Menswear tends not to change that much, which can be both a blessing and a curse. It's a blessing in that certain things can last you a lifetime, like this combo here, if you buy quality to start with. It's a curse because things can get drab real quick if you let them. Such clothing can easily wear like a uniform. Throw a patch on the jacket, it's a school uniform. Throw a different patch on it and you're the hotel concierge. The best way to avoid this is, I think, to use tiny details to give it some style, without losing that classic edge.
I'll frequently use a plain white or blue oxford button shirt with a jacket and tie combo like this, but a contrast club collar worn pinned pushes the dressiness level up a notch, without getting out of hand. (Shirt by Brooks Brothers, Italian fabric, made in USA, $4.99)
The very conservative two button cuff of this 3/2 undarted blazer is given some punch by the less conservative two button shirt cuff.
The die hards are gonna twist and turn, but the reverse pleats on these pants break the conservatism another pinch, even though this is an old way of styling pants. I'm generally a flat front guy, but the more time goes by, the more I find myself digging the double reverse pleat. In a year or two these will be fashionable, mark my words. After so many years of being told to avoid pleats like the plague, the fashion industry is bound to tell us the exact opposite anytime now. Never mind all that, it's a styling detail that hails form the 1930s, and it is at home in any tasteful mans wardrobe. (Wool flannel pants by Polo, made in USA, $7.99)
Nothing could be more conservative than brown Florsheim longwings ($20). Striped socks (Target, $5.99 in a package with two other pair) act like navy socks, only more fun.
Classics are classics for a reason, and they're best worn with an understanding of tradition...only, don't be afraid to tweak 'em. The difference between a stylish take on the old rules and rigid conformity is all in the details.
