The Most Stylish Men’s Watches of 2023

It’s Hip to Be Square

Though the watch world can be intimidating, it’s more similar to the rest of the menswear industry than you might think. What looked great decades ago (like the Oxford shirt or the navy blazer) has true staying power. Such is the case with square or rectangular watches. 

Timepieces weren’t always so large and blinged-out. In fact, stylish folks kept time with pocket watches before companies streamlined the process. Watches were also naturally smaller in terms of case diameter and shape: The Cartier Tank Watch debuted in 1917 in an homage to the French Renault FT-17 Tank, yet has maintained an elegant and undersized look across the years. 

It’s a watch that invites a closer look; real ones know that tank watches stand out by nature more than a classic round face. Companies like Fossil make affordable versions these days, and the Versace Dominus has sporty, luxe appeal with a triple chronograph design for a change of pace. When everyone else is wearing a timepiece with a standard circular face, opt for a dressier, crisp square or rectangular case design. 

Cartier Tank Must Watch

Fossil Carraway Three-Hand Brown Leather Watch

Versace Dominus Watch

All That Glitters Is… Bronze? 

Watchmakers have tried to gain an edge in the market for years, leaning on durable materials like stainless steel and coatings like black carbon for points of differentiation. And there’s a plethora of strap options, from dressy leather varieties to sporty rubber strap watches on timepieces made for diving. 

Sleek, classic stainless steel in silver is a go-to move for many dive watches, which feature thicker links and water-ready capabilities made to go diving deep depths. These watches also tend to work well for rugged adventurers (James Bond even wears a stainless steel diver with a tuxedo—debate amongst yourselves if that’s the correct move). But the real style swerve? Outfitting that stainless steel case with a bronze finish, or a bronze bezel (as Huckberry did in a recent collab with dive watch masters Zodiac).

The watch will develop a handsome patina over time, just like your favorite selvedge jeans or brown leather boots. And unlike some other stainless steel or titanium dive watches, a bronze watch often clocks in at a (slightly) lower price point while still serving as a highly distinctive “entry-level,” rugged-meets refined timepiece. 

Huckberry x Zodiac Bronze Super Sea Wolf Dive Watch

Shinola Bronze Monster Automatic Watch

A Time-Tested Investment (in Rolex) 

Hold onto your hats: If you’re just revving up your engine in the world of watch shopping, a vintage watch might not be the most advisable move. Unless, of course, you’ve had your eye on a sort of “holy grail” watch for years. Either way, it’s astonishing how a watch can climb in value, utility, authenticity, and appeal over the years.

Rolex watches have proven a more valuable investment than real estate over the last decade. Is it worth sinking all you’ve got into a timepiece? Again, tread with caution, but Rolex watches are a heavyweight for a reason. They’ve got serious juice in terms of iconic style and performance, and greats like Paul Newman trusted Rolex for a reason. 

He’s but one in a long list of greats who wore the famed brand, but there’s something undeniably cool about a vintage watch with heritage. Experts certainly agree: Paul Altieri, CEO of Bob’s Watches, said that the Rolex Ref. 6241 Daytona “Paul Newman” with white dial has exceptional pedigree. 

The timepiece is named so because Newman wore a similar Rolex Daytona with an “exotic” dial and a red outer seconds track, so it’s a look worth emulating in that regard. “This is one of my favorite watches and vintage Rolex models overall,” Altieri tells StyleCaster. “This year I found myself gravitating towards it more and really enjoy wearing it.”

There are watch forums and books dedicated to the vast Rolex universe (and there are more than enough Rolex watches to lust over). And hey, I never said they were affordable, but if you’re ready to take the leap, climb in and start your engine. 

Rolex Submariner Black Dial Stainless Steel Watch

Rolex Air King Oyster Perpetual Watch

Vintage Rolex Daytona 6241 Paul Newman Watch

The Triumph of Timex

If you’re anything like this writer, Timex was perhaps one of the first watch brands you wore, or bought with your own money, or both. They make simple, uncomplicated watches that quite literally take a lickin’ and keep on tickin’ (as the old advertisements go), but the buck often stopped there—until about six or seven years ago. Under the guidance of Milan-based design director Giorgio Galli, the iconic American watch brand both leaned into its historical archive while freshening up its arsenal of designs for the present day. 

Chief among these leaps was a partnership with famed American menswear designer Todd Snyder. Timex gave the Iowa-born Snyder, a longtime fan and wearer of the brand, access to its archives to work on co-branded, retro-minded timepieces that retailed for incredibly low prices, looked seriously cool, and sold quickly. 

That partnership shows no signs of slowing down, and the brand has only gotten better. Timex made a series of watches in America (the American Documents Collection) and mined a golden age for watches, the 1970s (the result is the ongoing Q Timex Reissue series). Is Timex cool? You could say they never stopped, but these days, if you wear a sharp Timex watch, you’ll get (positive) questions and second glances. 

Timex x Todd Snyder Watches

Q Timex Stainless Steel Reissue Watch