No watch, either small or large, is going to "date" a person's look imho, unless you are pulling a pocket watch out of a waistcoat. Hairstyle, makeup, clothes and shoes are way more important and always grab my attention first. So, if your clothes, hair, and makeup are up to date and stylish, a smaller 26 mm watch won't doom your overall look one bit. So, I say wear your 26 mm Rolex, maybe stack a couple bracelets around it occasionally, and enjoy the heck out of it.
Totally agree. I am also laughing because while I totally agree with what you said, the pocketwatch line made me think of Big Bang Theory when Sheldon buys a pocketwatch, Penny says he looks ridiculous and he replies, “Nonsense, I look like a train conductor.” So even the pocketwatch might not date you lol.