Engagement Photo Session 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.

    Best time: Year Round
    This is a series of trails through the woods with a few fields and small stream. It’s a popular spot for my family when we feel the need for a fresh air hike. It offers a variety of photo opportunities for those who love the outdoors.
    Best time: Fall, Winter
    Each Fall after Thanksgiving, Bass Lake Provincial Park opens their back gate to the public and it’s a great spot with tall mature trees, trails and beach with an amazing view of the sunset. Great option for fall and winter shoots.
    Best time: Summer, Fall
    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.
    Best time: Summer, Fall
    A beautiful venue just outside of town with amazing gardens, fields, pond and tall mature trees. Best in summer and fall however scheduling is tight as it’s a popular wedding venue. Please note that since this is a venue they often have events planned or may not be available for a host of reasons.

Stephen Leacock Museum Wedding photo

The Leacock Museum is great for engagement or wedding photos

Muskoka engagement photography

Scout Valley is great year round for trees, trails and fields.

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. 90 minutes 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

Winter engagement photography Orillia

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.  As for colours, I’ve leave that to you. If you like your neutral, earthy tones then roll with it.  If  ‘bold and bright’ suits your personalities then I say bold-it-up!  Do you.
  • 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


  • 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