例句-1：Did you hear that new comedian on TV last night? He is not very funny.He takes too long to tell his jokes and they are all old chestnuts that I heard at least a dozen times before.
College就是大学;try在这里就是努力的意思。把old college和try三个字组合在一起就成了一个习惯用语。它的意思是，尽最大努力去做一件事。在三十年代的时候有一些描述大学足球队的电影非常受欢迎。 Old college try是学校里的学生为自己的球队加油时说的话;也就是鼓励正在场上比赛的队员尽力踢好这场球。很快这个说法就变成了日常用的口语。
下面是一个例句。这是一个爸爸对女儿说话。他的女儿正准备去上大学，还想参加女子篮球队。
例句-2：Barbara, think seriously about trying out for the basketball team.In high school your team went to the final for the state championship and if you make the old college try, I am sure the coach will pick you for the team.
Comfortable在中文里的意思就是舒服;shoe大家知道就是一只鞋子。要是你有一双鞋子，虽然已经穿得很旧，但是因为你穿得很合脚让你感到很舒服，所以你还是很喜欢它。你大概可以猜到这个习惯用语的意思了吧。Comfortable as an old shoe就是指你已经很熟悉的人或一样东西，因此让你感到很放松很自如。我们来举个例子，例句里说话的人在讲多年来住在他隔壁的邻居。
例句-3：Joe is a good neighbor, as comfortable as an old shoe.He is always cheerful and friendly and on summer evenings, we like just sitting around on his porch, enjoying the fresh air.