As you already know, I enjoy buying, owning and wearing well made and distinctive clothing. As you may have noticed, fewer and fewer men's lives require or, dare I say it, even permit this kind of dress on any sort of regular basis these days, my own not excluded. Now this isn't to say we all need to succumb to the abject laziness of un-tucked shirts, sweat pants and un-shaved faces that is all too prevalent among the grown men of today. Conversely, dressing like a stuffy old man and constantly grousing about it is neither stylish nor cool, it's grumpy and, at best, quaint. Better to find some middle ground, even if you're version of middle leans a bit further toward your grandfather than your son.

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.

Down below, rigid denim
Wranglers, J. Press socks and Florsheim longwings. Now I can almost here the purist among you crying "why didn't you wear some flat front grey flannel pants?" True, the addition of grey flannels would make this outfit completely classic, almost to the point of a mid-sixties Ivy League nostalgia. So why wear the jeans? Simple: because grey flannels would have brought this outfit into the realm of mid-sixties Ivy League nostalgia.
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.