I don't dislike it, but to me it does have a bimbo image, and also a downmarket image. It's also dated, but not the same way that I think
Mary or
Anna is dated. mary and
Anna seem dated because they've been so popular for so long that they seem not so much dated as "default" names.
Heather, along with
Brittany, are dated because they were so wildly popular in such a small window of time, and fell so fast.
Ashley and
Madison have also been popular within a fairly narrow window of time so far, but they haven't fallen anywhere near as fast as
Heather and
Brittany.
Heather doesn't seem fresh either, to me anyway. So many Heathers are of an age to be having kids themselves.