Jonathan Crosson

Robert Geller may be better known for his utilitarian, post-industrial clothing, but these “David” frames prove the New York-based designer knows his way around a pair of glasses as well. Handmade in Japan from a hard-to-find Japanese-resin, the stark black frames are a modern and military-inspired take on the classic wayfarer style. Geller turns the design on its hinges with a bold and blocky silhouette, creating winged-out temples and a slightly jagged dip at the top of nose bridge.

Jonathan, who we photographed in Toronto, liked the polished look of the frames and the matte black colorway. The glasses are big enough to stand out, while still maintaining a cool and casual quality, working with a number of looks and face shapes.

Kyle Kofsky

Here’s an interesting story about Kyle’s pair of Ray-Bans: he bought them in 1993 at Lenscrafters and they were originally supposed to be sunglasses but the store messed up on the tint. Kyle liked them so much, he kept them anyway, and has worn them as optical frames ever since.

The rimless frames, aviator lenses and double wire bridge are all signatures of 90s eyewear design, yet these glasses still resonate as a cool, suave pair of specs today. Kyle told us that every other pair of glasses that he’s bought since 1993 have broken. In style and in durability, this pair has stood the test of time.

Richa Watts

Richa got these “Brunel” frames for 25 pounds through Specsavers in the UK. They reminded him of a pair of glasses his friend used to own – notable because Richa always remembered his friend by his glasses, and because he was able to get the same look but at an affordable price.

This pair of two-tone frames feature a brown and honey combo that is mirrored at the temples: the temple tips end in the same honey colour as the front of the frames. The oval-shape of these glasses is ideal for narrower faces, and adds visual interest without being overwhelming. The plastic frames are finished off with Pentax lenses.

Lauren Michaels

We spotted Lauren on her way home from a picnic in the park in these “blond tortoise” Celine sunglasses. Lauren loved the exaggerated teacup-shaped frame, which adds extra glamour to these celeb-worthy shades. Made from acetate, the frames feature a classic keyhole bridge and silver, pin-dot detailing on the sides. The Céline logo is printed on the temple. The glasses are fun yet luxurious, versatile enough for a casual day at the park like Lauren, or for a big night out on the town.

Yazmany Arboleda

We spotted New York-based artist Yazmany Arboleda in these Paul Smith “Chaucer” sunglasses. Made from a mix of plastic and glass, these vintage-inspired shades feature a classic keyhole bridge, P3 lens shape and “crystal” frames. The purple tint is more unique than the traditional brown or black gradient lenses, and we love how it contrasts with the transparent frames. The outside right temple tip features the Paul Smith signature logo, while a ‘Cherish The Day’ quote in Paul’s handwriting is imprinted on the temple-tip interior. We also love the shape of these frames – not too small but not too large, fitting comfortably between fashion and function.

Sharlan Cuffy

Sharlan’s Yves Saint Laurent glasses are big, bold and quirky – just like her personality. Fitting, since she wanted a pair of frames that people would notice. These unisex frames are made from acetate, and feature an oversized rectangular frame with chunky arms. The glossy finish of the front is juxtaposed with the matte finish of the arms. An embossed golden Yves Saint Laurent logo sits just below the temples, adding a touch of luxury to the otherwise simple pair of frames.

Zeke Goodwin

Zeke Goodwin is a trained chef who just made the move to Toronto to work in TV. What better way to mark the occasion than with a new pair of frames? These Japanese-inspired glasses are from popular discount retailer Optical Thirty 8. Made from wood and acetate, the frames are a slightly larger take on the classic square-shape, and fit perfectly on Zeke’s face. We love the contrast between the brown and black, and between the grain of the wood with the smooth finish of the acetate.

Zeke thought the wood felt “very Toronto” and would help give him a new, hip look in the city. We think he’ll fit in just fine!

Corey Wiseberg

These may look like a regular pair of shades, but Corey’s black Vilebrequin sunglasses are actually made from a rubberized material that’s not only super flexible, but buoyant as well! Yes, these glasses can bend and float!

Best known for their swim trunks, Vilebrequin first introduced a line of rubber sunglasses two years ago, and they’ve been released in varying shades and small quantities ever since. Corey bought his pair in Rome and likes the fact that no one else really has them. In addition to the TPU frames (Thermo Plastic Polyurethane), the lenses are made from a scratch resistant, recyclable material, manufactured through a sustainable, eco-friendly process. A raised Vilebrequin logo sits on the side of the arms.

The best part: these stylish shades capture the carefree feeling of the coast, while being practical enough to actually take a dip in the water!

Lauren Backman

Lauren’s Louis Vuitton aviators are perfect for her face shape, while lending a touch of elegance to her casual, everyday look. These glasses feature some incredible detailing, with the signature “LV” logo running down the side of the temples and along the inside of the frame. And we love how the golden finish looks with the brown gradient lenses.

If you have a smaller face like Lauren’s, aviators are a flattering choice of eyewear. The flat-top bar and rounded lenses are a great way to add some angles and dimension, without going over the top. Plus you can’t go wrong with a cool and classic pair of sunglasses!