The Rolex Datejust is one of our all time favorite dress watches.  It’s still considered a daily wear watch in some respect, but not so much as a Daytona or Submariner.  Datejusts encompass everything the Rolex brand stands for- quality, style, and eloquence.

So what CAN you pair the Datejust with? Is it dressy enough for a cocktail party? Should you wear one on your next business trip? During a workout? We’ve read all the men’s fashion blogs and combed through endless style feeds so you don’t have to.  And here at Jonathan’s we just know a thing or two about fashion.

Let’s have a look at our favorite ways ways to style a Rolex Datejust:



Some may consider pairing a Datejust with a tuxedo a stretch, but we call it coloring outside the lines.  Rolex actually features the Datejust 31 and 36 models in its ‘Black Tie’ campaign.  If you follow ALL the rules, you’ll miss all the fun.

For those that like a more traditional black tie watch- ensure you’re choosing a Datejust with the following features:

  • a simple and elegant dial- black works perfectly here
  • more formal Roman numerals or markers versus numbers
  • a bracelet and case to match cufflink hardware
  • a black leather strap

Keep in mind it’s bad form to check your watch at a formal affair, but if you must- don’t be conspicuous.



Now THIS is a look we can all agree on.  The Datejust looks great with just about any suit- whether you’re attending a wedding, business conference, or a holiday cocktail party.

Typically in those types of settings, you don’t want all the attention.  Maybe a little- but wearing too loud or eccentric of a watch, like a Sky-Dweller can send the wrong message. (Unless you’re a pilot, then by all means!)

Pairing a suit with the Datejust makes just the right statement.  Clean, classy, professional and confident (but not TOO confident).  You can also get away with a bit more color and combination with the dial and bracelet here.

See also: The Datejust II vs. the Datejust 41



As we mentioned before, many consider the Rolex Datejust a daily wear watch, mainly due to the cyclops lens over the date complication.  If your daily attire features a traditional button down, collared shirt with slacks, the Datejust is perfect.  Maybe you’re an investment banker or real estate mogul and your daily wear is slightly more elevated.  (If so, see above).

For some industries (like start-ups and tech) today’s business casual has expanded broader than the sports coat and slacks look.  It’s more dressed down and relaxed than ever- sometimes referred to as ‘smart casual’ or just ‘casual.’  That might look like a sweater or polo with jeans, or a sport coat and sneaks.

The good news is the Rolex Datejust is extra versatile.  You can float straight from an office meeting into happy hour.

Related: Rolex Datejust 116300



What???? Nahhhhh. Hear us out. The Rolex Datejust is definitely dressier than it’s daily wear Submariner counterpart, but we’ve still seen some guys pull it off with a t-shirt.   Zac Efron case in point.  And it’s a pretty bad ass look.

If you’re going to dress it down, make sure it’s with a neutral but bold color like black.

It’s super common to see celebs pairing their Rolexes with street wear and extra casual looks.  They have the power and prestige to get away with any style they want.  So why can’t we?!

Whether it’s a more formal, traditional look or a dressed down version- the Datejust can pull it all together.  At the end of the day, it’s your watch and you can only pull off what you’re confident enough to try.


If you are interested in purchasing your own Rolex Datejust, give us a call or fill out our contact form. Check out our Facebook page for box openings and watch reviews by our in-house watch expert Sergio Nuncio!

Sergio Nuncio

Jay Freedman

Keifer Nuncio








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