And, knowing it's New York, if I noticed him, I would have probably seen him and thought, "this guy looks like Henry Cavill and is trying to make a few bucks in Times Square with tourists" Which is kind of a thing in Times Square.
All of the "clark kent" level disguises are completly immersion breaking.
Instead "ooo she doesn't know he's the awkward newspaper guy she's in love with" its "my god woman, are you blind? All he did was take off his glasses and put on tights yet you can't regonize the man"
She just has undiagnosed face blindness. So she just goes off of people's behaviors, and since Clark has never turned into superman in front of her she doesn't realize it's the same person.
This is why I loved the Christopher Reeve characterization... His Clark acted differently, walked into doors, bumbled, stuttered, somehow seemed smaller and less characterful. Every time someone says, "oh stick some glasses on and he'll be unrecognisable" I think of those parts, and... Yeah, just about possible.
They made a joke about that in the Scooby Doo and Krypto Too movie. When Velma takes off her glasses neither Lois or Jimmy recognized her. It was corny and tongue-in-cheek, I loved it.
This scene for me (you can skip to 1:20 or so) showed that it's at least feasible, but it definitely takes a lot more than glasses, which is where many of the non Christopher Reeve's portrayals fall flat. They always play Superman in both roles but it's just Superman with glasses.
Christopher Reeve on the other hand showed that Clark Kent is the perfect disguise when portrayed correctly and it's at least understandable that especially the people that know Clark would never suspect for a second that he's Superman because they've never seen anything but a quiet, weak and easily frightened man who is nothing like Superman at all! Superman is also way taller!
Watching him stand up straight and put some confidence on his face, voice and transform into Superman over the course of 10ish seconds was one thing, but watching him deflate back into Kent in under 2 seconds was another altogether! That shift was jarring for me and showed just how good the disguise was and how good of an actor Reeve was.