How to Buy Your First Rolex – A Gentleman’s Buying Guide

A Rolex is often the first product men want to buy to reward themselves for hitting a milestone. A classic watch such as a Datejust or a Submariner can help you recall that achievement for decades to come. Regardless of your opinions on Rolex, there’s probably no one out there who would argue that a good watch collection is complete without a Rolex watch.

Rolex has been a cornerstone of the entry-level watch market for decades. It has a sterling reputation for robust reliable watches. If you select the right model in stainless steel, it will increase or at least maintain its value. Furthermore, the consistency of Rolex models, with only slight changes over the years and decades, make it a classic timeless timepiece that you can wear for years and decades to come. So why should you buy a Rolex and conversely, are there reasons not to buy one?

How to Buy Your First Rolex

Many people who are interested in buying a Rolex are not necessarily watch aficionados, but they are familiar with the brand enough to take the plunge and get a nice watch. That being said, watch culture can be quite intimidating because there’s so much discussion around it. Sometimes, it can feel unwelcoming because people argue so passionately about things that they like but also dislike about Rolex. If you leave all that behind for a moment, always keep in mind that a Rolex is first and foremost for you, the wearer. It’s not like a car that you typically share. Yes! You can hand it down to your son, but most of the time, people don’t share watches, they just wear them

In this day and age, it’s less of a timepiece and more of an accessory. You have to wear and like it, and that’s all there is to it. So let’s take you through some steps that make sure that you end up with a Rolex that you will love and want to wear for years to come.

Step 1: Ask Yourself Three Key Questions

Is a Rolex a good fit for my personal style and how will I wear it?

Rolexes may be ubiquitous, but do you really like the style of Rolex or is it just the brand name you’re attracted to? How often do you want to wear this watch? Is your style more dressy or more casual? All of the watches that made Rolex popular and famous are sports watches or professional watches, not dress watches. They aren’t intended to be worn with suits and formal outfits, even though many people do. That being said, in this day and age, a lot of people wear their stainless steel GMT Masters, Submariners, or Datejust with suits. 

Can I afford a Rolex?

A Rolex has a high price tag and it’s important to consider the cost before buying. Honestly, it’s not a good idea to just put it on a credit card and pay interest on a fashion purchase. Save up some money, and buy it proudly with cash when you have enough. 

Am I buying this Rolex watch for the right reasons?

Are you buying it for yourself or for others? Do you just want it because it’s a status symbol or because you truly like the look? Are you really going to wear this watch frequently? At the end of the day, you should only buy something that you get a lot of wear out of because that way, the cost per wear is really low. 

Once you’ve honestly answered all those questions, you can move on to the next step.

Step 2: Choose New, Pre-Owned or Vintage 

A new Rolex is pretty straightforward; you pay full price, you get your authentic product, you get the boxes, the papers, and everything there is. Buying a new Rolex will give you peace of mind but you’ll also pay a good chunk of money for it.

Now maybe you are like me and you like vintage things; you appreciate the patina of an old leather strap, or the slightly worn-in look that a watch gets that has been worn for many years. In that case, a vintage Rolex watch could be something for you. Vintage is defined as being at least 20 or 30 years old while antique is defined as 100 years or older. For many years, vintage Rolexes were not popular, but in recent years retail prices and interest in watches have spiked, leading to a subsequent rise in interest and the prices of vintage pieces. 

The third category is pre-owned Rolex watches, which are watches that are less than 20 years old. Overall, this is probably the most cost-effective price segment because the vintage watches sometimes go up in price because a specific model is rare or sought-after. Pre-owned Rolexes, on the other hand, have probably the best value ratio between wear and discount. Of course, as I mentioned before, pre-owned and vintage Rolexes may be counterfeit watches or have counterfeit parts so keep that in mind.

Step 3: Choose Your Watch Details

Watch Size

Start with a size of the watch case because size definitely matters in a watch. We believe that the size should always be proportional, just like anything else in classic menswear. If you have a slim wrist, you need a smaller watch. If you have a big wrist, you need a bigger watch. Overall though, I think there’s a tendency to get bigger and bigger watches so even if you have a bigger wrist, I would argue to stay clear of the oversized watches above 41-millimeter case size because they also get thicker and wider; the look is flashy, chunky and decidedly inelegant. 

Most men interested in a Rolex will fall between the 36 mm and 41 mm case size. If you have really small or slim wrists, a 34 mm size may be right for you. Again, if you have a big wrist, 41 is the max I would suggest you go with. If you are not sure what size watch is right for you, keep in mind that the watch should cover about two-thirds of the width of your wrist. To learn more about watch sizes for your wrist check out the guide on our website. Now, if you have a slim wrist, some models like the Submariner which only come 40 mm may not be the best choice for you.

Material and Band

Next up, it’s time to choose the right material and band. For Rolex, I strongly suggest you go with a stainless steel watch case and bracelet, simply because that is in line with the sporty character of the watch. It also happens to be the most sought-after material, it resists age exceptionally well, and it retains the most value.

If for some reason you like the two-tone look of stainless steel and gold, go for it. In that case, I suggest you maybe try the vintage market because gold is a lot more expensive at retail, so the initial price is higher. On the pre-owned and vintage market two-tone is less desirable, so the vintage prices are below the stainless steel. If you want to get a Rolex Daytona in gold or platinum, go for it. It’s likely not going to be a bad investment.

