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Introducing The Kit's new editor-tested shopping awards, the Shop Smart Guide. The idea is simple: Every month, The Kit editors exhaustively test-drive items in desert-island categories — not the season’s exciting yet ephemeral trends but the evergreen essentials you’re most likely to buy now and wear or use forever. We’re talking mascara, jeans, retinol serum, black turtlenecks, white sneakers, etc. Our hope is that Shop Smart helps you reach that mythic shopping ideal: to buy less but better. Here, our guide to black sunglasses.

Let us travel back for a second to the early aughts fashion scene. Side-bangs reigned supreme, Balenciaga’s Motorcycle bag swung on every famous forearm and celebrity street style reached a fever pitch. Tiny Olsen Twins with giant Starbucks cups, Sienna Miller teetering around London in ankle boots and Kate Moss being Kate Moss—all splashed across the pages of People StyleWatch.

It was pre-social media and the only way we got a glimpse of our idols’ personal aesthetic outside the red carpet was through tabloid pics of them out in the wild. Was it a gross invasion of privacy? Absolutely. Was it also a treasure trove of actually achievable outfit inspo? You bet.

Invariably, a key component of a good celeb street-style look—even more essential than the aforementioned Moto bag—was the sunglasses. They were big, they were dark and they absolutely made the outfit. Though their primary purpose was likely to render the A-list wearer anonymous, they seemed to have the opposite effect, reminding us of just how cool the person behind the lenses was.

Black sunglasses have a way of doing that, imbuing anyone—even we non-famous folks—with alluring nonchalance. Slip on the right pair and suddenly every outing feels like a street-style moment waiting to be papped. But what exactly constitutes the “right” pair? To help you narrow down your search, I test-drove dozens of options, comparing cost vs. quality, trendiness vs. timelessness. Here is my verdict.

Ray-Ban Original Wayfarer Classic, $204, altitude-sports.com SHOP HERE

The review: Ray-Ban’s Wayfarers have been the frames of choice for many a movie star and musician. Notable wearers have included Debbie Harry, Muhammad Ali and Tom Cruise in Risky Business, among others. They are as classic as it gets, yet something about them—maybe their unique trapezoidal shape or tilted lenses—hints at a slight rebellious streak that makes them feel like the height of cool, even nearly seven decades after launching. As long-time disciple Sienna Miller (see aforementioned street style pics) recently told Vogue, “They just don’t date.” Note: These have G-15 lenses, meaning they are green in colour and only allow 15 per cent of visible light to pass through, while fully blocking UV rays. Ray-Ban also makes a polarized version at an extra cost.

Maguire Bai sunglasses, $95, maguireshoes.com SHOP HERE

Best designer look for less: Maguire

The review: Montreal shoe label Maguire expanded into sunglasses this summer and, predictably, their first pair is just as covetable as their exquisitely designed footwear. With their trendy, soft-cornered rectangular shape and thick frames, these could easily be mistaken for pricey, big-name shades, yet they retail for under $100. (Shoutout to their snazzy Kelly green case—a nice added touch.) Even better: They’re made out of recycled plastic.

BonLook Lyra Sunglasses, $199, bonlook.ca SHOP HERE

The review: In 2011, Canadian brand BonLook set out to revolutionize the way we shop for eyewear, making the process more streamlined and affordable, without scrimping on style. It’s since become famous for its sleek specs, but its sunglasses are equally deserving of praise. Take these cat-eye beauties with their sharp points and swooping lenses: impossibly glamorous and available with or without prescription lenses, including progressive, degressive and anti-fatigue.

Jenny Bird The Y2K Sunglasses, $220, jenny-bird.ca SHOP HERE

Best rectangular sunglasses: Jenny Bird

The review: Aptly named “The Y2K,” this slim rectangular frame from Canadian jewellery wonder Jenny Bird has a decided Matrix vibe. The flat profile and horizontal silhouette makes even the plainest of ensembles appear as though it was plucked from the runway, though looks are far from the only thing they have going for themselves. The frame is hand-crafted out of biodegradable acetate and the silver-plated hinges are made of recycled steel and while the tips, also plated in silver, are recycled copper. Plastic sunnies can sometimes feel flimsy, but these boast a weightiness that screams premium.

Oscar Wylee Pia Sunglasses, $169, oscarwylee.ca SHOP HERE

Best oval sunglasses: Oscar Wylee

The review: If the rectangular look isn’t your thing, this is a great way to dip our toe in the throwback pool. The oval lenses and thick temples nod to the ’90s while the high hinges impart a faint feline feel that just drips fabulousness. You know who we’d see rocking these? Meredith Blake in The Parent Trap, a sorely overlooked style icon (and vastly misunderstood villain). Bonus: The elongated curved silhouette happens to suit a slew of face shapes.

Clearly SunHarbor-51 Sunglasses, $50, clearly.ca SHOP HERE

The review: Again in the oval category, this wireframe option is a wonderful dupe for Hailey Bieber’s go-to sunnies of the summer. Hers are Balenciaga (a lot of Balenciaga in this story) and no longer available on the brand’s website, but who cares when you can snag these babies up for just 50 bucks? The black skinny frame can be paired with a bevy of lens colour options, from the more traditional black or dark green to the wilder orange or pool blue. They’re lightweight and comfortable, complete with plastic nose pads to ensure a snug fit.

Bailey Nelson Gloria Sunglasses, $145, baileynelson.com SHOP HERE

Best oversized sunglasses: Bailey Nelson

The review: In an episode of Keeping Up with the Kardashians, Kim Kardashian shared that then-husband Kanye West had sent her an email declaring, “You cannot wear big sunglasses anymore. It’s all about tiny little glasses.” Well, no offence to Mr. West, but the oversized look is back. With their elegantly sloped browline and generous, but not over-the-top frame, these sunnies from Bailey Nelson make an excellent pick. Just as perfect for fleeing the flashes as they are for early-morning drop-offs, they make you look polished and put-together even when you feel anything but.

Warby Parker Cawley Sunglasses, $150, ca.warbyparker.com SHOP HERE

Best round sunglasses: Warby Parker

The review: With its keyhole nose bridge and round lenses, this design from Warby Parker has a sort of 1940s college professor thing going of which we are very much in favour. (An ideal accessory to complement fall’s major prep-school fashion trend.) The quality is top-notch, too: They’re made from hand-polished cellulose acetate and the screws are coated in something called Akulon, a high-performance polyamide often used in the automotive and electronic sectors, for added durability. Also good to know: The lenses are scratch-resistant and block out 100 per cent of UV rays.

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