Is “handsome” associated with masculinity and “pretty” associated with femininity? [duplicate]

Yes, calling a man "pretty" or a girl "handsome" sounds awkward and would be seldom used. I cannot think of a single instance of hearing a female called "handsome." In general, saying that a man is "pretty" implies that he has feminine characteristics or is said jokingly.

According to LearnersDictionary.com:

While handsome is more often used for men, women can also be called handsome. When a woman is described as handsome, it suggests that she is very good-looking, and also healthy and strong. Handsome is less likely to be used to describe a woman who is petite or delicate.

The term is dated and rarely used in today's English according to The Urban Dictionary.

The Oxford English Dictionary has this to say of handsome to describe a woman:

Of a person (occas. an animal): attractive and pleasing in appearance, esp. in having a well-proportioned figure and noble bearing; (now) spec. (of a woman) striking, stately, as opposed to conventionally beautiful or pretty

The OED has four quotations that refer to a woman, admiringly, as handsome; one from 1622, one from 1718, one from 1855 and the latest from 1908. My advice is not to use handsome to describe a woman; the danger of being misunderstood is too great.

As for pretty man, instinctively I say no!, but a Korean drama subtitled in English might signal a change. See DramaFever:

The prettiest man in the world is on a mission to seduce 10 different rich and powerful women for his own ambitions. But one adorable and poor girl with a huge crush on him just might change all of that.