I get this question frequently.  Many people want to own their first Rolex and they are not sure where to begin.  The obvious first question is whether you have specific functional needs offered by the various Rolex models.  If you love racing the Rolex Daytona is a perfect fit.  Pilots would be ideally suited for the Sky-Dweller.  Divers would likely opt for the Submariner or DeepSea.  Yachtsman would likely lean toward the Yachtmaster or Yachtmaster II models.  Climbers would best be suited by the Explorer model.  Are you around high magnetic fields or are you a scientist at heart?  Then the Milgauss would fit your needs perfectly.

But let's assume you don't partake in any of these hobbies and want to pick a timepiece that fits your tastes.  Should you just opt for a DateJust and call it a day?  Not necessarily.  Although the Datejust is a perfect first Rolex for many people, it may not be the perfect first timepiece for you.

Yellow Gold Presidential Rolex Day-Date

One question I like to ask is "How you intend to use the watch?"  If you travel frequently, a GMT Master II is a great timepiece that allows you to keep track of 2 time zones.  If you are an executive a Yellow Gold Presidential Day Date would definitely make a statement that you are the top of your game and mean business.  And since it is a favorite of Jack Nicklaus, you know it would be a winner both in the boardroom and on the links.  I personally like the Day Date because of the Day of the Week function at the top of the timepiece - a feature that isn't on any other Rolex and something I chronically need.  However, a simple Cellini Moonphase would be the classic timepiece that would fit your suit and tie without breaking the bank and since it is battery powered, you can swap with multiple timepieces without worrying about keeping it wound. 

Rolex Datejust

If you just want a solid masculine looking Rolex timepiece that could function well both at work and at play without being overly ostentatious, I would say a stainless steel Datejust, a Submariner with Date, Explorer II, or a GMT Master II with a black bezel would be a perfect cross over timepiece.  Take your pick there.  They would all be perfect first Rolex timepieces, and many of them won't break the bank.

Another question you might ask is "How big is the Rolex?"  You will find men's Rolex sizes ranging from 36 mm to 44 mm.  So, depending on the size of your wrist, you may opt for a larger or smaller size. 

Rolex Yacht-Master II

Have a favorite color pattern?  If Blue is your thing, the Yacht-Master II has a beautiful look for you.  Yes, you can find a Datejust with a blue dial, or a GMT with a Red and Blue "Pepsi" bezel.  However, the Yacht-Master is a classic timepiece with the Red White and especially Blue to proudly wear. Check out the new Milgauss with Blue-Green coloring as well. 

Rolex Pearlmaster

Ladies have the luxury of choosing smaller size timepieces as small as 28 mm and diamond or sapphire encrusted bezels such as the Pearlmaster series, or having their wide choice of the men's Rolex collection.  It is more than fine for a woman to sport a Rolex Daytona, making Danica Patrick proud. In fact, my niece has been sporting a Rolex Daytona of her own for the last couple years and loves it.