For the most part, watch collectors seem most fixated on collecting tool watches from the ’60s and ’70s. It’s not at all unwarranted — these were the glory years of innovation and design for the industry, but there’s a misconception that watches born after the wake of the Quartz Crisis in the ’70s and ’80s aren’t quite so collectible. But by the mid-to-late ’80s, watchmakers — imbued with a new focus on luxury — were once again making some seriously great watches. Given that collectors have been focusing less on watches from the ’80s, ’90s and ’00s, this provides frugal watch enthusiasts the opportunity to snatch up these watches at relatively low prices before they inevitably appreciate once everyone else catches on.
2000 Omega Speedmaster Professional Moonphase

What we like: One of Omega’s key releases last year was its Co-Axial Speeedmaster with a moonphase, but it wasn’t the first time the apropos complication graced the “Moonwatch.” Omega produced a relatively short-lived run of moonphase versions of the Speedmaster Professional from the late ’90s to the early’00s. Given that you’re getting two of our favorite mechanical complications in the shape of one of the watch world’s most iconic pieces, its $3,850 price tag feels like a total steal.
From the seller: Excellent case with light wear from use. Running at COSC spec.
1990 Rolex GMT-Master “Coke Bezel”

What we like: The GMTs of the ’80s and ’90s weren’t too dissimilar to those of today, but they do come in at a very good drop in price from brand new or earlier vintage iterations. Better still, two of the model’s best bezels — the cola-themed “Pepsi” and “Coke” color schemes — were available. This example from 1990 has the latter, which gives an otherwise reserved watch a subtle pop of color.
From the seller: Comes with a lightly faded and scratched-up Coke bezel insert. Running at COSC spec.