In our price-bracketed buying guide, we examined great vintage and pre-owned watches under $15,000. This time, we’re upping the ante a bit into heirloom territory. Here, you’ll find double-signed pieces from famous retailers; rare tool watches from the golden age of recreational SCUBA diving; contemporary collaborations with notable architects and artists; and much more. Spanning dress watches, tool watches, and everything in between, these timepieces are certainly not impulse buys — but once you consider their unique feature sets, handsome aesthetics, and rarity, there’s no doubt that you’ll find them as compelling as we do.
Patek Philippe Calatrava 'Backwind' ($15,990)
Patek Philippe Calatrava 'Backwind' - IN THE SHOP
In production since the 1930s, the Patek Philippe Calatrava is the golden standard of dress watches. But in the 1970s, the collection got a bit — well — funky! Check out this incredible ‘Backwind’ reference, for example: Housed in a white gold case with an integrated bracelet, it features an eye-catching, blue guilloché ‘Sigma’ dial and winds via the caseback.
Bulgari Octo Finissimo Sejima ($16,250)
Bulgari Octo Finissimo Sejima - IN THE SHOP
Produced in concert with Pritzker Prize-winning Japanese architect Kazuyo Seujima, this special version of the highly lauded Bulgari Octo Finissimo automatic is powered by an in-house micro-rotor calibre that yields a case just 6.4mm tall. Of course, the star of the show is the watch’s dial: consisting of hundreds of metallized dots, it’s unlike anything else on the market.
Breitling Superocean 'Slow Counting' Chronograph ($16,500)
Breitling Superocean 'Slow Counting' Chronograph - IN THE SHOP
We’ll bet you’ve never seen a diver’s chronograph quite like this before! The Breitling Superocean Reference 2005 features a central-minutes counter: When activated, it makes its way slowly around the periphery of the dial, while a cutout above 6 o’clock turns white to let you know that it’s actuated. Clever and useful, it’s housed in an oversized, 42mm steel case.
Universal Genève Compax 'Evil Nina' Mk I ($17,850)
Universal Genève Compax 'Evil Nina' Mk I - IN THE SHOP
This reverse-panda version of the ‘Nina Rindt’ Compax is a compelling racing chronograph with a winning feature set: Its Valjoux 72-powered, triple-register chronograph is plenty useful in timing races — or anything else! — while its unique handset, handsome black dial, twisted-lug case, and included burgundy leather rallye strap are sure to turn heads at the track.
Jaeger-LeCoultre Master Ultra Thin Perpetual Calendar Moonphase ($18,500)
Jaeger-LeCoultre Master Ultra Thin Perpetual Calendar Moonphase - IN THE SHOP
If you have another source for an ultra-thin perpetual calendar powered by an in-house movement — with a beautiful dial, to boot — for under $20K, we’re all ears! The Reference Q1308470 measures a perfect 39mm in stainless steel and features day, date, month, moon phase, and year displays. Handsome and well proportioned, it’s perfect for everyday wear.
Heuer Autavia GMT ($18,900)
Heuer Autavia GMT - IN THE SHOP
This Ref. 2446C is so packed with useful features — and so darn colorful — that it’ll take an act of tremendous willpower to keep any sane watch lover away from it! Housed in a 40.5mm stainless steel case, it features a GMT complication, plus a triple-register chronograph, plus a gorgeous dial, plus a Pepsi bezel, plus a super-cool ‘beads of rice bracelet.’
Breguet Tradition Yellow Gold ($19,500)
Breguet Tradition Yellow Gold - IN THE SHOP
This 37mm number from Breguet is mesmerizing in every sense: Bridging the maison’s 19th century aesthetics with modern technology, it pairs a beautiful, hand-wound movement with a visible, straight-line lever escapement to a subsidiary, guilloché dial and a power reserve indicator. Executed in yellow gold, it’s a powerful reminder of Breguet’s top-notch workmanship.
Cartier Délices White Gold ($21,900)
Cartier Délices White Gold - IN THE SHOP
A far cry from the ‘iced-out’ pieces seen courtside and at fashion shows around the world, this subtle Cartier Délices makes subtle use of diamonds around its ovular bezel to convey a sense of class and dressiness. Its silver guilloché dial with Roman numerals, meanwhile, reminds us that this is a Cartier, while its thin, white gold bracelet recalls vintage cocktail watches.
Cartier Tank Americaine Platinum ($22,500)
Cartier Tank Americaine Platinum - IN THE SHOP
A modern take on the famed Cintrée, the Tank Americaine was initially launched with quartz movements — but this platinum-cased version from the 2000s features a manually-wound movement. With its handsome silver ‘Roman’ dial, sapphire cabochon winding crown, and blued steel ‘sword’ handset, it’s everything we love in a classic Cartier configuration.
Patek Philippe Calatrava 'Gübelin' ($23,000)
Patek Philippe Calatrava 'Gübelin' - IN THE SHOP
There’s nothing quite like a simple, solid-gold dress watch — but this fabulous Calatrava isn’t so simple. With its 36mm Wenger case, stepped bezel, screw-down caseback, and automatic movement, it’s perfectly proportioned — but the silver dial, double-signed by Gübelin and featuring handsome ‘dart indices — truly sends it over the edge.
