The Best Entry Level Rolex Watches – 4 Classy Options To Last A Lifetime – $2000 to $4000 (WWT#85)

In today’s WWT episode (wristwatch talk) I am joined by the right honourable and fellow Explorer brother GCR (Giancarlo). We talk Rolex and have a closer look at 4 extremely classy Rolex watches from his own collection. When it comes to buying luxury watches, Rolex is very hard to beat. Undeniable universal recognition, outstanding quality, value retention, iconic in design, and a rich heritage of innovation only a few can compare to. However, for many, this legendary world changing brand may seem unaffordable or beyond most people’s budgets. Today I take a look at 4 lines of Rolex that are attainable from $2000 to $4000 on the used market, and even a few new pieces too! In this video we take a look at a few excellent examples including the DateJust (Ref. 16030), an AirKing (Ref. 5500), an OysterDate (Ref. 6694) and of course my very own Explorer (Ref. 114270).

For more information and to get your horological questions answered, join our UGWC community on the Facebook group:


TGV’s Tumblr:

To contact me please email:
I do not use the messaging system on YouTube, Facebook or Instagram. Thank you


DonjonArmory says:

Nice video. I have a love hate relationship with rolex. I do also, hate the cyclops. I still think I want to eventually buy a Rolex however.

kassu_ says:

Would love to hear your opinion on hanowa watches especially on the flagship model if you have any experience with it. Im new regarding this whole watch game and just discovered your chanel. Great content!

fuchtler 10 says:

Besides the rest…the intro was gorgeous!


You done with Rolexes? Haha! I don’t believe you either TGV. Great video and enjoy seeing you guys talk watches. Keep em coming! Thanks!

Luigi Casoli says:

Holdest rolex more than pure, modern

Whytech01 says:

Hi TGV, great video as always. I’m visiting the U.S. Soon and I wanted to know if the second hand market is cheaper there than here (in the UK), thanks.

Kyle says:

Love how you two feed off each other, really awesome to watch, high quality

mibolefthanded says:

my dad pass his datejust ref 16234 s/s white gold to me as a gift. I tried googling it but not much information i can get, is there any link or maybe you can do a video about the 16234? Looking forward to it. thank you…

Love your videos…

eddy borges says:

The more I watch your videos the more I use your watch experiences and use it as a reflection of my subconscious. I lust after some of these high end watches and then watch how you explain the nuances of your love and hates.

It has saved me probably thousands in irrational impulse buys for watches I lust after.

I look at my collection and really appreciate the watches for what they are. My Omega aquaterra gmt is the priciest of my lot and the dozen of my Japanese pieces are enjoyed just as much, thanks to your channel.

Daniel Herrera says:

Awesome video TGV. Can you do a review about the Rolew Oyster Perpetual entry level you speaked about? the one
with the purple dial and roman numerals. Thanks

william banks says:

Love the air king series! Also a big fan of John carlo! I’m also lucky enough to own the new air king, beautiful piece. Also wasn’t a fan straight away but after buying it, it’s so fun and great history

oscar gustavo arcos ruiz says:

TGV your wife is Mexican? So, she is my paisana 🙂
Greetings from Mexico.

brian connolly says:

great video on some very classy pieces. some great banter going on there too!

Ryan Doppelganger says:

Favourite affordable Rolex would be a 1603 or 1600… no quick set date but a nice vintage piece

Michael Ogden says:

Love this

HoHos says:

Hello TGV, I am looking to buy a watch for my dad’s 60th birthday and I’ve only got 350-400 usd to work with. I was looking at Seiko SARB-033 because that seems to be your favorite entry level automatic watch. Do you have any recommendations for a watch that is slightly nicer than the sarb033 for extra 50-100 dollars or so?
Love your channel and thank you in advance.

Daniel Wang says:

I’ve been looking at Rolexes as well, I’d like to add another watch to this list! Take a look at the bubblebacks from back in the 40s, they look amazing. Great video btw, always good to relax to one of your videos!

bonustraka says:

when we will see the first Richard Mille model on this channel ? I want to see the reaction to one of the perfect models of Richard Mille.

