Top Engagement Photo Tips: How to Look Natural and Feel Confident in Your Engagement Session
Hey future photo pros! So, you're gearing up for that oh-so-exciting engagement photoshoot. But before you jump in front of the camera, let's chat about how to make this whole experience a breeze.
Think of preparing for your engagement photoshoot like prepping for the ultimate adventure—minus the bug spray and hiking boots (unless that's your vibe, of course). From scouting out the coolest locations to picking outfits that scream "couple goals," we're here to dish out some seriously handy tips and tricks.
So grab your partner-in-crime and get ready to strike a pose, because we're about to turn your engagement photoshoot into an epic memory-making extravaganza. Let's dive in and make some magic happen! 📸✨
How to Choose a Location for Your Engagement Session (Hint: It Should Mean Something)
Picking the perfect spot for your engagement session doesn’t have to be stressful. The best locations are often the ones that already matter to you — places tied to your story, your routines, or just somewhere you feel completely at ease.
DO:
Choose a location that’s meaningful or nostalgic — where you had your first date, got engaged, or even where you just love spending lazy Sunday mornings together.
Think of local spots that already feel like you — coffee shops, bookstores, markets, or your go-to walking path.
Keep it simple. A cozy at-home session can be just as powerful as any skyline backdrop.
Make sure there’s parking or a private space if you want to change outfits mid-session.
DON’T:
Forget that some locations require permits — we’ll help you check this ahead of time.
Let all the choices overwhelm you. Not sure where to start? Think of a vibe: urban, moody, cozy, woodsy, dramatic, minimal, action-packed — and we’ll help you build something from that.
Worry about being “too out there.” If it’s meaningful or exciting to you, let’s make it happen.
Real Talk: Vince & the “Just a Coffee” Moment
One of my favourite examples of this was Hubert & Vince’s Port Credit engagement session.
We’d wrapped up a golden hour shoot by the water, and Vince casually mentioned wanting to stop by a Starbucks nearby. But not just any Starbucks — it was the one where he used to be a manager. It held real meaning for him, and he thought it’d be cool to just “grab a coffee.”
How to Choose a Date for Your Engagement Session (Timing Makes the Magic)
When should you do your engagement session? There’s no one-size-fits-all answer — but the date you choose canshape the whole vibe of your shoot. Think about light, weather, location, how you want to use the photos, and most of all, how you want the session to feel.
DO:
Leave yourself enough time before the wedding to use your photos in save-the-date cards, your wedding website, or as prints for your reception decor.
Consider how each season changes the mood: winter brings soft light and snow, spring gives blooms and colour, summer adds warmth and movement, and fall is all about golden tones.
Know that weather is unpredictable. Blooms can come late, leaves can fall early, and flexibility is key.
Be prepared for crowded parks in spring — especially during cherry blossom or tulip season.
DON’T:
Wait until late fall (November) for outdoor shoots — it’s the in-between season where everything looks a little… meh. No leaves. No snow. Just grey.
Dismiss winter sessions. Snow adds beautiful contrast, softness, and a lot of fun.
Real Talk: Christine & Cesar Wanted Water — So Summer Was Non-Negotiable
Christine & Cesar’s Woodbine Beach sunrise engagement session was 100% driven by their vision: they wanted to play in the water, splash around, and capture that carefree, romantic summer vibe.
Their inspiration? Kyla & Riley’s Kelso Conservation Area session, where we ended the shoot mid-lake with soaked clothes and giant smiles.
Christine knew she needed that same kind of moment — and to get it, we had to commit to a warm-weather date. And wow, did it pay off. They owned the sunrise, the shoreline, and every frame we took.
How to Choose a Date for Your Engagement Session (Spoiler: Timing Is Everything)
When it comes to engagement photos, timing can change everything — from the vibe of your photos to how and where you end up using them.
DO:
Plan ahead. Leave enough time before your wedding if you want to use your engagement photos for save-the-dates, your wedding website, or as printed decor at the reception.
Think about seasonal vibes: spring blossoms, golden fall leaves, cozy winter snow, or sun-drenched summer. Each one tells a different story.
Keep in mind that weather can be unpredictable. Spring doesn’t always mean blooms, and fall doesn’t always deliver peak colour. Flexibility is key.
Expect crowds in public parks during peak bloom seasons (especially spring). We’ll work around it or pick quieter spots if needed.
DON’T:
Wait too long into late fall — November can be tricky with bare trees and no snow yet.
Count out winter sessions! Snow creates soft, magical light, and winter engagement sessions can be cozy, intimate, and way less crowded.
A Winter Session Dream Come True
Take Christine & Stephen’s winter shoot at Trail Hub for example. Christine really wanted snow in her engagement photos — but it was one of those unusually warm winters in Toronto, and the city just wasn’t delivering.
