable with the camera and get to know each other a little. 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 couple unique. And that’s the good stuff!

It’s amazing how much you can learn about people just hanging out for an evening.  I learn how you guys “do you” – are you goofy, romantic, daring etc.  Your personalities will guide our shoot.

Strawberry picking engagement photo

Strawberries in a basket


I have a few location suggestions below to spark your engagement picture planning.  The only real location I avoid is the city, for me concrete cities are a nothing-burger when it comes to photos. The water, rocks and trees of Muskoka are where I like to play.

  • Orillia:  There are a series of hiking trails, woods, fields and waterfront all around Orillia that are 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 also favourite hiking areas for my family.
  • Collingwood:  The top of Blue Mountain, Blue Mountain Village and the Collingwood waterfront are amazing locations for engagement photos. While I have to charge for my travel to Collingwood for engagements, it’s a great area to shoot.
  • 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 with a boathouse as well as gardens and walking trails.
Stephen Leacock Museum Wedding photo

The Leacock Museum is great for engagement or wedding photos

Muskoka engagement photography

Laughing pre-wedding engagement photo


  • My summer and fall engagement photos typically take place Monday through Thursday and winter engagement photos have more flexibility for weekend dates if needed. The benefits to shooting during the week are that trails and shoot locations tend to be less busy.
  • Each session is approx. 2 hours in length and we start shooting a couple hours before the sun sets which gives us the best lighting.
  • If you’re planning on having hair and makeup done be sure to give yourself sufficient time in case the hair/makeup appointment runs longer than expected.
  • Anticipate and factor in potential traffic – the sun waits for nobody so we need to start on time.

Pre-wedding Muskoka engagement photo

Engagement photos at sunset


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

  • Simplicity.  Solid colours I feel work best as opposed to patterns and stripes.  Patterns like these can often conflict with other elements of the photo. Neutral colours like beige, white, black and grey often photograph the best.  Bright/bold colours tend to take away from the focus, which is your face and  connection.  Now with that said, if  ‘bold and bright’ suits 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 however if you’d like to go for a couple different looks for your engagement pictures then I say go for it.  I don’t recommend more than two outfits 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 and season 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 your time together and not gazing into the camera.  Connection is key.
  • Props.  It’s not necessary to bring engagement photo props however they’re certainly welcome if you have some you would like to bring along.  If so, I recommend things that are personal to you more than something you saw in Pinterest that while cool, doesn’t necessarily represent you and your partner.
  • Hands Free.  I recommend having your hands free throughout the session. 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.
  • 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. I recommend bringing a friend/family member to entertain your pet when they’re not 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.  And for the fellas, a new-hairdo means new-hairdo tan lines.
  • Tanning.  Don’t overdo it.

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 vendors – vendors I can call on when needed.  If you want the full monty engagement shoot experience I have a team that includes hair + makeup, decor florist and videography 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