>>725168832 (OP)
Societal trends (which includes fashion) and the evolution of art is why. Combine that with the evolution of film and tv as a medium (which is inferred when I said art). It used to be that styles from the 20s through to the 40s (zoot suits et al) and speaking a certain way, were shorthand for things like mafioso through the 80s and early 90s. That shorthand was carried into modern (for the time) gangsters. They were in most cases well dressed suit and tie types in the "modern" (for its time) day.
Unfortunately (fortunately) by the time cartoons, movies, and videogames were aping that, the mafia was already past its peak and was on the decline.
Organized crime has gotten more legal so to speak. By the 90s mafioso weren't dressing especially gaudy of flashy anymore. Hoodie, jeans, track suits and bowling shirts were in. Even then bowling shirts aren't really shorthand anymore because it's twenty twenty fucking five. Tracksuits also don't work in current views unless it's an Eastern European styled mobster.
As for sexy women, we still have those, but it also depends on the type of game you're playing. Most games today aren't about getting the girl or a kiss at the end.
TL:DR
These visual cues are nice, but extremely outdated. They can be pulled out every now and then, but it would be a bit "cringe" if they were used in earnest without A. Being self-aware or B. Paying homage.
