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100 Percent Glendale ($185)

The sunglasses cosmos is vast and full of wonder. Consider this racing shield, which warps taste and creates a convergence of ugly-old and beautiful-new. The laws of lookin’ good no longer apply. The Glendale takes us back to the mid-1980s, when an obscure company called Oakley put weird optical gear on America’s first national-hero bike racer, Greg LeMond. The California brand’s epochal Eyeshade looked a lot like someone had hinged sunglasses temples onto a pair of motorcycle goggles. Now, 35 years on, history repeats itself. 100 Percent (like Oakley, a company respected in motocross circles) gifts cyclists and runners a rootsy shield with premium 21st-century materials. Two lenses are included—smoke gray and nearly clear, both of which work well from noon to night—and the Glendale’s heptagonal frames flex for easier swapping. There’s no missing those frames, especially in mustard yellow with a titch of black striping. Unless you happen to be wearing them, in which case there isn’t much to see but a world blazing past while you’re sheltered from harsh sun and wind. Just enough defogging air wafts in through perforated front vents and out the scoops at the temples. No amount of huffing or sweat clouded the lenses. We couldn’t help but love every part of the Glendale, and that earned it Gear of the Year.

Smith Lowdown Steel ($199)

Best for Every Day

Smith delivers easy, all-around likability with these shades, which are amenable to streetwear and light outdoorsiness. In town or the boonies, the brownish tint of the polarized synthetic lenses make the world look bright and colorful. This is the bazillionth redo of the classic dorky-cool Wayfarer from the 1950s, but Smith adds an original touch in the form of a metal section—noticeable but not flashy—at the temples. Though the Lowdown Steel is up for casual rec like jogging or city biking, the look is a bit dressy for sport. The shape works well on anyone, provided you don’t have a huge head.

Rapha City Round ($215)

Best Behind the Wheel

A moment of color adjustment is a small price to pay for what the City Round’s brown-tinted synthetic lenses do for visual acuity and comfort. The view is delicious, even driving down the mountain and straight into low but hellishly bright sun. The peripheral view is open to wind and light, so these shades aren’t ideal for serious activities, but they rock in unnatural settings. They’re ideal for car duty and a good fit for urbanites looking to avoid tired, formulaic hipness. The temples are made of slender dark steel—an artful industrial clash to vintage-looking tortoise frames—and lock open or shut.

Kaenon Anacapa ($209)

Best for Extreme Pursuits

This expedition-grade sport wrap is named for a SoCal Channel Island beaten to pieces by the Pacific. Meanwhile, the dark gray, mirrored, polarized synthetic lenses belong to a new line called Summit. Marketing names are usually beside the point, but here there’s real intent, since oceans and mountaintops are tough on the eyes in similarly windy, searingly bright ways. The Anacapa provides a little bit of heaven when conditions are harsh. The wrap-back lenses and abundant sculpted frames provided security and protection on a hike up a sun-bludgeoned peak amid high-wind warnings.

Roka Torino ($170)

Best Training Shades

Hand it to Roka for knowing how to make sunglasses aimed at go-fast jocks that are truly stylish and—better yet—fun. In this case, the fun is a throwback design with squarish oversize synthetic lenses. Very 1970s. Don’t let the mirroring and two-tone blue and orange trim blind you to the Torino’s sporty bona fides, especially for running and cycling. Coverage and protection are big, like the lenses, with super-sharp optics in a neutral gray tint that also works in town. Springy featherweight frames hold on to your head and have sticky-when-wet rubber patches. Sweat and look cool.

Rudy Project Spinair 56 ($200)

Best for Almost Everything

You’d never guess there’s a grown-up in the room by the look of these lenses, mirrored red like the flames of hell, plus faux-carbon-fiber frame patterning and the shrieking crimson R-U-D-Y and rubber cladding at the ears. Rudy’s polarized lenses are about as optically superb as synthetic gets. The gray tint means even modest adventurers will love wearing the Spinair. Kudos to the brand for setting top-end polarized lenses in so intense a colorway. Beneath the surface, the Spinair 56 is solid crossover eyewear for playing and kicking back when the sun is serious but you’re not.