A Guide To Buying Your First Rolex

Buying your first Rolex watch is a big step – here are some things to think about

I am not a watch expert. The world of fine timepieces is something I am just starting to dip my toes into. And I’m doing so with humility and a reverence for those who truly are bona fide authorities, connoisseurs and aficionados.

Why? Because serious watch culture can be a seriously intimidating place. If you’re frightened by the menswear world, you’ll get a whole other world of vibes from watch geeks online – a tribe that ranges from rich dudes who smoke $500 cigars and have Wheels Up memberships to aging hipsters who have an encyclopedic knowledge of Patek Philippe and Rolex reference numbers and want you to know that they do.

It reminds me of when I was a bike racer and I would go into a bike shop for the first time where nobody knew me. The macho posturing and sizing up was not so different than what you’d see in an episode of “Wild Kingdom.” You had to check your ego at the door and let your legs do the talking.

In other words, it’s a club – an exclusive club – that grants membership through demonstrated knowledge, understanding and appreciation.

I’ve been thinking about posting about this topic for a while now because I actually purchased my first Rolex not too long ago. And while I certainly didn’t become an all-knowing expert in the process, I did a lot of thinking about what it means to buy your first Rolex, a lot of research, a lot of reflecting and a lot of back and forth on what my first Rolex would be.

first rolex watch to buy

(To all of those points, I’m a perfectionist, a crazy person when it comes to learning all I can about something I’ve deemed worthy of my time and energy and a Libra.)

As a result, I feel as though I’ve picked up a decent amount knowledge and experience when it comes to taking the plunge to make that investment.

And since I’ll wager that anyone reading this post is in the same boat as I was before buying the watch – a non- (or budding) watch geek, normal guy who wants to make the best and most prudent choice for himself – you can rest assured that wherever you are in that journey, you’re not going to be judged.

I’m here to help.

Here are some questions to ask yourself, things to think about and decisions to make when buying your first Rolex watch.

I tried to think of the entire process I went through – which took about five months, by the way – to guide you through it in a logical way. Also included: my advice, obviously. Enjoy.

first rolex watch to buy

Why buy a Rolex watch?

You should buy your first Rolex to:

1. Celebrate a milestone, achievement or success in business or life;

2. Own a timepiece that will hold its value over time – it’s an investment;

3. Wear something of quality with a storied history,

When should you buy your first Rolex?

As mentioned, buying your first Rolex is usually a mark of some type of achievement. You’ve got to be ready for it – both financially and emotionally.

First Steps: The Research Phase

Never, ever, rush into purchasing your first Rolex.

Soak up all the information you possibly can. Read and reread and reread articles from respected online publications like Hodinkee, A Blog to Watch and Time & Tide.

There are also a number of excellent Rolex forums out there. Check them out as well for a host of opinions. You probably won’t get a definitive answer from forums like these, but it is helpful to read the range of opinions from the many passionate Rolex disciples online.

At the very least, you will find at least one well-spoken contributor who will help you be more confident regardless of which way you’re leaning.

(An important note for younger HSS readers: Beware of start-up “influencers” who pretend – often in vain – to be knowledgable but hawk whatever cheap piece of Chinese crap they’re given in the guise of an “expert” review.)

New v. Vintage?

There are lots of opinions on whether to buy a new or vintage Rolex. Personally, I think a first Rolex watch should be new. Here’s why.

First, you know exactly what you’re getting. It’s brand new and has no problems (you never know the story of a vintage watch no matter how detailed the history).

Second, I think it’s nice for a first Rolex to truly be yours. As enticing as a vintage Rolex might be, it has had another owner. Wouldn’t you want to feel as though the first Rolex you buy belongs to you and has only belonged to you?

What model should you buy?

This is completely a matter of personal preference and personal style.

Ask yourself these three questions:

1. Do you want something sporty or dressy? Or perhaps something with the most versatility?

2. Do you plan to wear it every day or just on special occasions?

3. What do you want the watch to communicate about you?

Ultimately, your answers will lead you back to your underlying sense of style. Are you a classic guy? A sporty guy? A flashy guy? This will allow you to choose the best model for you.

In general, your first Rolex should be classic and timeless – a piece that you’re going to be proud to wear in 30 years.

In other words, do not buy a Rolex as a fashion statement. For your first Rolex, stay away from colored dials, oversized cases, the latest updates to classic models (the new 116710 BLNR, notwithstanding, since it’s universally regarded as a new classic) and anything that points to general flashiness.

It’s also extremely important to try a few different models on. Nothing beats this, as a matter of fact. What looks good on you? What feels right? You won’t know unless you have one on your wrist.

Having said that, here are a few options to consider.

Classic & Dressy

Oyster Perpetual. Simple, understated, classic, no-nonsense. Choose a size and a dial color.

Datejust. Perhaps one of the most classic and recognizable Rolex watches. (I realize that statement could be applied to a few models in the line, but it’s how I feel about the Datejust.) With an Oyster bracelet, it’s a bit more casual and with a Jubilee, it’s dressier.


Submariner. I don’t think there is as ubiquitous a sporty Rolex than the Submariner. There’s a reason for that. It’s a classic that will always look good. A solid choice, though be sure to consider how many others are floating around on wrists out there.

GMT Master II. For me, the GMT Master II is the thinking man’s sporty Rolex. If you want a sporty option, I think a GMT Master II is the best choice you can make. And now with the BLNR – first of it’s kind blue/black bezel in Rolex’s patented Cerachrom ceramic – it really is a true investment piece.


