For casual outfits (jeans and a t-shirt or casual button shirt), a leather band watch and silver stainless-steel watch are the best option. The leather band watch is one of the most casual watches available for men and some are digital as well. This gives off a very laid back and trendy look and feel. If you want to have a slightly sportier look while having some type of dress code, a stainless-steel chronograph watch is universally accepted to match with the majority of outfits. For the most part, these watches are water proof since they are sporty and casual. They match with most daily outfits and are functional enough to meet your needs.
For slightly dressier outfits, such as office attire, leather band watches do not cut the criteria and you should look for black stainless-steel watches or for a more mature look, a gold watch. A black stainless-steel unlike a white stainless-steel watch is more conservative and dressy. These watches can be all black but a popular design is the all black white with a dark blue background face. For an older, mature look, a gold watch or dual tone gold and silver accented watch is great. These are fantastic for outfits that are primarily slacks, dress shoes, and tucked in dress shirts, with or without a tie.
For formal occasions such as weddings where a tuxedo or formal suit is worn, the best watch is the one that is the least flashy and most subtle. The subtlety is what makes it fashionable. An example is a black skinny leather banded watch, with a black face and gold bezel, with minimal designs on the face. A watch like this creates a subtle, stylish look and is perfect for formal occasions.
No matter where you wear the watch or with what style you choose to go with, use your confidence to pull off a look and remember that for a stylish watch, being subtle is key.