Last issue I featured Cray Hamilton, the leading vote-getter in the Best Dressed category of the yearbook. This issue I will be reporting on the two other winners of the award, Riley Bosca and Clara Wolff. Usually there are only two representatives for any given Hall of Fame category, but Bosca and Wolff tied in votes. The tie meant that each would receive the honor of Best Dressed in the 2016 Cleveland Legend.

Both Bosca and Wolff were caught off guard when they heard they had been elected Best Dressed. Wolff’s initial reaction was “slight surprise, although I did know a number of people who had voted for me,” she said. Hall of Fame honors hadn’t even crossed Bosca’s mind throughout the week, and she was shocked when she learned she had won.

Despite garnering the exact same amount of votes, Bosca and Wolff have different styles. Bosca says her friends describe her style as “a ‘90s mom,” while Wolff has been told she dresses akin to “a Sri Lankan grandpa.” Wolff believes that her environment cultivated her success in the Hall of Fame. “I am pretty sure if I didn’t go to school in Portland, I would not have been voted best dressed. I like to dress a little differently and I feel that Portland is a place where you can really do that,” she said.

Even if the two winners have a differing sense of what to wear, they both developed a taste for fashion in middle school. “Before sixth grade I could care less what I wore,” said Bosca, “but I would see other people get picked on [for their] sense of fashion, and my clothes were pointed out as unfashionable. So I began to go to the mall and really look at the clothes I was buying: ‘Were they in style,’ ‘Did they look good on me?’ While my sudden focus on fashion was initially brought about negatively, I found that I really loved fashion. I loved expressing my mood and personal aesthetic with my clothing.”

Both Bosca and Wolff enjoy thrift shopping, and each cited Buffalo Exchange as one of their favorite places to shop.

While Bosca and Wolff may dress as if they are older souls, both will be remembered for their sense of fashion while in high school. Each will be cemented in Cleveland history as a best dressed winner in the Legend.