Tosca Webb: Dress Up

Tosca Webb, 23, was living in Berlin with her boyfriend, Clay, before they moved to Montreal. Originally from Vancouver, Webb indicated there was a technical reason for leaving Berlin: their visas had expired!

When it came to choosing a new home, it was between Vancouver and Montreal. Since there was “really not a ton going on” in Vancouver, she had friends in Montreal and had heard a lot about its music and art scene, she thought she’d give the city a try and see what happened. However, she was sad to leave Berlin and wasn’t expecting to find a city that she loved so much again.

“I love Montreal ten times more, I think.”

Webb does acknowledge that the two cities are very different—she mentions Berlin’s larger population and expansive communities as a few differences, but notes that the concentrated art community in Montreal is a positive for her.

“[I] see the same people at all the [art] events and everyone is so supportive of each other and willing to collaborate,” said Webb. “There’s no strong undercurrent of competitiveness. It’s very collaborative and supportive and encouraging and inclusive.”

Photo by Mikaela Kautzky

She worked as a nanny for the majority of her stay in Berlin, and briefly at an online e-commerce sustainability fashion start-up and a German daycare where she didn't speak the language. Coupled with watching her boyfriend find success in music—though she was proud of him—all of this made Webb feel isolated in Berlin. Though she was having a lot of fun, she felt directionless.

“I just felt like I needed to scream at all times. I was like, ‘there’s so much inside of me and I’m so inspired and I don’t know how to execute this!’ Like I don’t know how to get it out and I don’t know what to do with it. Just a lot of early twenties angst,” explained Webb.

Her move to Montreal came with a mission to do something with all of her pent up creativity. She has always been passionate about fashion, and appreciates photography—especially film photography—and music. She wanted to do something with all of those things, as well as dance, laugh, and have fun—but didn’t know how. That’s how Dress Up was born.

Photo by Mikaela Kautzky


Webb describes Dress Up as an event initiative to create a space for people to experiment and explore fashion and feel comfortable exploring self-expression, where there’s no room for judgement or pretentiousness.

“I feel like a lot of parties and shows and stuff [I] go to there’s…very much like an undercurrent of people checking each other out and trying to see how they fare next to each other. I just wanted to create a space where it’s just pure love and encouragement and inclusiveness and dancing and fun,” said Webb.

Initially a concept shoot where models would style themselves, Dress Up snowballed into a full-blown event. It first took place at Webb’s friend’s apartment with a small group of friends, trying on clothes and dancing together. Next, Webb rented the Glass Door Gallery and made it a public event, though it was mostly just friends that attended. Next, it took place at Webb’s own apartment, and most recently at Psychic City.

Photo by Betsy-May Smith


Upon arriving at the event, guests are invited to try on various articles of clothing on the racks across the wall. Webb rents all of the clothing from the vintage store where she works, which she has been doing since the beginning, but has only started to sell the clothing on the past two occasions. Everyone’s phone cameras are covered with stickers in order to maximize interaction and remain present in the moment, and each guest coat-checks their “street clothes” so they can fully immerse themselves in the dress up spirit. A make-shift change room is available to try on clothes, or guests can change out in the open if they feel comfortable. Performances by musicians like Cher and Tina Turner, as well as Andy Warhol screen tests, footage from the Chelsea Hotel in the 70’s, and clips from Paris is Burning are projected on a screen without sound, while music plays from a record player.

“It’s just a really great way to combine a lot of different mediums of art,” said Webb. Guests are encouraged to dance, drink (responsibly), and be merry.

Photo by Mikaela Kautzky

The spirit of self-expression and encouragement of the event was inspired and motivated by something Webb witnessed at work. While monitoring the changing rooms one day, she observed “the most beautiful exchange” between friends.

“There was a group of friends, two guys and three girls, who came in. One of the guys brought three skirts into the change room, and he came out in one of the skirts and I could see how uncomfortable and awkward he felt,” she noted. “He was like, ‘guys, I tried the first one on but I don’t know. I don’t think it looks good.’ One by one all of his friends started coming out and they were all like, ‘oh my God, this looks so good on you! You look so good!’ You could see his body language change from being incredibly insecure and uncomfortable to blossoming and checking himself out in the mirror and being like, ‘yeah I do look good!’ I just remember seeing that and being like, ‘I want to recreate that over and over again and I want to give people that opportunity.’ I guess that kind of just made it click.”

Webb credits her friends for much of the success of Dress Up, indicating that the people that have been there from the beginning understand the mission for it and the intent behind it, which has set the tone for everything else.

“I just think that we get so caught up in our everyday struggles and our little mundane routines, [so] Dress Up is a really fun escapism. It’s a place where people can go for a few hours and dance it out and try on clothes and maybe feel better about themselves than they did when they came in,” Webb said.

So when will the next Dress Up event be?

“It’ll be in the New Year, for sure,” said Webb, noting all the hard work that is put into planning this event. “I need to chill after this.”

Photo by Betsy-May Smith

Check out the Dress Up Facebook page and Instagram (@dressupmtl) for more information and updates on future events