1) Watches - The less gaudy, the better. The less complicated, the better. Men do not wear much jewelry, so people read a lot about you by your watch. Here's some advice.
This is probably the best looking watch I've seen for 2010 style - a vintage Rolex California. These are also cheap for Rolex standards. The band should match well with the face and with your shoes. I really don't think men need to be anal about matching a watch like this with their shoes, but if you want to go the extra mile, then here's a simple rule - a black band, black face, and stainless casing (or a totally stainless watch which a black or white face) will always match a black or gray outfit. Brown or navy outfits generally look better with brown bands, white faces, and a muted gold casing.

Here's a Rolex Cellini. These are the Rolex dress watches and I've seen many go for good prices.

Chunky is ugly right now. The only chunky watch that is currently fashionable is a Breitling with a leather strap.

Some other watch ideas are:
* the old Tag Heuer S/EL - used, $350
* Vostok Amphibia with rubber diving band and no bezel - $75
* the old Tag Heuer F1 used, $275
* Black/SS Rolex Submariner (older and thinner the better) - used, $2,000
Are you getting the hang of this? CLASSIC... OLD>NEW... SIMPLE=BETTER.
2) Jewelry - The easiest rule here is, if you are married, wear a ring. If you wear a ring, it should be a simple band and should be white gold or platinum, preferably. After that, a soft, worn gold is cool. "Simple" is key. Simple is in. Women even want smaller, simpler rings these days (thank God). Showing off your wealth is uncool right now, but style is always in. Wearing any other jewelry is not really fashionable unless you stem from a culture that is rather ostentatious, and then it is OK. I'm sure you'll ask about wearing your class ring. Save your college street-cred for your resume or when someone asks in idle conversation.

3) Sunglasses - There are basically two types of glasses that always look good in casual and work situations - Ray Ban classic Wayfarers (dark tortoiseshell looks awesome) and Serengeti Medium Aviators.

Ray Ban started it, but Serengeti perfected it with its polarized, gradient lenses (Ray Ban later started using this style of lens in its aviators, and now it is difficult to find these in stores).

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