I can't remember if I've posted this elsewhere, so apologies if folks have seen this before.
My guidelines are generally drawn from basic rules of style, which can be summed up as: character, contrast and formality. For each new watch I generally commission a specific strap from one of my favourite craftsmen (e.g. Mr. Haidukoff) or small strapmakers (e.g. Finnwatchstraps). They're only slightly pricier than buying from a larger distributor and, hey, you wouldn't wear cheap shoes with an expensive suit, so why have a cheap band on an expensive watch? That having been said, I wouldn't spend more than £75 on a band (my average is around £50), as beyond that, the payback of price to quality seems to drop off. But hey, if you have the dosh, and you want an
exclusive strap by Mr. Fancypants, knock yourself out.
As with any other style rules, these can be bent, but it's best to master the basics before moving on to more advanced stuff. These rules also apply to shoes (in fact, they're based on that). NB: The buckle metal should match the case metal, always.
Step 1 (character): ask yourself "what kind of watch is this?" A dress watch needs a formal strap, a dive chrono a sporty one. So example one, a Le Jour Triton in a ref. 2002 case with a ZULU strap:
Step 2 (contrast): With one exception, it's a mistake to get a strap whose main colour matches that of the watch dial. You wouldn't wear brown shoes with brown trousers, would you (if you do, you should stop)? Instead, match light dials to dark straps, dark dials to light straps. It's fine to match the
secondary colour (e.g. contrast stitching) to the dial or a dial detail. The one exception is black-dialed watches. These go
best with black straps, though sportier ones should have some contrast to make things less formal (see the Triton above). But you can also go cognac, or dark brown. White or cream dialed watches are complemented by cognac, mid-brown, or dark brown (not black). Example 2, a Lemania HS9 with a mid-brown Thoroughbred ZULU w/cream stitching (again, this also follows rule one, a military watch with a military strap).
Step 3: Formality. This is really an offshoot of step 1. The general rule here is: more detail = less formal, plainer = more formal; larger = less formal, smaller = more formal; thicker = less formal, thinner = more formal. This applies to watches
and bands (and shoes). Anything with a bezel is, by definition, less formal, as are most chronographs, since they're
designed to be used for sailing, racing, flying, diving, etc., none of which are activities that (unless you're James Bond) merit formal dress. Again, tastes differ, but I've always thought that a big metal bezeled chronograph worn with a suit is not really the thing--you can get away with it, but why would you
not wear a simpler dress watch instead?
Applied to bands, this means that a thin simple band with no contrast stitching is formal (e.g. a flat cordovan band), while a thicker band with texture or stitching is informal/sporty. The one exception to this is exotic skin bands (sans contrast stitching), which are formal. So, example 3, a Ranchero on a flat Teju lizard band:
It's worth noting that Rancheros were originally more "sporty" watches, since they are on the large size and have rather sporty batons, but for our purposes, it will suffice. Formal/informal is a relative matter.
So, some of the other points raised here are also answered by these rules. Of course, you should generally match thicker cases with thicker bands, but a really beefy one with contrast stitching will make the watch
very informal, while a thinner or plainer one will make it more formal.
One last rule of style: leather bands, like leather shoes, should come in either black or some shade of brown (of which there are
many, from pale tan to espresso). On very rare occasions, navy or dark grey is justified. Bright colours may be "fun," but they will never be elegant. If you're wearing a bright orange rubber watch band, your other articles of clothing should be a towel and bathing trunks. Also, it's very difficult to follow the final style rule of accessory matching (see below) if you have a multicoloured band.
What is that final rule, the surest sign of style-awareness? The band should match the belt should match the shoes!