Bezel and Dial

Once we’ve chosen the material and the band, it’s time to look at the bezel and the dial. It’s your first nice timepiece or your first Rolex, we suggest to stay clear of flashy colors or bold details simply because it makes your watch less versatile and you likely will wear it less often. Of course, if you’re an artist or if you love color and it’s part of your personality, by all means, go for it.

The old adage is “light with light,” meaning choose a light face for daytime and a dark face for the evenings. Now I would argue that it’s easier to wear a light face in the evening than it is to wear a dark face during the day. That being said, it’s just a rule of thumb. 

For example, a Submariner only has a dark face and it will still look good if that’s the style you want. However, if you want a light face, watches like the new Submariner or a GMT Master II are not an option because they don’t have a light face in stainless steel.

Step 4: Choose the Right Model of Rolex

When you’re just starting out, you may not be aware of all the different watch models that Rolex is offering and frankly, there’s quite a few. If it’s your first Rolex and you want the classic sports watch, I recommend you pick between a GMT Master, a Datejust, a Submariner, a Daytona, and maybe a Sea-dweller for value. The Explorer or the Milgauss are cool alternatives, but they’re not as likely to retain their value.

Regardless if you buy the current or vintage Datejust, Submariner, or GMT Master, they will look very similar to ones that are twenty or thirty years old or even older. That is a strategic choice by Rolex, and buyers can be comforted knowing that no matter how old their watches are, they will change very little in the way they look and feel.

The Datejust is probably the best option if you want to wear a sports watch to the office with your suit. If you like the look at the Datejust but you don’t like the Cyclops magnifying glass over the date, go with the Oyster Perpetual. It’s often not recommended because it is so simplistic, but I believe that makes it a really great choice with clean simple lines and a very classic profile. It won’t win you any awards for uniqueness but it’s a solid first choice.

If you prefer a bigger watch, the Explorer or Explorer 2 with a 42 mm case may be the right choice as they are sportier. It also has a cool history because it was issued by Rolex after Sir Edmund Hillary summited Mount Everest in the 50s.

The Rolex Daytona or Cosmograph Daytona are a full-on chronograph. Ironically, in the early days, it was not a very popular watch but these days, it’s the most expensive one in the lineup. Paul Newman’s Rolex Daytona was auctioned off at $17.75 million. Personally, I think that Daytona in steel with a white face is not as sporty as it might seem and it could be a cool option if you’re interested in that model.

If you like sporty watches, check out the Submariner, the GMT Master 2, the Yacht Master or the Sea-dweller; all are good options for a first choice and even better for the second addition to your collection once you have a basic watch covered. I’d argue that they’re all a little big and bold for a first watch, but of course, that’s just me. 

Step 5: Do Your Research, But Don’t Go Down the Rabbit Hole

Watch research can be tough. There are very strong opinions out there about very minute details, but at the end of the day, it’s about you. If you’re someone who researches extensively, then by all means, go ahead. After all, you’re spending a lot of money on this timepiece but keep in mind, it’s very easy to fall into a Rolex online watch hole.

Now, if you keep coming back to the same timepiece in your research over and over again, then it’s probably the right watch for you. Also keep in mind, even though a particular model may not retain its value as well as others, if you love the watch, you can never go wrong. At the end of day, do your research, don’t go overboard, and don’t let others make the final decision of the watch you will wear.

Step 6: Go to a Physical Store

There’s pretty much an authorized Rolex dealer in every city. Go there, try different watches on, figure out what your favorite is, and then leave. Do not buy anything on the spot, just leave and go home, wait a few weeks, maybe a month, maybe two months, and if you still want that watch, that’s a good indicator that it’s the right watch and that you’ve made your decision.

Step 7: Buy from a Reputable Dealer

There are endless ways to buy Rolexes, but for such an important purchase with many highly accurate counterfeits in circulation, you should buy your piece from a reputable dealer of new, certified, pre-owned and vintage Rolexes. 

You can buy vintage Rolexes from trusted online places such as Theo & Harris or Bob’s Watches. I would advise you to stay clear of eBay, other forms of auctions where they sell vintage watches where you can’t examine things or any kind of small-scale dealer that’s not a specialist. You want to deal with a volume dealer in Rolex who has a reputation on the line, who wants to continue their business and selling Rolex. Otherwise, you just may end up with a fake because it’s very likely and if you’re new to this, you may not even spot it and think you’ve got the real deal.

Conclusion

With all that being said: good luck purchasing your Rolex! Keep in mind that studies have shown, men who buy one Rolex are statistically very likely to buy a second one, and even a third!

Are there any pieces of advice you think we missed when it comes to buying a Rolex? Share with us in the comments below.

Outfit Rundown

Today, I am wearing a Rolex GMT Master with a blue and red dial and have dark face in stainless steel. I also chose cufflinks in Lapiz Lazuli with sterling silver and a carnelian in sterling, and because they’re red and blue they work well and are consistent with my watch.

My jacket is a double-breasted petrol blue fresco jacket that is part of a suit. Here, I’m wearing it with a pair of dark brown and white seersuckers and a woven leather pair of penny loafers. It’s a very summery combination, because of that, I added a white shirt with a knit tie in a mottled gray, which is from Fort Belvedere, and you can find it in our shop here, just like the white Italian linen pocket squares with hand-stitched or embroidered little dots which works well with my outfit. It picks up the white of the shirt as well as the blue the GMT Master and my cufflink.