Gideon Dunns

We spotted Gideon at the MoMA Store in New York wearing these super limited-edition Prada SPR 25PS “Poeme” glasses. Originally designed as sunglasses, Gideon swapped the black gradient lenses for optical ones, which add to the intriguing look. Handmade in Italy, these acetate frames feature an in-your-face design, with a bold square shape and hand-painted flowers on the browline and temples. The frames exude lightness, nobility and amusement all at once. Produced for Prada’s spring/summer 2013 collection, these glasses almost immediately sold out and are considered extremely rare. They were the most whimsical pair of frames Gideon could find that told a story. “When you need optical frames, it’s hard to make a statement without being too crazy,” he told us. “These nailed it!”

Kareem Malek

Kareem owns a lot of circular glasses, including a pair of Oliver Peoples’ frames and a pair of matte black LGR frames. He picked up these circular Prada sunglasses recently, after being on the hunt for something metallic. Made in Italy, these rounded, aviator-style frames feature smaller lenses and a curved double bridge, which mirrors the natural arch of Kareem’s eyebrows. Nose pads help the glasses sit perfectly on his face. Seen in a “silver demi shiny” colour way, the retro-styling of this “PR69OS” model is similar to the sunglasses worn by Jamie Foxx in the movie, Django Unchained. While those ones were custom made for the film, these Prada shades are just as cool, and a worthy new addition to Kareem’s collection.

Kyle Joe

Kyle Joe is the Senior Digital Producer at MuchMusic, and we spotted him on a break from work at Osheaga. Kyle picked up these Prada frames from Charles De Gaulle Airport during a layover in Paris, because he was a) bored and b) “wanted to up his eyewear game.” Mission accomplished.

Often seen with suits or dressed-up denim for a night on the town, these tortoiseshell sunglasses are given a youthful new spin paired with Kyle’s sporty, festival-ready outfit. The sophisticated shades work equally as well on a more casual look, and Kyle pulls off this high-low mix perfectly. We love the unique details on the glasses, like the not-quite-rounded lens shape, the curved temples and the double-bridge. Judging from the rest of his outfit, it’s clear Kyle appreciates the little details as well.

Jennifer Chun

Jennifer had just purchased these Prada sunglasses in Seattle the week before we snapped her photo in Toronto. These glasses are classic Prada: sexy and feminine with just a hint of mystery. The curves on the frame are strong and sophisticated, and the detailing on the corners of the temples add an elegant touch. Oversized frames can sometimes veer on the overly-trendy side of things, but when paired with classic stripes and black pants like Jennifer, they’ll never look out of style.

Portia Bartley

“Menswear as womenswear” was a huge trend across many of the major collections for spring, so it would only make sense for the concept to be extended to eyewear. Portia’s Prada glasses are similar to the pair actor Michael Pitt is sporting in the company’s spring/summer 2012 campaign video, but she manages to inject a fun and feminine touch. And while we love the look of these two-toned frames, it’s the wood panels on the temples that really make these glasses stand out.

Mickey Boardman

We told Paper Magazine’s Mickey Boardman that an eyewear site would not be complete without a photograph of him. His reply: “I totally agree.”

Though he has a few pairs of glasses on rotation (among them, a pair from Coach and a pair of Selima Optique “Arni” frames), Mickey’s been favoring this pair recently – oversized women’s sunglasses from Prada that he turned into prescription frames.