Explorer. Similar to the Oyster Perpetual in that it is classic and understated, yet with a more adventurous history and pedigree. A good choice if you’re on the fence between a dressy Rolex or a sport one.

Where should you buy a Rolex?

An authorized dealer. Period. Wempe and Tourneau are both stellar options.

Whatever you do, do not buy a Rolex on eBay or any other non-reputable place online. Not that all eBay sellers can’t be reputable, but it’s best to be able to actually visit a store to both try a few on and talk with an expert.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

Chime In

  • fishbucket

    I seem to remember you buying your first “rolex” – down by South Street Seaport, maybe ’94 or so. Are you suggesting that wasn’t an authorized dealer? haha

    • http://hespokestyle.com/ Brian Sacawa

      That was actually a Gucci purchased from an upstanding gentleman on Canal.

  • Jason Currie

    That checkered shirt you’re wearing in this!! What?! And where?! I need it

    • http://hespokestyle.com/ Brian Sacawa

      Haha. It’s from Neiman Marcus. I bought it a few years ago.

      • Jason Currie

        I don’t think we have any of those in the UK, damn!

        • http://hespokestyle.com/ Brian Sacawa

          You should check online. I’m sure they ship internationally. If you search for brown gingham shirt I’m sure you’ll find some as well! Cheers.

  • beardedman

    Welcome to the Rolex club Brian! I have a 25 year old “Two-Tone” 36mm Datejust myself, but I am not the original owner. I’ve purchased a couple of other watches – from well respected maisons – but finally felt I was ready for what I consider to be one of the most highly respected watch manufactures along with Patek (though for different reasons). I decided to buy “vintage” because I already had an established connection with a trusted dealer and I wanted to spend a little less so that I would be perfectly comfortable in wearing it every day doing almost anything. So when a pristine, previously owned stainless-and-18K-gold Datejust with champagne dial came along at the right moment, I grabbed it. Many dealers today will service such a watch when it comes in and will offer you a 12 to 24 month warranty for your protection, so it’s not as scary as it once was. It still pays to be careful and stick to the well known places. Bob’s Watches, Crown and Caliber, Govberg and some others are pretty well established these days. That said, there is nothing like “new”. Rolex constantly and quietly improves their products and you will enjoy seeing your own name on the certificate. Walking into a Rolex Authorized Dealer and trying on a number of them is quite an experience, not to be missed. Somewhat like working with a bespoke tailor for the first time.

    DO get it insured with a company that specializes in jewelry. Jewelry insurance is not terribly expensive and it will put your mind at ease when wearing any fine watch out and about or on vacations.

    • http://hespokestyle.com/ Brian Sacawa

      Thanks for the great comment! What a great story. And, yes, some good insurance is a must. Cheers, my friend!

  • Don Steele

    You forgot to suggest The ROLEX Boutique Wempe, in the ROLEX building at 53rd St & Fifth Avenue. Its the largest ROLEX boutique in the USA. They have the largest selection, and Rolex Boutiques are first to get NEW styles.

    • http://hespokestyle.com/ Brian Sacawa

      That’s actually where I purchased mine! They’re fantastic, as I’m sure you know. Thanks for the comment. I believe the BLNR will be my next.

  • Paris92

    Welcome to the Rolex club! My GMT Master II C was a gift from my wife for my 50th birthday a few years ago. I had always wanted that model (The pilots Rolex; originally designed for time-zone traveling Pan Am pilots early in the jet age), as I traveled frequently for work and am an airplane enthusiast.

    We were in the Caribbean on a cruise for my parents anniversary and walked into the AD (Rolex Authorized Dealer) on one of the islands. The shop was about to close (and our ship ready to set sail in 30 minutes) but they welcomed us in. The store staff was working behind the counter and unpacking the FedEx shipment from Switzerland, and out of the packing coffin came my GMT.

    It was the first time I actually had an opportunity to try that exact model on; and when I did it immediately “sang” to me – per many comments on Rolex blogs THAT is how you know it is the right watch for you: It sings to you. My wife insisted that we purchase it as her gift to me (she had been planning to get me that same watch in a few months.)

    I was prepared by knowing the US list price for that model, and when the AD offered a % discount (rare) and no foreign exchange fees or sales tax being in the Caribbean, everything fell into place. The dealer quickly sized the bracelet for me (removing links), we handled the negotiation (discount) and transaction, and we made it back to the ship with five minutes to spare!

    I still get a huge thrill each time I put it on.

  • Tony_Ieradi

    Great article. Thanks. I have been thinking, and thinking, and thinking about buying a Rolex for YEARS!. I have a few nice watches with one of my best being a Tag. I’ve always thought when I get one, it would be vintage as opposed to new. Now you have me thinking!

    Enjoy your new timepiece. I now have more thinking to do.

  • http://www.acsilver.co.uk Gemma Tubbrit

    Although you advise against buying second hand Rolex’s, men’s antique and vintage jewelry is now often sold with a repair and warranty guarantee, so as to ensure the customers happiness and satisfaction with their timepiece. This practice is commonplace amongst second hand watch and men’s antique jewelry dealers, and I would advise caution against anyone who doesn’t offer this service.
    With all antique jewelry, the provenance and status of owning a rare piece is a huge part of the appeal, and adds the thrill of the hunt to the purchase! Anyone with enough money can buy a new Rolex, but it takes a certain amount of taste and knowledge to find an outstanding piece like an antique men’s watch!

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