Yes, practice helps you refine your guess - photographic styles change over the years - fashion, hairstyles, tech - big world changing events - wars, the pandemic, the 1970s oil crisis.
Also the importance of zooming in on details - a movie name, a date on something, a famous face.
You learn bits of history.
You remember pics that get shown fairly often - that little boy in #5 shows up regularly (I was still years out).
With all that, we have blind spots - sports, esp motorsport are one of mine. And wars have a tricksy habit of not being the one you first thought of.
tl:dr yes, practice helps.