For example: here we see a Brooks Brothers trifecta in this combination of tweed 2 button sack ($3.00), vintage repp tie ($1.00), and white oxford button down ($3.99). This combination of thick tweed, and skinny tie paired with that mystically inimitable "roll" of a Brooks Brothers collar is about as old as it gets.
I like these clothes, and I like to wear them. But I'm a not a student at Yale in 1965. My job far from requires that I dress this way, but still I choose to. By changing one element for casual, in this case jeans for flannels, I manage to wear these things without coming off like a pretentious jerk or a costume party joke. The same transformation can be managed by simply leaving the tie at home, or wearing a parka instead of a top-coat sometimes.
I don't want to "dress up" like 1965. I don't want to "dress up" like a Polo ad. But I will observe both these things, take what I will from them, and try to blend them, and myriad other cool things I've seen, into some unique combination of my own. You should too.
Learn from what you see, don't copy it, and above all, take it easy. It works out better that way.