The idea of a career in tattooing had never crossed Jenna Crook's mind until one night in 2014. After meeting a new friend on Toronto Island, she noticed the incredible level of detail of her self-applied tattoos — and something clicked.

"I grew up thinking of tattoos essentially as one style of art — one I didn't personally like, so I paid little attention to it," says Crook. "I got my first tattoo from [them] that week, and the week after that I started tattooing myself. I was obsessed."

Crook later purchased her first tattooing machine and ventured somewhere she never expected: she became a full-time tattoo artist. Her designs move away from the traditional idea of what makes a tattoo "good," using a messier and more carefree style.

This new style of tattoo design has gained popularity in Montreal and Toronto, particularly with Gen Z. It challenges the past and rejects the "rigid standards and ideals" of the tattoo scene, bringing an unorthodox and freer form of tattoo design. Crook is one of many artists pushing the fold and creating a space for a new style to enter the scene.

Known online as notcoolneverwas, she plays with the classicism of American traditional in her own distinctive way by utilizing sketch-like designs and playing with the obscurity of images through shading and disproportionate line work. Her tattoos have gained her more than 45k followers on Instagram.

"Instagram in particular… gave access to a free image-based marketing platform and a worldwide audience," she says. "As far as style, I think a lot of the 'newer' styles we've seen enter tattooing are things we've already seen in the art [and] design world for years."

Crook's work is a playful cross between allowing herself to draw "badly" and letting herself enjoy what she creates. She also uses gothic typography such as Old English and creates illegible text tattoos. Classical paintings, internet ads and even at times a "trash photo" she took on the street have influenced her.

"I play first, obsess later," she says about her process of creating work. "Sometimes I fail, but that's the goal. These days I can play with this even more because I'm less limited by my tattoo abilities."

Montreal-based tattoo artist Emerik, known as dirtyl00ks on Instagram, says the rise in popularity of the messy freeform style of tattooing comes from social media. According to him, the remixing of traditional designs makes clients want to explore a style they're not used to seeing, as messier tattoos emerge from the underground scene.

"Before the arrival of those platforms, there were only a handful of different styles going around that you would have to find through magazines or actually going to the shop to look at the flash on the wall," he says. "Now a lot more people are exposed to it and are interested in getting some work done in those styles because they haven't seen anything similar."

Emerik's tattooing style deconstructs traditionalist designs and typography with their own rough and sketch-like twist — "bathroom stall drawings," as he describes them.

"I want my drawing sheet to look like those fake tattoo sticker sheets I used to have so much fun with as a kid," he says. "I draw and tattoo really fast. My drawings are done on the first shot almost, without the need of the eraser."

While Emerik does some custom work, his work is predominantly flash tattoos, where clients choose from drawings inspired by old logo signage, records or anything that inspires him on a daily basis, including playing with Old West tropes in his work.

"Tattooing has been around forever. A lot of the different styles going around are often remixes of older stuff; we get inspired by the history around us and give it our own touch."

Stepping outside of the norm does bring its fair share of criticism. Emerik says he receives negative comments on Instagram from people that think tattoos need to fit a clean standard with realistic imagery.

"I get a lot of hate from older white men who have been tattooing for a lot of years…taking time out of their day to write mean [comments]," he says. In a recent incident, a tattoo artist in New Jersey mocked his work by making a fake flash sheet in Emerik's style.

"I normally just respond with a nonsense answer that confuses them," says Emerik. "It seems like people don't care for paintings or other art forms [being experimental], but as soon as it's tattoos it's got to follow a certain cleanliness and commercial image."

Crook shares a similar sentiment, saying that artists need to be more accepting of newer styles. "It's always funny to me how close-minded artists can be," says Crook. "As long as a tattoo is done safely and consensually, I don't see why the rest shouldn't be between the tattooer and the client."

Alongside this style, a sharper cyber aesthetic has also gained popularity. While these two styles might seem to contradict each other design-wise, they have consistently been associated with one another because of the way they push for nonconformist aesthetics. Clients who have messier playful tattoos will often have gothic-cyber designs alongside them. What makes people adopt both designs are their shared obscurity and originality that complement one another.

Gothic sigilism is everywhere in Montreal. With its sharp lines, wing-like features and intricate cyber-esque detailing, the style has become a popular subsection of the city's tattoo scene. For artist Céleste Bonnier, who goes by underyourskin_x_ on Instagram, the curvature of the human body plays a huge role in her design work. The Montreal-based artist's style has evolved throughout the years, but she has recently found herself focusing on tribal ornamental designs.

"I think people take it more and more like art on them [rather] than like, a signifier of something they are related to," she says. She attributes this to styles of tattooing that were popular in the 2000s coming back into fashion. Bonnier says the current trend of tattoo designs and styles are inspired by other styles that already exist and are "reshaped."

These designs aren't restricted just to Montreal and Toronto; influential scenes in places like Brussels, Berlin and New York have impacted tattoo trends around the world. For most artists, travelling and going international is a regular part of that job.

"It's a big part of the job if you want it," says Emerik. "I go work in New York, Los Angeles, Toronto pretty often. I've worked in Europe for a while before also; you meet a lot of inspiring artists and new clients."

Chicago-based Rene Shin, known as fancycrotch on Instagram, has tattooed across North America, spending time in both Toronto and Montreal. Shin says that in comparison to Toronto, Montreal's scene has opened doors for more diversity in the style of tattooing.

"I think Toronto is super into detail, like feminine and fine line work," she says. She noticed, after apprenticing in Korea, that a lot of Toronto's influence stemmed from Korean artists' tattooing style. "There are so many artists who do detailed work that have learnt from Korean tattoo artists."

Shin was 20 years old when she kicked off her tattooing career during the pandemic after losing her job. She describes her work as neo-tribal, playing with dark gothic themes, chains and symmetry. Since her work first gained traction, Shin has been booked and travelling from North America to Europe.

Montreal, in Shin's eyes, is more experimental and unconventional. Between the mixture of North American and European influences, it differs majorly from Toronto's style. Emerik shared the same sentiment, emphasizing Toronto's unaffordability.

"The scene in Montreal is a bit more experimental and weird, while Toronto tends to be classic and cleaner," says Emerik. "You can experiment a lot more with art projects, restart over if it doesn't work because you don't have the constant need to hustle to pay your expensive rent."

As these styles continue to hold a strong presence in the Montreal and Toronto tattooing scene, Crook says that because of how cyclical tattoo designs are, she's excited to see what the next generation of artists produce.

"There's always been styles that entered tattooing that were not welcome at first, just as there were in fine art. Newer artists come in challenging and rejecting some of the rigid ideals set before them," says Crook. "I can't wait to see what style the kids bring in years from now."