Stephanie Ray was a law student competing for internships when she realized she might not be meant for the profession’s conservative wardrobe. “I would interview and be holding my jacket and put it on at the very last second because I didn’t feel good in it,” she says. Despite having zero design experience, Ray seized upon her need for fresher, more versatile pieces and Grayes was born. She moved back to Toronto after law school and began gathering the information and expertise required to start her own fashion line. “It was definitely a risk, but I knew it was the right decision,” she says. Grayes was formed in 2016 with a few basic wardrobe staples, like tapered pencil pants and the sharply tailored blazer dress, offered only in black. This year she has branched further into patterns and textures, adding neutral plaids, greys, lace and even camouflage to the classic pinstripes the brand introduced shortly after launching. The pieces are still conservative—skirt hemlines are generous, and jackets offer plenty of coverage—but they have a distinctly youthful and sharper feel than the traditional Clinton-esque pantsuits of yore. The highest compliment Ray receives is when women tell her they wear their Grayes workwear pieces off duty. It turns out that a wardrobe staple is just that, no matter what day of the week it is.