Dated? Goddard comes to my mind.
Goddard's films appear to be very dated, specially Breathless.
Some of Hitchcock's films are also quite dated, such as Notorious (I mean, it was considered all normal back them for a men that look's 65 to marry a woman that looks 25?, Vertigo already suffered a bit, given the male protagonist was about twice the age of the female (49 to 25, actually)).
Another film that felt really dated for me was Casablanca.
Breathless to me felt like a film made by a director attempting to create something fresh and new, very stylish and 'cool', obviously it Godard was quite important in revolutionising cinema and the film would have impacted on a lot of others, so it's feel will have been reflected in a lot of films since, so maybe it feels dated in that way where as it might have been more 'fresh' at the time. But I still found it very cool, it's the only film where I have seen such unusual jump cut editing.
Vertigo I wouldn't say is dated, it's main strengths are in the themes it deals with with the characters, and for me the ages are not important, masculinity, domination, obsession etc. are all issues that a lot of people find important and are still very relevant today, it's a very personal film and this can be felt, it's risen over the years in terms of critical appeal and was recently voted the top critics film of all time, so I would say that it is definitely not dated.
Casablanca feels like it was made in the era that it was, yeh, but I would say most Bogart films do, this is not a bad thing though, I love the old, stylish feel of them.