Maybe it's just me, but I've always felt that it isn't too difficult for guys to dress well. I chalk it up mostly to a shortage of variety—shirts and slacks haven't evolved too much, I think. Formal occasion? Tuxes and suits. Sure the cut, fit and the way you knot your tie will evolve some every couple of years, but otherwise, men's fashion retains its same basic, sensible essence.
Most men just don't like straying (too much) from the norm. Why else do you think Galliano gets slapped with a sartorial minstrelist label?
Whether you like it or not, if you're a guy, all you've got to do is choose which subculture you identify with and then go pick out the corresponding top and pants.
Hipster? Skinny jeans, narrow-cut shirts fitted at the shoulders. Pray you're skinny.
Urban? Looser, relaxed-fit jeans, larger shirts. Extra points for the squillion-dollar limited-edition sneakers that can only be found in Tokyo.
Dad? Polo T, fitted but not skintight, tailored slacks.
Yes, let's face it: We're all some sort of "type." It's okay. Really!
Like Frank Zappa said, "Everybody in this room is wearing a uniform, and don't kid yourselves."
But the positive thing about all this is that it's not too difficult to stay on top of being stylish. Most of the same rudimentary guidelines that were in place 30, 40, 50, 100-plus years ago are still intact: Have at least one good tailored suit. No cuffed slacks. One pair of black dress shoes, one brown. And never wear white crew socks with dark slacks.
In fact, I'd say white crew socks should be limited to athletic activity. It's tacky to see your white Gold Toes peep out from under your $500 Armani slacks.
Aw, come on. You should be old enough to know this by now.
Your mom? She was right.
If you're a corporate data-entry monkey who feels the need to still retain some sense of humanity despite a fascist office dress code, many of even the most respected, fashion-elite males have been stepping out with fun-colored socks—green, navy, red. Or skulls. Like this H&M navy-on-turquoise pair worn under black slacks.
While it's true that guys lack selection, it's really the little things like this—they're called accessories—that separate you from the rest of the herd.