Subscribe for outfit inspiration and tales of adventure

Get the latest and greatest straight to your inbox!

My Dress Shopping Experience

September 3, 2019 9 Comments

Technically, this post shouldn’t even be included in my wedding planning series because I bought my dresseS (yes, plural, there were two) before I even got engaged.

Hear me out – when I went dress shopping, I wasn’t even planning on buying a dress at all. I had intended to wear my grandmother’s wedding dress that my mom also wore on her wedding day. There was the teeny tiny issue of it being a couple inches too small, but I figured I could make it work…

Going dress shopping was just an indulgence for my mom and me, so that we could have the experience together. I knew Azim was going to propose at some point last year (after eight years together, he wasn’t getting away with waiting any longer), so when Kleinfeld’s had their sample sale, my mom and I made an appointment and headed down to Queen Street.

We sat and flipped through bridal magazines in the waiting room until it was our turn, and then we met our consultant and were brought into the showroom. There were racks upon racks of gorgeous dresses in every style, in various shades of ivory, blush, and white, all organized by price. Because this was a sample sale, many of the dresses were $500!

My mom and I actually split up, but ended up meeting in the middle when we both eyed the same gown at the same time. We both thought it was THE ONE! There was another one that I loved, but it was out of my budget. My mom insisted I try it on anyway, just for fun. We added a few more to the pile, but I was pretty set. My mom and I have that in common – we are very decisive and can make our minds up easily 🙂

We went into our swanky fitting room, and our consultant helped me get into the first dress, the one my mom and I both loved. It was a huge Disney princess style gown with a long train, a light blush tone, with a sheer collar, tuxedo band, and little jewel buttons. It was so unconventional, so over the top, so very me.

The reception gown
I don’t have professional photos of this one back yet…
But how dreamy was it for our First Dance!

The moment I stepped into it, my mom and I made eye contact – this was IT. This was THE ONE! The best part? It was off the $500 rack. My consultant happily told me that the dress had originally been four figures, so it was a huge savings. I said yes to the dress…and then…thought about maybe trying on the other dress I loved too. JUST IN CASE.

Uh oh. The moment I stepped into the other gown I knew that it was THE ONE too! This one was more traditional – a beautiful white lace overlay on top of the most gorgeous, ethereal crepe fabric. A shorter train, but still a dramatic silhouette. It was also me, but in a more classic and timeless way.

“I could buy two dresses…one for the ceremony and one for the reception,” I pondered out loud.

“You could…” my mom said warily.

The consultant’s ears perked up. She knew a big sale was coming her way. Little did she know, the world’s best bargainer was in the room.  My mom began the negotiation, and didn’t stop until the manager was in there with us.

The manager agreed that both dresses were THE ONE, and something had to be done so that I could buy both. Theatrics were involved, conversations about the delicacy of the crepe fabric, the uniqueness of the designs, the designer labels, etc. I wavered back and forth, and my mom deliberated with her until a deal was reached that we were all happy with (but especially me and my mom).

My ceremony gown

And that is how I ended up with two wedding gowns! I did try one more on after I found both of the ONES, just to make extra sure, and it was no contest. The third one I tried on just sort of fell flat, even though it was just as beautiful as the other two. I guess what they say is true – when you know, you know!

As for my grandmother’s wedding dress – a solution was reached. I still wanted to incorporate it into my wedding somehow, so I decided to wear it for my engagement photos. I wanted to take a photo similar to my grandma’s and my mom’s, and then put all three into a triptych frame for her birthday.

The photos turned out beautifully, and I think this way worked out much better. My grandmother’s dress is absolutely gorgeous, but it is also a heavy fabric with long sleeves and a high neck. If I had worn it on my wedding day I would have been sweating buckets!

I’m so glad I have the photos to honour her. Azim also wore a double-breasted suit to try and match what my grandpa was wearing, and my mom made the gorgeous bouquet from Lily of the Valley from her garden.

I am so happy with my dresses and the experience I had! I know it’s not the typical experience, but I’ll still offer some tips that I found helpful:

1. Come prepared

You may not have your wedding shoes yet, but it’s helpful if you at least know the approximate height of the shoes you’ll be wearing so you have an idea of what alterations are necessary.

