I hope it's ok if I chime in as an extremely biased source!
In theory Chloe is pretty dated, but in actuality I've only ever met one other Chloe who was a few years younger than me, in her 30s. No little Chloes! Mostly I hear about dogs with the name. Chloe to me has the same energy as something like Emma, Charlotte, Isabella, or even Sarah (from my own generation) - an ancient name dragged out of the depths when trends changed. It feels like a dated trend to a lot of people right now, but in the grand scheme of things, it's really not, it's a super old name so it has greater "timelessness" than something like Kaitlyn or Madison or Lauren, yeah, I agree with you there. I totally understand what people mean when they say Chloe is vapid and ugly and all that, I really do. But the crispiness of Chloe is the crustiness of time, not just flimsy candy coating. I'm not sure if that....helps.
I wouldn't be surprised to meet a baby Chloe at all. I wouldn't be wowed, because I like unexpected names and obviously I see my own name every day. But it's a fine name! The middle name can really add chicness or dial up the trendy datedness too, imo.