As a wayward journalist in New York, I have a soft spot for the film Bright Lights, Big City—a neon-lit fever dream starring Michael J. Fox as Jamie Conway, a debauched yet oddly endearing writer. As Conway stumbles through nightclubs, office corridors, and women’s bedrooms across Manhattan, he sports distinctive sartorial armor: a tweed blazer, crisp khakis, and always, a pair of Ray-Ban Wayfarers—worn even indoors to mask his bloodshot, cocaine-blown eyes. He may not be the most upstanding guy, but his charisma is undeniable—sleazy charm accentuated by ever-present, classic shades.
Sunglass trends come and go. Back in my college days, BluBlockers were all the rage one summer, after Zach Galifianakis’ character wore them in The Hangover. As an adult, I wouldn’t be caught dead wearing those ugly bastards. But some styles are eternal. Ray-Ban Wayfarers and Persol 714s were cool in the ’60s, cooler in the ’80s, and are still cool today.
Below are six sunglasses with timeless swagger—classic shades that will never go out of style.
American Optical Saratoga
Founded in 1833, American Optical is the oldest eyewear company in the United States. The brand’s Saratoga sunglasses became iconic after John F. Kennedy was frequently photographed wearing them—from sailboats to lavish parties to podiums before starstruck crowds. The lenses feature a subtle green tint, while the vivid tortoiseshell pattern embellishes the acetate frames. True to its roots, AO still proudly manufactures every pair at its factory just outside Chicago.
Ray-Ban Wayfarers
The signature shades of Bob Dylan and James Dean, Ray-Ban Wayfarers have been the eyewear of choice for fashionable rogues and dapper rolling stones since 1952. Designed by optical visionary Raymond Stegeman, the sleek, angular frames drew inspiration from mid-century modern architecture and the tailfins of American muscle cars. Universally flattering, they pair as effortlessly with raw denim as they do with a bespoke suit. Decades after their debut, Wayfarers still manage to look enchantingly cutting-edge.
Photo via Randolph USA
Randolph P3
Proudly crafted in Massachusetts, Randolph sunglasses are as quintessentially New England as shotgunning a Sam Adams at a clambake on the Cape. Originally designed for military and commercial pilots, Randolph’s frames—especially their Aviators—are built to withstand the cockpit’s harsh glare. The P3s offer a rounder take on the classic aviator silhouette, with satin gold frames, polarized lenses, and Randolph’s nonpareil craftsmanship. The P3’s circular lenses bring to mind the shades favored by John Lennon.
Photo via Persol
Persol 714
Founded in 1917 by Turin-based designer Giuseppe Ratti, Persol takes its name from the Italian phrase “per il sole,” meaning “for the sun.” The brand’s signature silver arrow, inlaid on the acetate arms as a nod to ancient warriors, makes every pair instantly recognizable. The Persol 714 became iconic thanks to Steve McQueen, the 1970s sex symbol dubbed “The King of Cool.” He famously wore them in The Thomas Crown Affair and sported them off-screen while carousing through Hollywood. McQueen favored the tortoiseshell frames with light blue lenses, but I prefer the brown lenses—they’re more versatile and pair easily with a wider range of outfits. Engineered with six joints, the Persol 714s fold down into a compact, disc-like shape for easy storage.
Photo via FramesDirect
Brooks Brothers BB5050U
You can trust a brand’s old-money cachet when its logo is drawn from ancient Greek mythology. Brooks Brothers’ insignia, a golden sheep suspended from a ribbon, honors both the Golden Fleece of the Argonautica and the traditions of modern wool merchants. The tortoiseshell frames, made of high-quality acetate, complement the olive green lenses. Long synonymous with preppy luxury, Brooks Brothers’ shades pair best with a seersucker blazer, linen trousers, and martinis and cigars on a porch in Edgartown.
Photo via Barton Perreira
Barton Perreira Armstrong
Bill Barton and Patty Perreira, both veterans of Oliver Peoples, founded Barton Perreira with the mission to eschew fleeting fashion trends in favor of timeless design. Based in Los Angeles, the brand has become a staple among Hollywood and Malibu’s glitterati. If Jackie Treehorn, the wealthy rake from The Big Lebowski, were a real person, he would probably rock a pair of Barton Perreiras with his smoking jacket. While the aesthetic is unmistakably SoCal, the craftsmanship is Japanese, with each frame meticulously produced in Fukui Prefecture. The Armstrong, made from ultra-lightweight titanium, comes in both sunglasses and reading glasses.
