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first rolex watch to buy
first rolex watch to buy

A Guide To Buying Your First Rolex

May 11th, 2016

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

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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