The 27-year-old American baseball player (and honourary Torontonian) has been dubbed one of the most stylish people in the 6ix, alongside rapper Kardinall Offishall, eTalk host Liz Trinnear and Kiss 92.5 and ET Canada's Roz Weston, his partner, Katherine Holland, and their daughter, Roxy Alabama.
According to Toronto Life, Pillar is an "undercover cowboy" who owns "multiple pairs of cowboy boots" which he wears anytime he goes to Texas or Kansas City. He also takes great pride in his grooming, only allowing Josh Diamante at Throne Barbershop to cut his hair during the season.
For the rest of this year's Toronto Life Best Dressed winners, head to torontolife.com.
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