A Guide To Buying Your First Rolex

Let’s not beat around the bush, buying your first Rolex watch is a big deal. A very big deal. It’s something you need to be prepared for both financially and emotionally. Just over three years ago, I bought my first Rolex–a classic 36mm Datejust–after extremely careful consideration and meticulous research because, well, it was something I did NOT want to screw up.

The entire process took me about nine months and throughout that time I gained *a lot* of knowledge about Rolex watches themselves as well as the emotional arc of going through the process from beginning to end. If you’re watching this video, you are probably very much in the same boat that I was, so I put together my best advice, tips, and questions to ask yourself before taking the plunge into that first Rolex watch.

Top level, there are five things to consider:

1. Why buy a Rolex watch?
2. When should you buy your first Rolex?
3. Do your research!
4. New or vintage?
5. Which model Rolex should you buy?

I dive into each of these questions in-depth in today’s video. And if you care to, you can also read the companion HSS article right here: http://hespokestyle.com/first-rolex-watch-to-buy/

▪ Rolex Oyster Perpetual → http://bit.ly/2qRQKlw
▪ Rolex Datejust → http://bit.ly/2Og8Sn1
▪ Rolex Submariner → http://bit.ly/2qV3eZH
▪ Rolex GMT Master → http://bit.ly/2qWu9Ew
▪ Rolex Explorer → http://bit.ly/2qWFwMr
▪ Shop Rolex at Crown & Caliber → http://bit.ly/2qXvMle

Our friends at Crown & Caliber are offering HSS viewers $150 off their first watch purchase (can also be combined with accessories). All you have to do is use code HSS150! Valid for purchase over $2,000.

Visit Crown & Caliber here → http://bit.ly/2ypEcVV

▪ Favorite Dive Watches for Men → https://youtu.be/vy2B6cCESSo
▪ How To Read a GMT Watch → https://youtu.be/n54Oab-tlls

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▪ Website → http://hespokestyle.com
▪ HSS Shop → http://shop.hespokestyle.com
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▪ Twitter → https://twitter.com/hespokestyle

▪ Jane Lim → jane@wearefoundation.co

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#firstrolex #rolex #luxurywatches


mrg1911 says:

I bought my first new Rolex almost 40 years ago….a Steel Submariner….
Since then I’ve purchased several more.
The Datejust 36 & 41 are the coolest of the bunch.
I have a new 2018 Blue/Red-GMT….but I don’t love it more than my simple Datejust…..or my Explorers….

Crazywaffle5150 says:

Just don’t buy SHITTERS jk. lol. My first watch I just got – 1960s vintage Omega constellation pie pan. Next step is Rolex datejust. Always go second hand in my opinion.

Lord Garth says:

Interesting video. I used to collect watches and do own a datejust but actually prefer some of the lesser known brands. Pricing is an interesting factor. I prefer one that has its value in the craftsmanship and not that it’s solid gold or platinum with diamonds.

Drakotar says:

Prefect timing Brian. I’m looking at purchasing a pre-loved date just for my 21st, great content as always.

Michael L says:

Please stick to one camera angle. The one where you are addressing the camera.

treznorify says:

I’m not a fan of Rolex design, I’m unimpressed with it, except some days ago at the airport, I found some Cellini models in a store, I never heard of them before. Are they unpopular? I hear about Datejust, Subs etc all the time but not these… I could consider getting one as my first Rolex.

Fernando Gomes Semedo says:

There is a third option; buying pre-owned. Watches that would not classify as vintage but usually less than 20 years old. Some are new enough to still have some of the factory warranty left. It has many of the advantages of buying a new watch but without taking much of a hit in terms of depreciation. I’m somewhat surprised that this wasn’t mentioned as Crown & Calibre deal primarily with pre-owned watches. Personally, I’m a vintage guy but I have a few modern watches too. I bought a watch new once but lost a lot of money on resale. Since then, I’ve bought pre-owned. My newest watch is a Speedmaster Professional that the original owner purchased in 2016. He only wore the watch twice in two years of ownership. I got essentially a new watch at a substantial discount. If I were to sell it now, I’d probably make money on it.

thetwopointslow says:

That Datejust you have is gorgeous

Ed Jones says:

I saw a watch on ebay from China. It was a ROW-LEX. #IfImLyingImBuying

gripenM says:

love that datejust, you rock it well! mine is the same but with the black dial. had it for a year now and i still take the time to admire it on my wrist. 🙂

Ragtop Roads says:


Jesvin Varghese says:

TL;DW : Depends on your budget and preference.

Ryan Maher says:

Would an oyster bracelet really be considered more casual than a Jubilee?

Always felt it was the opposite way around.

David Williams says:

Great video and comments. Your suggested pieces were spot on. Thanks

Bo Stark says:

Impossible to buy one new even if you want to.

Frederick Calabrese says:

A watch, even the vaunted Rolex, isn’t an investment. If I make a certain level of production, I’m buying an Oyster Perpetual.

MarcoD says:

Great video mate! I’m gonna buy a 36 Jubile DJ as well, but I’m not sure yet about the dial color (either silver or black). What do you think about the black dial and its usability?

Raff Time says:

Great video and choice on the color and bracelet combination .

JayH says:

Not very informative through the first few minutes, so lost my attention.

Pablo Sánchez says:

Great video!. Do you think the smooth bezel goes well with the jubilee bracelet, instead of the fluted bezel?

J Lo says:

Step one: pick a watch

Jay Atwood says:

The explorer for me for sure.

Alan Lau says:

I’ve inherited my late grandad’s Datejust 36 watch and i love it so much! Its 2 tone with jubilee bracelet, fluted bezel, and roman numerals with diamonds on each marker on a houndstooth patterned dial too which i find is stunning. I do agree to buy new is the best but a pre-owned or vintage timepiece from your family is something else!

Edward Wiot says:

What are your thoughts on the Cartier tank?

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