Honoré de Balzac once wrote “Carelessness in dressing is moral suicide,” but we know that if carelessness is the number one sin, a bit too much carefulness is not far behind. There are the two ever-present opposite concerns of looking disjointed or ill-conceived and appearing a mannequin with everything matched to a fault. The key, as with all things menswear (and truly all things in life) is balance.
Now, don’t get ahead of me and think I’m advocating another contrived form of sprezzatura or offering up a “how to dress well in a world that generally doesn’t” guide. Those things can be important, but what I’m getting at here is a much more basic aesthetic principle – what you wear at a given time should harmonize, whether through unity or contrast.
A perfect example is colorful accessories. Typically a gentleman has four places for flexible color in daily attire: tie, handkerchief, cufflinks, and socks. Looking like you bought the foursome as a box-set from the discount bin is about the last thing you want. The habit of matching is tempting at times though. I personally have an orange handkerchief that I rarely wear except with a certain orange and navy tie I quite fancy. No one’s perfect. