How To: Rock Your Engagement Shoot

Mention an engagement shoot and most will roll their eyes. I blame Pinterest and wedding blogs for this one – e-shoots can be incredibly twee to the point of a visceral, disgusted reaction. I get it. When they’re bad, they’re really bad. Last week, after nearly a full year of being engaged, we finally took our engagement photos at the Distillery District and a second downtown location.  Shockingly, we had the best time (more on that in another post!). To prepare, I reached out to our photographer, Mike Caringi from 5ive15ifteen photo company and Toronto image Consultant Christie Ressel for some tips & tricks. Find out how to rock your own e-shoot below!

5 tips for perfect engagement photos - Toronto wedding photographer Mike Caringi

Why do an engagement shoot?

Booking an engagement shoot is actually a really practical thing to do. Yes, a photoshoot dedicated to the sole purpose of taking romantic photos is practical. Really! Along with providing you with beautiful professional photos that you can choose to use for the wedding or even gift to your excited family (OK, probably just Nonna), an engagement shoot provides an opportunity to get to connect with your photographer and get comfortable in front of the camera pre-wedding.

The original "Engagement Photo" from the day after!
The original “Engagement Photo” from the day after!

“An engagement shoot allows us to bond with our clients before the big day and to gain a sense of comfort with one another. It also helps us to learn what works for the couple and gauge how much (or how little) direction they need to look good and feel comfortable” – Mike Caringi, 5ive15ifteen photo company

I’ve been taking great care in choosing all of our wedding vendors, so I had no doubts that Mike Caringi was the right guy for the job but I will say that our engagement shoot cemented it. The rapport we developed with Mike leading up to and during the shoot has made us both incredibly comfortable and excited for the wedding day. My photo-hating fiance can’t wait to see our shots from the day and hasn’t stopped singing Caringi’s praises.

Location, location, location

As soon as you decide to take the engagement shoot plunge, anxiety over location will likely set in: the options are literally endless! Caringi suggests thinking of a location that might have some significance for you as a couple – consider revisiting where you had your first kiss, where the proposal happened, your favourite restaurant. If you’re still drawing a blank, ask your photographer for suggestions! They probably know some great spots around the city.

Distillery District Toronto love wall

Mike and I decided on Distillery because we took our first photo as a couple there during Nuit Blanche in 2010. Caringi suggested a nearby street with great sunset views for our secondary location, someplace Mike & I never would have thought to go! Try to be openminded and also remember that some locations may have photo permit fees associated with them.

What to wear

My first real Bridezilla moment came the week before our engagement shoot. My bridesmaid + oldest friend Jaime sat on my bed and watched me empty my closet for hours. The one dress I loved? It had a permanent stain! Cue anxiety-ridden freakouts to my coworkers (Gillian, Vanessa + Linda, you each get a gold star), lunchtime visits to Holt Renfrew and Rent Frock Repeat and cold sweats. In the end, Caringi saved the day with the offer of photoshop and I was able to wear the stained emerald green dress of my dreams. My wardrobe woes have a moral, though. Wear something classic, wear something you feel and look great in and wear something that fits!

 When selecting an outfit, I suggest that couples select looks that have classic elements to them. While trends are fun, you don’t want to look back at your clothing choices 15 years from now and say, “What was I thinking?” – Christie Ressel, Personal Power Image Consulting

Caringi suggests solid colours where possible and co-ordinating – not matching – your partner. Always think about where you’re going to be shooting as well and wear something location-appropriate. Considering a wardrobe change? Do it! Ressel suggests 2-3 looks so you can switch things up. I slipped on a second dress and Mike swapped his button down for a tee at our second location and I’m so glad we did – it almost feels like we got two separate shoots in one! One last thing: don’t forget to use this opportunity for a hair & makeup trial! It’s a great opportunity to see how your artists translate your vision on camera.

Engagement shoot tips & tricks

What about that themed shoot I saw on Pinterest?

Say it with me: Pinterest = unrealistic expectations. It can be so hard to convince yourself that a “regular” engagement shoot will do when there are so many beautifully styled options all over the Internet. Rainy makeouts a la Notebook! A twee retro picnic! Frolicking through a meadow/in a forest with an artfully arranged bouquet of peonies while wearing a tutu! [real talk: I considered all of these things. Check out my vintage engagement shoot Pinterest board.]

“Unless you and your fiancée are huge Star Wars fans and met an the annual convention in your city…leave your light-saber and costumes at home.”   – Mike Caringi


When it comes down to it, themed photoshoots can be great if they tell a story about the couple but there is always the caveat that you will probably want timeless photos you’ll love down the road. You also don’t want the theme to take away from the true focus of the photos: you and your fiance! Instead of being overly thematic, Mike and I chose to focus on something we both love in a meaningful way. We used his vintage Mercedes convertible as a prop and did a bit of a retro-inspired shoot. And yes, we took both the Marilyn & Joe and Reese & Ryan photos from my board. We’re cool like that.

This still feels like it’s going to be awkward.

Let’s be honest: it might be awkward for awhile. You’re balancing a few conflicting things: you want to look candid but also awesome and also want to convey your love for your partner. It’s possible to combine a flattering angle, romance and those quick romantic glances. My best advice? Listen to your photographer! They know what they’re doing and will give you gentle direction while allowing you to do your thing. If all else fails, there’s always bubbles & beer – Caringi’s secret weapon.

Distillery District Engagement Shoot


I’ll be sharing a peek at our engagement shoot in the coming weeks, but for now the pic above will have to tide you over.


What advice do you have for a seamless engagement shoot?