Watch  

I own a Tag Huer Monaco Le Mans replica and an Omega Seamaster silver. I love both and wear both on a regular basis. I think my favourite watches would be Pateks, but they are WAY out of my league as of right now...

That's a pretty high-end watch collection. If you get tired of any of them feel free to send them my way, especially the Patek  

Although I have a Patek 5107 in white gold, I am currently torn between the IWC Mark XV and the Cartier Roadster (which is a bit more expensive).

Given a choice between these two watches, I would not hesitate to go with the Mark XV.  The Roadster, in my opinion, is too "bling bling" while the Mark XV exudes understated elegance that can dress up and down equally well.  I have often thought about getting the Mark XV white dial, which is more elegant (if less traditional) than the black dial.  The one downside to the Mark XV is that 99% of the general public will not know it is a high-end watch, but I think most IWC owners prefer it that way. Currently in my watch rotation are a Glashutte Original PanoMatic Date, a Blancpain Aqua Lung, and a Raymond Weil Parsifal Quartz.  One or two more and I'm done -- this hobby is way too expensive.

I'm no fan of Rolex watches -- but do you think diamond watches on men are any more refined?.

AC - you are mirroring my sentiments. I am leaning towards the white faced, buffalo strap, Mark XV. Everytime I pass it, I try it on. I think that I may splurge this weekend and get it (I have found it on-line for less than $2000.00).

This of course begs the question -- Why do you own a Rolex, particularly one made of platinum with diamonds?

Shucks, A Harris had to call it first. I doubt that the majority of people seeing a calatrava with a leather band would see it as a high-end watch. I can see the point, but my wife bought me a Rolex as a present when I finished my MBA.  And it wasn't new money, it was hard saved money scrapped together when she was a starving law school student.  I don't think I would tell her that it was too brash.  Then again, it is not solid gold with diamonds. -Andy

Lawyer: Get the Roadster. I love that watch. You're a young guy and that's a cool-ass watch; it would look awesome. The leather band looks better that the metal one, plus you need the face with the grren and orange numbers. The IWC is too frumpy.

Different strokes for different folks, I guess.  I must admit that my choice of the Mark XV over the Roadster was based in part on my bias against jewelry companies that make watches (Cartier, Chopard, Bvlgari, etc.) and my taste for more traditional, understated designs.  That said, the Mark XV is indisputably the better made watch.  To use an analogy: the Roadster is like a Versace, fairly well-constructed and flashy that says "look at me," while the Mark XV is like a Brioni, impeccably constructed and hardly likely to earn a second glance except from fellow connoisseurs.  The Roadster's main advantage is its ability to garner raves from beautiful women at a club -- something GQ Lawyer will hopefully not be seeking given his marital status. If it matters, I have read that the white dial Mark XV is being discontinued, to be replaced by this flashier silver-dialed model.  It may be difficult to find in a store in the future, although it will be available on the secondary market.