So, we headed a little further north to Trail Hub. Not only did we find the perfect patch of snow to bring Christine’s vision to life, but the indoor spots at the venue were an absolute dream to shoot in. Rustic, warm, full of character — honestly, Trail Hub is a gem for winter engagement sessions and wedding days alike.
Moral of the story? With a little creativity and flexibility, you can still get the exact look you want — even if the weather’s not playing nice.
What to Wear for Your Engagement Session (With a Real Example That Nailed It)
Feeling unsure about what to wear for your engagement photos? You’re not alone. Outfits can seriously affect how confident and comfortable you feel during your session — which is exactly why we include this list of DOs and DON’Ts for every couple.
DO:
Match your outfit to the location, season, and mood of your shoot. If you’re headed to a cozy park or urban street, leave the tux or floor-length gown at home and opt for something that fits the scene.
Treat yourself to a new outfit — because hey, you don’t get pro photos taken every day.
Pick clothes that make you feel comfortable and confident.
Consider the weather — dress light if it’s hot, layer up if it’s chilly.
Choose light or neutral tones like blush, peach, beige, white, or soft blue — they photograph beautifully.
Go bold with bright, rich colours in spring and summer, but balance it out (not head-to-toe highlighter pink).
DON’T:
Go overboard with accessories — you should be the focus, not your earrings.
Get too matchy-matchy. Instead of identical outfits, go for complementary tones or textures.
Wear clothes that are too tight or make you feel self-conscious.
Rely only on formal shoes — we’re usually walking a lot, so comfy shoes are key.
Avoid black and gray clothes. They may be flattering in real life but get lost in photos.
Be afraid to bring a couple options — but think ahead about where you’ll change (and we’re happy to help pick if you’re torn!).
Case in Point: Terri’s Distillery District Session
One of the best examples of this in action was Terri, from Jeremy & Terri’s Distillery District engagement session. She came fully prepped after reading this exact blog — not just with outfit options, but with intention.
She chose pieces that worked perfectly with the urban, textured vibe of the Distillery District, kept her palette bold but not distracting, and made sure everything fit comfortably so she could move naturally. The result? Pure fire 🔥.
Seriously, check out the blog — you’ll see how the right outfit makes the whole shoot feel more like you, and less like you’re playing dress-up for the camera.
Thinking Smart (and Stylish)
Let’s be honest — engagement shoots are an amazing excuse to wear something that makes you feel incredible… but that doesn’t mean you have to drop hundreds of dollars on a new outfit you’ll only wear once.
Case in point: Hema. For her winter engagement session on Toronto Island, she rented a stunning dress just for the shoot. The look? Pure elegance. The cost? Way less than buying. The result? Magazine-worthy photos without the closet regret.
Renting a look (or borrowing from a friend!) can be a smart, sustainable way to level up your engagement style. Whether it’s a formal gown, a sleek suit, or something bold and unique you wouldn’t normally wear — you get to show up and feel 🔥, without the pressure of “will I ever wear this again?”
And no, it’s not “cheating.” It’s called being resourceful — and I fully support it.
💡 Style Tip: Elevate Your Look (Without Breaking the Bank)
Want something a little more laid-back but still elevated? Shannon’s sunset session in Collingwood is the perfect example of cozy layers and soft colour tones meeting golden hour magic.
How to Prepare for the Engagement Session in the Week Leading Up to It
Let’s be real — most couples are a mix of excited and nervous before their engagement session (and that’s totally normal!). Prepping ahead of time will help you feel relaxed, confident, and focused on just enjoying the experience.
Here are a few things to check off your list in the week leading up to your session:
DO:
Try to book your hair and makeup trial for the same day. You’ll look amazing in your photos and get to see how your look photographs before the big day.
Pro tip: these trials can run long — so give yourself time to chill and not rush to your shoot.
Get your nails done — we’ll be doing some close-up shots of your hands and that beautiful ring.
Clean your engagement ring! It takes 5 minutes, it’s often free, and you’ll thank yourself later when it catches the light just right.
Try on your outfits a few days in advance to make sure they fit, feel good, and don’t need last-minute alterations or steaming.
Pack your bag, prep any props, and lay everything out the night before so nothing gets left behind.
Eat something before your session — trust me, hangry photos are not the vibe.
DON’T:
Avoid salty or heavy foods right before — bloating is real, and you want to feel comfortable in your clothes.
Don’t try a brand-new haircut or colour the night before. If it doesn’t turn out how you imagined, you’ll be stuck with it in every photo.
Real Talk: Jordana Nailed It
When I photographed Jordana & Craig’s fall engagement session at Kelso Conservation Area, Jordana timed her makeup trial for that same morning — and it worked out so well.
