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How did first-year student (and former tomboy) Anna Cunningham end up writing a fashion column online?

U of T student and fashion blogger Anna Cunningham was once a self-proclaimed tomboy who dressed exclusively in boys’ clothing. In the 10th grade, however, she discovered the world of haute couture. “I began casually reading about fashion, and then started a ‘look book’ on my computer,” she says. She wrote her first fashion blog in Grade 12.

Recently, the first-year student secured an internship with College Fashion, a website with a weekly readership of more than 100,000 college and university students.

After stumbling across College Fashion and becoming a loyal reader last year, Cunningham entered a contest to become an intern at the site. She was offered a six-month position in January, largely based on the content of her blog, Hurricanes and Jellybeans; she is now writing the site’s weekly “Would You Wear” column.

Cunningham primarily writes about fashion, trends, art and photography. While some bloggers strive to gain the largest readership possible, Cunningham writes mostly to discover things about herself. “If nobody read my blog, I would still enjoy doing it,” she says.

Who is her favourite designer? Cunningham admires Sonia Rykiel, 80, of France, whose shows commonly feature oversized sequined berets or long, clinging sweaters. “It’s so much like playing dress-up. That’s what I really enjoy,” Cunningham says. “Half the fun in fashion is not taking it too seriously, because it can make you feel whimsical, like a little kid again.” She also counts Audrey Hepburn and the young Marilyn Monroe as fashion heroes. “Before the blonde hair,” Cunningham specifies, “Marilyn was so understated, and real and charming. We don’t have that anymore.”

Fashion designers may not be solving the world’s problems, but fashion serves a valuable societal role nonetheless, says Cunningham. “Fashion is what you’re showing to the world, but it’s also what you put on for yourself,” she says. “It would be great if I could say that nobody judges anyone by what they wear, but sometimes it’s the only thing people see.” Fashion is a way to communicate something about ourselves, to put a little bit of who we are on the inside, on the outside, she adds.

Cunningham thought she wanted a career in academia, but now she isn’t certain. Writing for the Varsity newspaper and for College Fashion has opened her eyes to the possibility of a career in journalism, perhaps writing book reviews, film reviews or fashion journalism. “Right now I’m just taking advantage of all the opportunities I can find, and enjoying the experience,” she says.

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