Cherries are cute and red.

I like cherries (esp in RL) so if that dress had shown up in any other episode I wouldn't have given it a second thought. But in an episode screaming "SYMBOLISM!", it's different. I'm actually not crazy about this episode - or at least I like everyone else's dreams but by the time they got to Buffy it was the first time watching the series I actually said aloud "Bored now". (And I was by myself in the room.)

I prefer it when the show weaves the symbolism in for me to find, instead of marking it out with a great big neon sign. (Of course the house falling down in Smashed isn't exactly "subtle" but it still allows for a variety of interpretations as well as the literal level of the story itself. Dream sequences don't work on a "story level" because they are outside the story. I think Dead Things is a masterpiece, but I'm not as crazy about the "dream sequence"; the entire episode has the feeling of a fever dream so ironically sticking a dream sequence into it feels off.)

she wears another cherry dress in The Freshman

She does? I'll look for that on rewatch. I think S4 is extremely underrated.