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The 10 Best Luxury Watches for $5,000 Or Less

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Continuing our extremely popular survey of the best luxury watches at various price points, we hereby present the $5,000 and under category (check out our Best Under $4,500, Best Under $3,500 and Best Under $2,500 roundups). 

As always our advice is figure out the most you can possibly afford to spend on a watch which will become a future heirloom, then zoom in on the want you want with the help of our handy guide:

Rolex Datejust Turn-O-Graph, $4,400

The Turn-O-Graph, very covetable but a bit of an oddity in the Rolex catalog, was the brand's fist pilot watch and the first to feature a rotating bezel. 

TAG Heuer Monza 40th Anniversary Edition, $4,400

In 2016 when TAG re-issued one of the coolest watches in the Heuer archive the price was a bit high, but you can score this one for over $1,000 less.

Cartier Roadster Chronograph, $4,500

We have always loved this sporty take on Cartier's classic tank watch, and as it is no longer produced we think it has major appreciation potential.

Bremont U-2 Limited Edition, $4,500

Badass British brand Bremont designed this limited edition beauty in homage to the U-2 spy plane, flown by the CIA and then the U.S. Navy since 1955.

Jaeger-LeCoultre Reverso Grande Taille, $4,600

Reversos, originally designed for polo players so their watches could be protected in play, is an all-time icon and this two-tone version is fairly rare.

Panerai Luminor Automatic Titanium, $4,797

Titanium, tougher and lighter than steel, is a major upgrade over a base Luminor that in this case won't do much damage to your bottom line.

Tudor Black Bay 58, $4,800

Paying tribute to Tudor's very first dive watches, this retro-styled stunner clocks in at a smaller, era-appropriate 39mm size that's more subtle than most.

IWC Portuguese, $4,800

A real deal in steel as opposed to gold, IWC's most handsome chronograph is sporty elegance personified and is sure to turn plenty of heads.

Omega Speedmaster 50th Anniversary Moonwatch, $5,000

This rare Speedmaster is known as the "Patch" thanks to the Omega seahorse logo on the dial at 12 o'clock, denoting a 50th-anniversary model. 

Rolex Oyster Perpetual, $5,150

The blue dial on this iconic 39mm beauty lends it a dashing, somewhat nautical air, with a size that won't speak any louder than you want it to.