I've studied two of his plays - 'The Merchant of Venice' and 'King Lear'. To be honest, The Merchant of Venice is quite easy to follow, but is also a bit boring. King Lear, however, if one of his most complex plays but is actually very captivating with a good plot and some witty humor. :)
His works honestly haven't aged that well if you ask me.
It depends what you like. 'The Tempest' is an excellent example of his mature style. 'As you like it' for his earlier period. Some plays are more straightforward like 'Coriolanus' and some wander a bit like 'Troilus and Cressida'.
But don't read them, watch the BBC productions, they did them all and have subtitles if you have trouble following the language. They are old and the video quality is poor but the acting is good to excellent. Of watch Laurence Olivier's films of 'Richard III', 'Hamlet' or 'Henry V', he is superb.