Can we get some short hair Ws going to combat that?
I'll start with
I Made Friends with the Second Prettiest Girl in My Class. In this one there's a long-haired "rival" for "best girl", but the short-haired one "wins".
Kinda looking for stories where both are present, but the short-haired girl is chosen, and not just stories where the FMC is shorthaired.
(Edit: I get that the one I recommended doesn't quite fit (unless you're aware of
future events), but I'm looking through my completed entries and only finding ones where the short-haired girl loses

.)
I personally really love girls like Shizuku, but they practically always lose. Frustrating, really. Especially when they lose to such generic and boring "pretty girls" like Ayaka.
At this point I'm ready to take visual novel recommendations, too, since those tend to have multiple routes where you can actually
choose the best girl.
I remember really liking
Aoi Isuzu from
Hoshizora no Memoria -Wish upon a Shooting Star-, though I almost forgot everything and it, so it might be time to replay it.