Let me start by saying that these are not hard and fast rules. You won’t be shunned by society and ostracized because of your watch style. This is meant to show that different watches can augment and the way you can achieve a perfect style.
Let’s start by going through the common types of watches.
Normally they are a simple watch that shows the hours, minutes, seconds and maybe a date. Usually a plain white or cream face with no fancy additions. Usually with black leather strap.
A diver watch usually has a simple face with a movable bezel. This was so that divers can keep track of the amount of air in their tanks. It can have a steel or rubberized strap.
Chrono / Sport Watches
These watches have all the bells and whistles. Some even have GPS capabilities. These are meant to track time, be used as a stopwatch and other functions where accuracy is important.
Driver / Pilot watches
Usually having a larger face so that the wearer can quickly see the time and other information displayed by the watch.
Which with What
Wearing a tuxedo or other formal look demands a dress watch. Simple yet elegant plain face watch with black strap.
A simple watch with very few extras. A dress or diver watch would be fine but always a leather or natural skin strap.
Any watch you choose will be fine here. Thye setting is less formal and you want to appear relaxed. All the main categories of watches fit here.
Like business casual, you can wear any watch with metal or natural strap. metal is more casual so it really is up to you
Wear your sports watch with metal or rubberized strap. make sure your watch is designed for the activity. Dress watches are not suitable for sports activities.
Matching Watch Style
This comes down to simple rules of thumb. Keeping your outfit and watch in harmony the rule is leather to leather and metal to metal.
If your shoes are black and a belt is black then a black leather strap is suggested. A metal strap will go with the black leather in silver. If your shoes are brown then opt for a brown leather or gold metal strap. Earth tones with earth tones.
Your watch style really does depend on your tastes. Certain occasion call for more refined watches and others call for something more robust.
A good watch will last generations and the straps you choose will make or break your outfit. Try having several straps that can be changed on your watch to match your dress.