Not only did she look incredible, but it gave her the confidence to fully lean into the session. Plus, she got to see how her glam would photograph in natural light and soft fall tones — which ended up influencing her final wedding-day look. Win-win.
What to Bring to the Engagement Session (A Little Prep Goes a Long Way)
We’re going to move around, have fun, and capture some real magic — but that magic runs smoother when you’ve got a few essentials on hand. Here’s what we recommend:
DO:
Bring a sturdy bag or backpack to keep your things in one place — trust me, it’s easier to carry and keep track of as we move.
Pack water and snacks (quick + clean options) to keep energy up between shots.
Bring gum — you’ll probably be smooching a lot. 😉
Have a small touch-up kit with makeup basics, a hairbrush, tissues, wet wipes, and blotting paper.
Bring an umbrella if there’s even the slightest chance of rain.
Toss in a few pain meds (just in case — especially if you’re prone to headaches or stress).
Dress for the weather — bring layers, mittens, scarves, even in summer if we’re shooting near sunset.
Want to make it extra personal? Bring props or meaningful items — think picnic setups, instruments, books, champagne, or anything that tells your story.
But…
DON’T overpack. We walk a lot during these sessions, and having too many bags can become a hassle. Keep it light, mobile, and safe — anything we leave unattended is at your own risk.
Real Talk: Emily & John Brought the Vibe
One of my favourite examples of bringing something just right? Emily & John’s engagement session in Prince Edward County.
They brought along a bottle of champagne and two glasses, which we used for a spontaneous little celebration down by a quiet, secret beach. It wasn’t posed or forced — it was them. A tiny detail that turned into one of the most romantic (and photogenic) moments of the session.
So yeah — the right item, at the right time? It can add a lot.
What to do During the Engagement Session
Do trust us and follow our direction!
Do try to relax and have fun with your partner.
Do remember that nervous giggles are totally ok. We never expect our couples to be 100% comfortable in front of the camera, plus they make for adorable photos!
Do focus on your partner.
Do make each other giggle. Tell each other inside jokes, tickle each other, and be silly. Whatever it takes! We don’t judge and just want to see your smiles!
Do stay close to each other and flirt. Hold hands, hug, and snuggle.
Do give each other soft kisses. Kisses on the forehead, cheek, and lips are all welcome. This is the best time for some PDA!
Do be open-minded. While we may ask you to do something silly, often times it’s for your giggles and smiles before and after the action.
Do keep moving and interacting with each other. You can dance, run, or even jump around. Whatever you like! The best moments are the least posed.
Don’t worry if you are nervous. Shake it off, ask for a break, or change what you are doing. The most important thing is for you to be comfortable and have fun!
🔁 Quick Recap: What to Keep in Mind for Your Engagement Session
Planning your engagement shoot doesn’t have to feel overwhelming. With the right prep, you’ll not only feel confident — you’ll actually have fun doing it. Here’s a quick breakdown of what we covered:
✅ Pick a location that means something to you
✅ Choose a date that works with your vision (and the weather)
✅ Think about your outfits — style and comfort are key
✅ Don’t overthink it — renting an outfit or borrowing can be a smart move
✅ Prep in advance (hair, makeup, nails, snacks, outfits)
✅ Bring a bag with your essentials, props, and extras that’ll keep you comfy
✅ Most important: bring the good vibes and I’ll take care of the rest
📝 Want the Checklist? I Got You
I’ve put together a simple, no-fluff Engagement Session Prep Checklist you can download, screenshot, or print. Use it to stay on top of everything — from wardrobe to weather prep.
👉 Download the Engagement Prep Checklist here (← you can link this to a Google Drive PDF, Dropbox file, or embed it right on Squarespace with a download button!)
Need more ideas? Check out these engagement shoots for inspiration!
You Might Also Like…
Sometimes we meet special couples, some couples that just challenge us, some couples that want more than just the regular. Usually most of our couples are like that, but Jess and Jay just pushed that boundaries way way up, and I love that!!!
In the first meeting at their house, I knew from the beginning of our conversation that couple was a little different.
Shooting at an abandoned location of some sorts has been on the bucket list for Diego and I for quite some time. There is just something so eery and fun at the same time about abandoned locations - maybe it’s all the colourful graffiti that often covers the walls of abandoned places, or the bursts of light that come through the broken windows and cracks in the ceilings, but whatever it is, we saw the potential of creating some epic shots in an abandoned place.
Oh how we missed shooting! How we missed meeting our couples! It’s so good to be back, and there was no better way to restart the wedding season than with a romantic Prince Edward County engagement shoot featuring the cutest couple, Emily and Jon…