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Let’s assume both pieces have an awesome patina and the only difference is that one is pristine and the other has scratches, marks and other imperfections. I always choose the worn one because it has character unlike the pristine one.
Relic condition > mint condition, at least for leather.
I think it's normal, as some people prefer a more "rustic" aesthetic, and believe that blemishes add character. I tend to enjoy it on some things, as well.
I still have tons of my old leather horse tack from my horseback riding days, and I have to admit, I prefer the look (and feel) of well broken in leather over brand new. Most of my saddles are older than me and have some imperfections in the leather, but like you said, they add character! I especially like leather that doesn't have a color-corrected finish, because it has a richer look to it when it isn't a single monotone color and very "perfect" looking (plus, much of the color-corrected stuff has a cheap "painted on" look and doesn't take oil, so typically doesn't ever have as nice of a feel, and rather than looking better with use/age, it tends to wrinkle and the color sometimes wears off weirdly in places). If possible, I prefer completely un-dyed leather (though it's pretty hard to find these days now that the trend is for everything to be dyed a dark Havana brown, plus dye hides imperfections in hydes) because it always tends to age the best, and have the best look and feel to it throughout the years. I actually have a couple of bridles that started out really light and didn't darken the most evenly (not blotchy or anything, but just a bit lighter or darker in certain areas depending on which pieces have seen the most use), but I think the difference in color looks kind of cool.
I also played the violin many years ago, and it was very common for violins to be "antiqued" when they were made, meaning dings and scratches are intentionally put in the wood, and it is stained in a way to make it look old and worn. It is considered a desirable quality because of the character it adds, and typically only starter violins look "perfect" with no blemishes (until they get their own throughout the years, of course). They are very plain looking in comparison to the "antiqued" ones.
Most people prefer worn or distressed leather because its more flexible and more comfortable to wear.
Looks depends on the event, just as with all other clothing. You look best at some events if you have pristine leather, and fit in better at others if you don't.