The immediate disclaimer on this post is that I don’t own these watches. I admire them. I would like them. And one day, I might. But for now, I’m content in appreciating their design, status and allure.

Here’s my belief on watches: A gentleman should own a classic timepiece. And he should invest in a watch that will last. This watch should be passed on to his child. It’s an investment in quality and legacy.

With that belief in mind, here’s what has caught my eye over the years. In no particular order.

TAG Heuer Monaco

Steve McQueen wearing the TAG Heuer Monaco watch

From Wikipedia: The TAG Heuer Monaco (originally Heuer Monaco) is a series of automatic chronograph wristwatch originally introduced by Heuer in 1969 in honour of the Monaco Grand Prix. The Monaco was revolutionary for being the first automatic as well as the first square cased chronograph. The Hollywood film star Steve McQueen used the watch to accessorize his character in the 1971 film Le Mans. In the decades after his death the use of film stills has made the watch synonymous with McQueen. Although it was discontinued in the mid-1970s, the Monaco was reissued with a new design in 1998 and was reintroduced again with an entirely new mechanisms in 2003 in response to McQueen’s increasing popularity.

So – a beautiful design, and a tip of the hat to Steve McQueen, and inspired by the Monaco Grand Prix? Yes please.

Prices range – $2,500 and up.

Breitling Chronoliner

Breitling Chronoliner

From the Breitling site: Inspired by a Breitling model from the 1950s and 1960s, the Chronoliner asserts itself as an authentic captain’s watch. Its broad black bezel in scratch-resistant high-tech ceramic, featuring an original star-shaped cut-out, enables simple reading of the second timezone in 24-hour mode. Just the ticket for a long-haul flight anywhere in the world. The performances of the chronograph are displayed on counters placed at 12, 9 and 6 o’clock. The black dial is distinguished by a degree of legibility worthy of the finest flight instruments.

I often wish I was a pilot in the 1960’s that required a watch to successfully fly a plane. I feel like that would have been a good life for me. And the watch is pretty damn cool looking.

Price range – around $6k.


Rolex GMT Master II Red Blue

From the Rolex site:

GMT-Master II g • m • t • mas • ter • two

  1. A legend of the jet age, the original GMT-Master was embraced by airline pilots as their on-board navigation chronometer.
  2. An iconic two-time-zone watch with an arrow-tipped 24-hour hand and a graduated rotatable bezel.
  3. The first Rolex to feature a Cerachrom bezel, impervious to scratches and harder than steel.
  4. The perfect way to navigate a connected world in style.
  5. The Rolex Way.

Hmmm. A Rolex. With the famous Pepsi bezel?  Where do a sign. Or maybe not…

Price range – $41,000.



Another watch inspired by motor racing. I’m in love with its elegance. ’nuff said.

Price range –  You’re looking at the $3,000 range.

Omega Speedmaster

Omega Speedmaster Professional

We’re talking about the first watch to be worn on the moon. For a space and science fiction geek like me, that’s pretty cool. It’s also known as the ‘moon watch‘: The OMEGA Speedmaster is one of OMEGA’s most iconic timepieces. Having been a part of all six lunar missions, the legendary Speedmaster is an impressive representation of the brand’s adventurous pioneering spirit.

Price range – $3-4k.

Also, I’ve got lots of other watches on a very specific Pinterest board. Isn’t that what all middle-aged men do?

Thanks for reading! These watches are pretty cool, huh?