As a well-dressed gentleman, you should always match the formality of your watch with the formality of your outfit.
A dress watch is the most formal of all watches, and therefore, it’s the one you should wear to formal events, or whenever you need to dress your absolute best.
So, what should a dress watch be like? It should be simple (with no excessive features or decorations); elegant; small enough to fit comfortably under your shirt and jacket cuffs; and it must have leather strap with soft, thin leather (no padded nor chunky ones).
Bear in mind that you should match the leather of your watch and belts and shoes: black watch band – black belt – black shoes. Brown watch band – brown belt – brown shoes.
The texture and finish (glossy or matte) of the leather must also be matched.
And the metal case of the watch should be coordinated with the metal accents of your other accessories (cuff links, shoe buckles, belt buckles, or other jewelleries).