Watch Help Needed!

Ys more or lss one for formal wear and one for casual unless you're never formally dressed.

Dress - Seiko or Citizen
Casual - Suunto or G-Shock

Can't go wrong!

As an Italian, I've been wearing Swatch watches. They add a touch of zing and color and, although they are plastic, many work well with formal wear too. My favorites are the "skin" ones, that is, the superflat ones. An example for formal wear would be:
http://store.swatch.com/core-bestsel.../page/1/SFK361
http://store.swatch.com/core-bestsel.../page/2/SFK360

For casual, there are models that are fun but not too out there eg:
http://store.swatch.com/core-unisex/...s/page/2/GB261
http://store.swatch.com/collectibles...page/1/SUOZ126

Incidentally, re the suits you were showing. The plaid ensemble looks typically southern, so it's fine if you live there. Remember that you can wear white trousers only between memorial and labor days. This rule is set in stone. If you don't live in the south, it'll be very hard to make it work other than at church and at weddings. But the suit is fun and I like its green, so I'd say it'll work well with some light colored pants (eg light green?)

cacio

I said I grew up in Italy... we don't mind paying for fashion; the swatches are interesting and quirky, so they demand a high price even if they are plastic. (But they seem to be appreciated even here, I've been complimented many times about my "skinny" watch).

Yes, the rule of no white-not only on pants but also on suits and shoes- outside of the allowed period is absolute, unless on vacation in seaside resorts. We don't have this rule in continental Europe, and I learnt about it when I moved to the States.

As for the other suit, it seems a more classical pin striped, good for all occasions. I would personally go for a more discrete stripe, but it's hard to judge from a photo - sometimes photos increase the contrast. But I don't dislike plaid suits either - they're nice and informal and I have one myself, but on the tones of light brown. The difficulty with the one you showed is the ivory background- white is difficult to pull off. With a non-white background things would be easier.

cacio

Oh Italy. Those guys put the rest of us to shame...

I just bought a new watch as it happens, an ESQ Movado, all-black chronograph, at the Movado Factory Store at about half price. I like large chronographs and wear them all the time but the big chunky ones look a bit too flashy for me in standard stainless.

I really like the Movado Bold series, which you can get at upscale department stores like Saks, but they are probably out of your price parameters. There always seems to be lots of watches on sale at every price point at Amazon.com.

I've always liked the idea of a dress watch and a regular watch but essentially I buy one (water resistent to at least 5 atm) and wear it all the time until I get tired of it or the battery runs out. I have two or three dozen stopped watches in a drawer. I work in an extremely dressy place my and new watch works just fine there. In the U.S. you can wear pretty much any watch that isn't too cheesy or outright ugly these days in most situations. I would never wear a digital at work, however.

BTW I wouldn't say the white rule is sacrosanct everywhere in the U.S. anymore (e.g., maybe not in California and other semi-Mediterranean, anti-Eastern establishment locations) though in my neck of the woods it sure is. Current fashion in the northeast seems to be for dark and neutral colors and very tight, minimalist styling and tailoring with the most subtle patterns, if any. (Looks very early '60s to me.) I've been wearing a lot of black and notice that's what's in the stores. I always wear simple black rubber-soled Oxfords, not too shiny ("priest shoes" a friend calls them) because they go with almost everything. You are still supposed to wear brown shoes with a gray suit but even my gray ones are pretty dark.

Forza Italia mia paisano.

An additional belated suggestion: so far, Tissot watches have never let me down, a good brand at affordable prices

I admit, their range of sporty and complicated models is still limited, but in terms of dressy and daytime wear, as well as formal wear watches, they are hard to beat within their price range

The Movado Bold series is quite reasonable for a Swiss made watch. You can also see them and order direct from their website, which I think is just www.movado.com.