Real Weddings: Kate and Matt

Inside a laid-back bash at Drake One Fifty

Kate Chippindale, Wealthsimple’s partnerships manager, and Matt Ravenscroft, head chef at Rosalinda, met back in the spring of 2016, when they were both working at the Drake Hotel. Matt had just come on as the catering chef, and Kate was immediately attracted to his confidence. She started strategically bumping into him at the Drake’s properties, and they developed a friendship. Matt wasn’t aware she had a crush and assumed it was coincidence that kept bringing them together. After being tipped off by a mutual friend, Matt finally asked her out to dinner at Superpoint in the fall—and they haven’t spent many nights apart since.

After a year of dating, Matt proposed one Sunday morning in their Dovercourt home. The proposal was simple and heartfelt, and they wanted to bring a similarly unfussy vibe to their wedding day. “We wanted lots of dancing, great food and everyone to have a cocktail in hand as soon as they walked in,” says Matt. Though they’ve both moved on to other jobs, they chose to host the celebration at Drake One Fifty as an ode to their relationship history (the massive 360-degree bar didn’t hurt, either). Here’s what went down.

Cheat sheet

Date: September 28, 2019
Photographer: Kayla Rocca
Bride’s attire: Jacquemus; A La Robe
Groom’s attire: August and Ashley
Hair and makeup: Sandi White Studio; Hayley Bogaert
Venue: Drake One Fifty
Dessert: The Cheese Boutique
Music: Sam Polley and the Old Tomorrows; Karim Olen Ash
Flowers: Timberlost
Invites and stationery: Tori Chippindale
Favours: Mom Jeans Provisions
Guests: 190

The morning of the wedding, Kate got ready with her mom and sisters at Sandi White Studio, and Matt had lunch with his groomsmen at Bar Raval. Then they had their first look at East Room:


Kate knew she didn’t want to wear a traditional wedding dress, and ended up finding a style she loved at the Room. The Jacquemus dress was yellow and far too big, but she was able to find a cream version online (and at a discount to boot). Matt got his three-piece suit custom-made by his friend Dirty Sox. They jazzed it up with a pink floral lining and personal touches, like an inscription of the wedding date inside the lapel:


They had a drink and some snacks at East Room with their families before heading over to the venue:


Drake Mini Bar, in the same building as their venue, served as a pseudo green room for the party. Kate waited there before the ceremony while Matt greeted guests at Drake One Fifty. The stationery was made by Kate’s sister, Tori:


As expected, everyone had a drink in hand when it was time for the ceremony. All the florals were done by their friend Lauren Wilson of Timberlost Designs. Aside from showing her a picture of her dress, Kate gave her no other instructions. “I wanted the day to be an opportunity for my creative friends to express themselves,” she says:


Inside the venue, they kept the decor simple. “Drake One Fifty has a lot going on already,” says Kate:


Lauren also designed the whimsical floral installation surrounding the altar. “One of my favourite moments of the day was walking in and seeing what she made. It blew my mind,” says Kate:


The couple held a short, informal ceremony officiated by Kate’s godmother and Matt’s uncle. They wrote their own vows:


The couple worked with the Drake on a menu of passed bites and food stations. There was Waygu striploin, house-cured charcuterie, smoked sablefish, venison tartare and Acadian sturgeon caviar. Their friend Afrim Pristine of the Cheese Boutique gave them a four-tier cake made entirely of cheese, and for favours, they handed out custom cookies infused with TCH and CBD from Mom Jeans Provisions:


Their band was Sam Polley and the Old Tomorrows (Sam is Kate’s sister’s boyfriend), who played lots of upbeat rock and fun covers. They alternated the band with a DJ, Karim Olen Ash:


Their first dance was to Van Morrison’s “Into the Mystic.” By this point, Kate had changed into her second outfit, a slip dress and Converse sneakers:


Sam Polley’s dad is Jim Cuddy, lead singer of Blue Rodeo. For the groom’s dance with his mother, they projected a video tribute from Cuddy himself (Matt’s mom is massive fan):


It was well-received:


Guests gathered around for speeches:


And from then on the evening was mostly a giant dance party:


Guests of all ages were tearing it up:


Here are some more images from the evening:


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