Julio Aparicio says:

You guys make a great team on camera. Keep them coming. Saludos Giancarlo.

Patrick Lundy says:

Love your show! I dont buy a watch until you’ve given a positive review of it

Mario Morciano says:

“Daje Daje Tristano questo orologio è perfetto per te” (cit) LOL I’ve almost choked laughing 🙂 great episode guys! Thanks for sharing your passion with us as usual.

qazaqsha obzor says:

Hello to all my friends! I’m selling watches Panerai Luminor Power Reserve Pam 90 44mm Automatic Men’s Watch! Price: 3500$

Gordon Evans says:

I hit the like button before the intro even started. Hilarious!

weerobot says:

I’ve got Schwarzkopf disease….Thanks TGV…

hervé Chretien says:

Love the format of this video and the sound has improved over previous one, which is nice. One piece of advice to first time Rolex buyers, toying with the idea of forking out some serious money, but not over 3 grands , for the privilege of having the Crown on the dial : think really hard about it before pulling the trigger. If your real, deep in your mind dream is to have a watch people recognise as a Rolex 20 feet away, Tony Soprano like, may be the vintage smooth bezel DateJust is not for you.

Nick Stefan says:

Hey,The Urban Gentry! I love your video! I know this comment is marked as spam,that’s because it contains a link. But please check out this video and approve the comment!

Tim Schubardt says:

Great video. My favorite Rolex is the Datejust because its the most iconic and versitale Rolex in my opinion.:)

HC Gaming says:

I spend a fair amount of time on YouTube but your channel is the first that I actually look forward to new videos! I am only 15 and have recently purchased my first Swiss watch – a Tag Heuer Formula 1 2015. I enjoy your videos as they’re very informative and pure class! It’s a shame that there are not many others in my age group that have a passion for horology as I think that it is a fascinating hobby and interest. I guess I’ll have to wait until I have a bit more money for my sickness to live up to its full potential though! By far the best watch channel on YouTube. Thank you TGV!

Chris Lomas says:

I have a 1986 Oysterdate and I love it, gets a lot of wrist time, great to see you talking about them.

sidney scotchman says:

I been seeing a particular looking watch for sale almost every where I look the last few months…but have not seen any reviews on it, Brooklyn Waterbury Sports Diver Black Dial Swiss Quartz Watch 302-M4113.. have you come across this watch before? Usually see the regular price tag at $500+ in stores but their “sale” price has it slashed down to $100. Usually I just call it marketing fluff that makes items seem more valuable then they actually are. But I’m curious on this one because it says rose gold plated bezel and sapphire glass. Im not planning on getting it, but I seen it enough that it peaked my interest.. especially since I have not seen any online reviews.

Wito Techmatic says:

I like your channel and your videos Tgv. You kind of remind me of Howard Huges or something, i hope you do not take it badly, you always seem so happy, and that is good,  and you have a interesting family heritage or how they say, i have seen some of your videos, and also seen you on your  fb group. Good that you love watches and does this as a hobby or whatever. Rolex is out of my price range, i was looking at one many years ago, do not know if it was real or not maybe it was made under license, i saw it somplace abroad, i remember i loved the quiet movement of it. If one can afford it why not. I like my Casio, lol. 🙂

Harsha Deshpande says:

Great to see good old Rolex watches passed on from generations! Good to see you my friend Giancarlo. Always a pleasure to hear you talk passionately about watches and football (especially AC Milan ;))

stephen rhodes says:

My favourite is still my first, the Rolex Datejust. I still have a bit of a soft spot for the Explorer but no other watch will ever top the feeling of getting the first.

Regarding the cyclops, one with & one without is the perfect combo i feel.


Excellent Video Chaps!! I could watch you guys talk Watches for hours!!! Keep the momentum going Fellas!! BMJ ENGLAND

cristiclaudiu says:

I have to say this..this is slowly becoming Rolex Channel and I don’t like this

 Write a comment


Do you like our videos?
Do you want to see more like that?

Please click below to support us on Facebook!