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My Engagement Photos

September 24, 2019 5 Comments

Today I’m sharing my engagement photos, the four main factors that made the photography session a success, and the one thing I wish I’d done differently. I’ll touch on the significance of both of my outfits, and why these pictures are so special to me.

The main reason why these photos turned out so beautifully, is obviously, the superstar photographer. I’ll be including more about Rachel Keyes in my upcoming post about my vendors, but sharing my engagement photos is the perfect opportunity to highlight just how incredible she is! Having a good photographer was probably THE most important part of my wedding planning, and Rachel exceeded all my expectations.

I think the best part about working with Rachel is how professional, kind, and patient she is. She really is just one of the loveliest humans I’ve ever met! She managed to capture the best of both me and Azim, without us feeling awkward or like we had to try hard to look “lovey-dovey” 🙂 She made the experience a lot of fun.

The second success factor, and an underrated accessory that I want to shout about from the rooftops, was my shapewear. I knew that neither of my dresses would be forgiving once zipped (think: not being able to eat or sit down without displacing an organ), and I wanted some help to smooooth everything out. I knew these pictures would be around forever, and I needed to seek help from someone who could really sort me out – so of course, I made my way over to Lida from Inside Story Lingerie. I’ve written about Inside Story before, and what an incredible experience I had getting fitted. Truly life-changing. All my tops fit me better when I’m wearing the sets I bought from Inside Story!

I visited Lida’s beautifully renovated shop in Oakville, and brought my tightest dress with me. I had tried on the cheap shapewear I’d had stashed in the back of my underwear drawer from Winners, and it definitely wasn’t cutting it. Lida showed me several options – at several price points – and explained the benefits of one style vs. another. She was really patient, and wanted to make sure I got a style I’d be comfortable in, but which was also up to the task of giving me the confidence I needed to strut my stuff in my dresses – without bursting a seam. I ended up going with a style from Janira. I’ve worn it MULTIPLE times since. It’s easy to wash, has held up well (literally), and has now become my go-to.

A bonus of my trip to Inside Story was walking away with the BEST strapless bra! I knew I’d need to invest in one for my cheongsam (Chinese outfit), as well as the dress I wore to my bridal shower.  And really, every woman should have a good strapless bra. I don’t know about you, but before I found my perfect strapless bra, my options when faced with a tricky neckline were usually:

Go braless. Embrace my inner 70s goddess. Free the nipple… Start to wonder if people are staring at my liberated nipples through my top. Wonder why it’s so cold all of a sudden. Cross arms at every chance. Contemplate buying a scarf? Curse myself for feeling insecure. Curse myself for not just wearing a damn strapless bra.


Wear the ill-fitting strapless bra I’d bought at a generic lingerie store that will remain nameless. Become annoyed at having to continuously pull it up. Notice that it’s creating a weird line under my shirt, like my boobs are a shelf. Wonder why I decided to wear a strapless bra.


Pull garment with tricky neckline out of closet. Remember two scenarios above. Put garment with tricky neckline back in closet.

Well, I no longer have to worry about that! I LOVE my strapless bra from Wacoal. Again, Lida provided me with several options, at several price points, and gauged what was really important to me in a strapless bra (comfort and staying power). This bra comes with straps, so it’s a great workhorse. It’s super comfortable, and it completely changed the shape of my dress on my body. This exact bra may not work for you, but I highly, highly recommend getting fitted by a professional like Lida and the rest of the staff at Inside Story.

My third success factor was booking my wedding makeup trial on the same day as my engagement photos. This was helpful because I knew I’d look done up and glamorous for the photo session, and it would also give me the chance to see how my wedding day makeup would look on camera (and adjust if necessary). I am SO glad I did this – definitely something I would recommend to future brides to try, it just takes a lot of planning in advance to get dates to line up.

The last thing I want to mention is doing research on photo locations. This seems obvious, but one thing that many people don’t realize is just how many spots in Toronto require a permit (aka $$$). I knew I wanted our photos to have a “city” feel vs. “outdoorsy”, and this narrowed down my choices even further.

We ended up doing our photos at Osgoode Hall – perhaps one of the only traditionally picturesque locations downtown that doesn’t require a permit. We went at sunset and I was expecting many other couples, but we were pretty much alone! There was only one other couple, and they left pretty soon after we arrived. I think it was because we chose a Sunday evening…or maybe we just got lucky! In any case, I love how well our location complemented our outfits. It was all around perfect 🙂

The one thing I wish I had done differently, was schedule a hair appointment. This is pretty much a non-issue for a lot of brides who opt to go for a more casual look in their engagement photos, but that’s not my style 🙂

I thought I could do an updo myself…but on the day of, realized I was badly mistaken. I ended up getting a last-minute appointment at Blo, and asked for a loose bun/updo. I’m happy with how it turned out – it’s definitely more effortless than my wedding updo (not a hair was out of place from 7am til 2am). But I was SO stressed trying to get from my makeup appointment to hair, to the photo location. So be prepared, and try your look out beforehand as completely as you can so there are no unexpected surprises or disappointments on the day of!

The significance of my two dresses:

I knew I wouldn’t be incorporating the customary Chinese wedding traditions into my wedding, so I really wanted to honour my heritage by wearing a cheongsam. I wanted my grandparents to have these photos, and see something familiar and nostalgic when they looked at them. The red was striking on camera, and looked SO good with Azim’s suit 🙂

I also wanted to incorporate my grandmother’s wedding gown into my special day. Not only did my grandmother wear it, but my mom did too. I wrote about my wedding dress experience in this post, which explains why I ended up with two of my own gowns – but I knew I could pay tribute to my grandma by wearing her gown in my photos.

Rachel actually helped me recreate the photos, and captured the look perfectly. Azim tried to match what my grandpa was wearing, with a double-breasted jacket and lighter-hued dress pants. He looked very handsome 🙂 I know if my grandpa were here, he’d say the same thing.

I hope you enjoyed these photos, and a little peek into my engagement photo session experience! As always, thank you so much for reading xox


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  • lillian September 25, 2019 at 7:31 am

    Another beautiful post. You are truly the most thoughtful person. You thought of everybody.
    As usual you look AMAZIN.

  • Hanan September 25, 2019 at 9:01 am

    I love your you incorporated both Grandma’s into this shoot! You look stunning!

    • jocelyncaithness September 30, 2019 at 10:11 pm

      <3 <3

  • Nabila Islam October 4, 2019 at 11:16 am

    You both look amazing, and you’re right the red of the chenogsam really pops!
    I love that you incorporated both sets of grandparents and heritage with your engagement photos. It’s very sweet and beautiful. And thank you for sharing some photos of your lovely mother and grandmother from their wedding day. All of you look beautiful in the dress!

  • A look back at 2019 – Jocelyn Caithness January 1, 2020 at 9:44 pm

    […] marked the start of the busiest summer of my life. In this month alone I managed to pack in our engagement photoshoot, my bridal shower, a truly astonishing number of job interviews, and a trip to Sweden to attend our […]

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    About Me

    About Me

    Hi, Friend!

    I'm Jocelyn: a daydreamer and fashion lover disguised as a finance professional. My head may be in the clouds, but my stilettos are firmly planted on the ground ;)

    Jocelyn Caithness

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