Also, make sure you wear a nude bra, underwear, and bring your shapewear if you’re planning on wearing it! I ended up not needing a bra or shapewear because my dresses had a built in foundation. But if you’re planning on wearing a mermaid style or fitted design, the right shapewear can make all the difference in fit – more on this when I share my engagement photos!

2. Buy a dress that fits you now

I’m so glad I didn’t buy my dresses with aspirations to lose inches and squeeze into gowns I’d be uncomfortable in. I felt totally confident the day I bought them, and completely comfortable on my wedding day. I recently read this article and loved it. This is a deeper issue that I feel strongly about, but for the sake of this article I’ll just say – buy a dress that fits.

3. Have an open mind

You may have pinned a hundred images of ball gowns, only to realize that they don’t look as perfect on as you imagined. Instead, a strapless sheath might wow you, or a bell-sleeved bohemian design might blow your mind 🙂 Narrowing your options down to one specific expectation may lead to disappointment.

I was certain that I would end up in a dress with sleeves – the closer to Kate, the better. But I ended up with shoulder-baring gowns I wouldn’t even have dreamed of – and I’m so glad I did.

4. Trust your gut

When you find THE ONE, you’ll know. It will be the dress you don’t want to take off, and you won’t need to rely on anyone’s opinion but your own. If you’re constantly asking those around you for reassurance (I’ve seen women post photos in a forum with 10,000+ members to ask for opinions)…it’s probably not the dress for you.

If you were a bride who has had a great or even not so great experience with dress shopping, I’d love to hear about it! Please share any tips or advice in the comments below 🙂

As always, thank you so much for reading xox


All posts


  • Nabila Islam September 3, 2019 at 10:25 am

    Ahhh congratulations again! You looks beautiful! I’m so happy your mom was able to bargain down the price of the second dress so you could get both. And I hope when you do the engagement photo post that you show us the triptych because that would be lovely!

    I went to several places for my dress for next year (we did a civil ceremony this year and celebrated with all our friends and some extended family, but next year plan to do a destination with a much smaller group). I went with friends each time to search for my dress, usually 1-3 women. But the day I went to try on a dress alone, I knew it was the one for me. It wasn’t like any of the dresses I had been trying on, all of which were beautiful on and off my body, but none of which I felt were the one I should spend my money on. No one knows what this dress looks like, and I plan on keeping it that way until the wedding!
    I also agree, that it’s nice to have an idea of what you want to try, but don’t be so set that you don’t try ones you dont think you’ll like. Especially the first dress shopping stop. You don’t know what you’ll like until you try on the different styles. I really wanted a beautiful, soft lace dress. But that is not what I got at all!

    Looking forward to the rest of the wedding series! Keep up the great posts!

  • Lillian September 3, 2019 at 1:03 pm

    I am so grateful you took me along dress shopping and included me all along the way. You had my dream wedding.
    Loved loved our shopping experience.

  • Connie September 4, 2019 at 12:00 pm

    Absolutely stunning…all of them! ♥️

    • jocelyncaithness September 4, 2019 at 6:41 pm

      Thank you <3!!

  • Agnes September 4, 2019 at 6:19 pm

    Thanks for sharing.. you look gorgeous in all the gowns

    • jocelyncaithness September 4, 2019 at 6:41 pm

      Thank you so much <3

  • […] be posting my wedding series in chronological order – I started with my wedding dress shopping experience, because I bought my gowns before I got engaged […]

  • Hanan September 9, 2019 at 7:42 am

    You looked so gorgeous in both of them!!! Loving this series

  • My Engagement Photos – Jocelyn Caithness September 24, 2019 at 11:52 pm

    […] 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 […]

  • Leave a Reply

    I accept the Privacy Policy * for Click to select the duration you give consent until.

    This site uses Akismet to reduce spam. Learn how your comment data is processed.

    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

    Subscribe for outfit inspiration and tales of adventure

    Get the latest and greatest straight to your inbox!

    The Archives