Well, here's the thing: I don't think unmatching socks are unboring. They are just good aesthetic sense. No one will ever be shocked by solid maroon, brown, or navy blue socks under your grey flannel trousers. And they don't "compete" with complex shoe finishes any more than socks that match your trousers.
On the other hand, socks matched to trousers grab attention for all the worst reasons. They're fastidious, neurotic, unimaginative, and geeky. The man who matches his socks to his trousers is either too boring to waste time with or repressing too much violent rage at an overbearing mother to be safe around. In either case, he probably thinks Big Bang Theory and Two and a Half Men are funny. He definitely keeps a calculator with him to figure out tips. He's that guy who holds up the line at the supermarket because he pays with personal checks. He's an asshole and a bore.
Don't be that guy.
In all seriousness most people shouting here do not deserve the guidance and thoughts from this real gentleman
It's admittedly hard to judge combinations like this because they are so cliche. Very JoS. A. Bank.
But to be as objective as possible, here's whats wrong: (1) the contrast gap is too large, with all dark, saturated colors and nothing in between to bridge them, (2) discounting grey and white, you're only wearing one color (red), which not only makes for a boring outfit, but makes your tie loud and distracting, (3) unless wearing black tie, white shirt plus white square is an auto-fail, even if many will argue it is 'correct', and (4) the tie is an intrinsically ugly iteration of paisley due to its lack of tonal variance. The overall effect is a real-life simulation of a cartoon businessman drawn by an artist limited to three different crayons. Not good.
Oh I agree ... just changing the color isn't sufficient to bring a look alive. It takes experience and a good sense of color.
Originally Posted by mafoofan
The man who matches his socks to his trousers is ... too boring to waste time with
Here I would disagree. I was recently at a dinner party with political economist Robert Reich. His socks matched his trousers ... and he was anything but boring. On the other hand he's not one of the best dressers.