Who: Stefan
Where: Broadway & Virginia
Dressed for: Taking photos
Style Highlights: Stefan channels the classic black on black ensemble, while updating the look with an edgier aesthetic by opting for a fitted leather moto jacket and patent pants. The wide brimmed hat and tall oxford ankle boots add a certain rock n' roll elegance to the look.

Who: Alissa
Where: Broadway & Ellsworth
Dressed for: Lunch with Mom & Sister
Style Highlights: Alissa owns her own vintage clothing shop, so it makes perfect sense that we nearly mistook her for Judy Garland, thoughtfully smoking a cigarette in her floral midi skirt and pale yellow sweater. Her dainty ensemble nails the classic 50's aesthetic, though calculated with a sharp eye for detail by adding quirky vintage accessories like a red pillbox purse and cherry lucite pumps.


Who: Blake
Where: Broadway & Dakota
Dressed for: Coffee with a friend
Style Highlights: Kicking back in a sweatshirt paired against a graphic tee and funky patterned socks, Blake keeps his cool with an earthy palette and gives ol' Indiana Jones a run for his money by rocking a wide brimmed fedora paired with a single feather earring.

Who: Sebastian
Where: Broadway & 1st. Avenue
Dressed for: Tattoo session
Style Highlights: Stepping outside for a smoke break draped in head to toe black, Sebastian adds mystery to his look with a fitted leather jacket and a fringed houndstooth scarf. He keeps his look cool and comfortable with fitted black jeans and high top sneakers.

Who: Jordan
Where: Broadway & Maple
Dressed for: Shopping
Style Highlights: Pairing chunky knits and velvet leggings, Jordan mixes shades of burgundy and dark rose for a look that emulates romanticism with a contrasting edge in her geometric necklace and Doc Marten patent combat boots.

Who: Adrian:
Where: Broadway & 2nd Avenue
Dressed for: Lunch with friends
Style Highlights: Adrian dresses in neutral tones of black with a black splash of olive green, while bringing his look down to earth with a knit beanie and tapestry scarf.

Who: Alexander
Where: 16th Street & Lawerence
Dressed for: Wandering the city streets
Style Highlights: Turning heads in a look that's both grassroots bohemian & punk rock, Alexander makes a statement with his layered look. He's not afraid to speak his mind, mentioning anarchy several times in our conversation, but when words fail his head to toe D.I.Y. patches send the message loud and clear.