I've said it before, a watch is the single most important accessory a man can own--it is an essential style element. As you might imagine, I am acutely aware of these kinds of details and I must say I've noticed too many casual watches making their way into office/work/formal settings. It screams sloppy (and so do I) and I urge all of you who wear your multi-function sport watches with your suits and other dressier attire to pick up something slightly more sophisticated.
First Consider Your Lifestyle
I do suggest having different watches for both work and play if your lifestyle merits it or you simply like having variety. However, when buying a dressier watch, you should choose something that is classic or more lasting. I'm not as concerned about sporty/technical watches since they have a tendency to be less expensive--such as those made by Nike, Suunto and Polar. And let me be brutally honest, there's nothing stylish about them anyway - they are about function. Now if you have a sporty watch like the Omega Seamaster, that's a different story. Can we say James Bond?
And just to clarify, if your watch has a night-vision feature, measures distances, calculates altitude, has a compass, has a rubber strap, and/or has a digital display, it is the wrong thing to wear to a more formal occasion be it the office, a more formal party, etc.
Here is a list of things to consider when looking for your watch.
A Stainless-Steel Bracelet
Stainless steel is more practical than leather and is certainly more durable. It's dressy enough to be worn with a business suit and casual enough for other occasions. So not only is it versatile, but it's waterproof to boot. You could always go for gold if you wanted to drop some serious cash, but be careful since it might give off an unfavorable impression.
Another thing that gets me when it comes to watches is the size of the watch face relative to the wrist that's wearing it. On bigger men a standard watch face can end up looking like a ladies watch. Watch makers are continually coming out with watches that have larger than standard faces. In fact, it has become quite a trend. I personally love bigger watch faces whether you're a big guy or not, it's a great look.
It's a great feature if you shower or swim with your watch on, but let's be honest, who really does that? I like it because if you get caught in the rain or get your watch accidentally wet, you don't have to worry. And by the way, water resistant can mean several things so be sure you ask to what degree the watch really is resistant. Some watches will resist moisture from accidental splashing, rain, sweat, etc. and others will resist moisture up to certain depths such as 50 or 100 meters.
The Color of the Face and Strap
There is a trend to have dials and straps in exciting colors. I've seen it from cheap to expensive watches. When building a classic wardrobe stick to the tried and true colors that you know will blend and look appropriate in a business or formal setting. Save the trendy colors for a second or third watch if you must.
And if you need some help choosing a watch, I have put together some great suggestions - My Favorite Watches for Men Under $300, My Favorite Men's Watches Priced Around $1,000 and My Favorite Fossil Fashion Watches for Men.