The Best Picks for Your First Luxury Watch, From Rolex to Omega

Building up your watch collection is an expensive endeavor, and it helps to know where to start.

From the timeless Rolex to a six-figure Richard Mille, exclusive watches are often spotted on the wrists of billionaires — and if you know the model, you know. It can seem intimidating to step into that world. And if you have the cash and the patience, you can enter their ranks.

But first, you’ve got to do your homework. Craftsmanship, brand history, and resale value are important factors to consider before committing to a purchase. Paul Altieri, founder and CEO of watch reseller Bob’s Watches, advises potential buyers to take their time and get involved with the watch community by attending events and joining online groups or local clubs,

People should “research models known for their investment potential, such as certain limited editions or pieces from prestigious brands,” Altieri said.

Of course, you could look to Oracle CTO Larry Ellison and collect Richard Mille pieces, or wear the same model of Omega watch that Amazon founder Jeff Bezos wore to space.

But “remember, collecting luxury watches is a personal journey,” Altieri said.

These are Altieri’s top starter watch picks from the luxury brands beloved by the wealthy. All prices cited are from official sites or certified retailers unless stated otherwise.

Rolex

Men’s: Rolex Oyster Perpetual 41-millimeter diameter — $6,500 retail price

“Clean, timeless, and versatile, the OP 41 is a gateway into the Rolex world. It carries Rolex DNA without complications, which is perfect for first-time buyers.”

Women’s: Rolex Datejust 31-millimeter diameter — $7,100 retail price

“Classic, elegant, and endlessly customizable, the Datejust 31 is one of the most iconic women’s watches ever made.”

Cartier

Men’s: Cartier Santos de Cartier Medium — $7,050 retail price

“The Santos is a historic design that wears well with both casual and formal looks. It’s one of Cartier’s most iconic and versatile models.”

Women’s: Cartier Tank Must — $3,300 retail price

“The Tank Must is instantly recognizable, slim, and effortlessly elegant — perfect for a first luxury watch.”

Omega

Men’s: OMEGA Speedmaster Professional Moonwatch — $6,600 retail price

“Legendary for its NASA history, the Moonwatch is an icon that belongs in every collector’s lineup.”

Women’s: OMEGA Constellation 29-millimeter diameter — $7,500

“With its integrated bracelet and elegant design, the Constellation blends everyday wearability with a touch of glamour.”

Audemars Piguet

Men’s: Royal Oak Selfwinding 41-millimeter diameter (Ref. 15510) — $28,600 retail price

“It’s hard to top the Royal Oak as a first AP. The design is legendary, and it has a strong presence without being flashy.”

Women’s: Royal Oak Selfwinding 34-millimeter diameter — $26,100 retail price

“A more refined take on the Royal Oak, but with the same iconic design and mechanical pedigree.”

Patek Philippe

Men’s: Calatrava (Reference number 6119) — $33,113 retail price

“It’s the purest expression of Patek’s dress watch tradition. Understated yet beautifully finished, the Calatrava is how many serious collectors start their Patek journey.”

Women’s: Twenty~4 Automatic (Reference number 7300) — $29,813 retail price

“A refined, everyday luxury watch for women, with a modern automatic movement and timeless style.”

Richard Mille

Men’s: RM 005 (discontinued) — $80,000 to over $100,000 at resale

“For those entering the Richard Mille world, the RM 005 is relatively more approachable and introduces the brand’s signature case shape and technical innovation.”

Women’s: RM 07-01 — over $120,000 retail price

“A fusion of avant-garde materials and a skeletonized dial, the RM 07-01 is bold, modern, and distinctly Richard Mille.”