premise: A man with a beard sits on a bench with a cloak and fancy hat. hypothesis: While wearing a fancy hat and cloak sits on a bench stroking his beard.
entailment: Both sentences say that person is sitting on bench.  The first sentence says that the man has a beard and has a cloak and fancy hat.  Having a cloak and fancy hat is one way of saying that these items are being worn, which is what is stated in the second sentence.