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Street Style: Nine-to-fivers show off professional looks in the Path

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On winter weekdays, the Financial District’s underground maze is the perfect place for lunching Bay Streeters to flaunt their fashionable office wear, sans parka. Last Friday, in addition to plenty of power suits, we also spotted analysts and accountants taking advantage of casual dress codes in colourful accessories and slick blazer-and-jeans combos. Here, 15 of the most stylish outfits from the Path.

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Dave Moylan Age: 32 Profession: Investment advisor “I try to look professional, but still stylish. I wear whatever makes me feel comfortable and confident.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Loredana Minio Age: 40 Profession: Kleinfeld sales associate “We have to wear all black to work, but I try to make it as funky as possible.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Luke Pelosi Age: 35 Profession: M&A director “My look is Bay Street casual.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Amy Tieu Age: 26 Profession: Finance analyst “I’m not as traditional as many people in my office. I try to bend the rules a bit and buy things I can also wear on the weekend.”

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Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Jessica Burnet Age: 26 Profession: Intermediate fund accountant “I try to look laid-back but still professional. I don’t like to be too fancy.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Arthur Nahas Age: 30 Profession: Lawyer “I love wearing knit ties in the winter. I feel they add a ruggedness to my outfits.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Linda Tao Age: 30 Profession: Payments and innovation specialist “I hate the cookie cutter work outfits, especially in banking. My look is very minimalist and chic. I try to find classic statement pieces and pair them with pops of colour.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: JP Mackay Age: 32 Profession: Real estate investor “I try to keep it simple. I like to be noticed, but also easily forgotten.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Kristina Kempf Age: 29 Profession: HR specialist “I dress very feminine at work, but I have a bullet belt at home that I wear to concerts.”

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Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Michael Yeung Age: 23 Profession: Accountant “My dress code is business casual, but I always wear a suit if I’m meeting clients. At the office it’s more chill—especially on Fridays when we can wear jeans.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Rebecca Greenstein Age: 34 Profession: Emergency veterinarian “Work Rebecca and casual Rebecca are two different people. At work, I don’t wear makeup—I don’t even brush my hair. But on my days off, I transform. I love anything whimsical.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Jahan Kargar Age: 34 Profession: Business development manager “This is all my wife’s doing—she loves shopping and I hate it. We have a quarterly shopping date, where we get it all done in a short, intense spurt.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Ilsa Rahim Age: 43 Profession: Legal assistant “My look is funky. I wear whatever’s easy and comfortable.”

Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Hannah Gilks Age: 25 Profession: Trade assistant “I always shop at J.Crew for work stuff. I have a few outfits that I keep on rotation.”

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Street Style: Nine-to-fivers show off professional looks in the Path
(Image: Jenna Marie Wakani)

Name: Dena Springer Age: 43 Profession: Lawyer “I’m visiting my husband at his office, so I’m very casual. But when I’m working, I’m always in a suit or court attire.”

Jean Grant has been a freelance writer since 2015, covering a range of lifestyle topics like shopping, interiors, wellness and culture for publications like Maclean’s and Toronto Life. She also enjoys working with brands to develop custom content, and shares personal essays through her Substack newsletter, Nobody is Thinking About You.
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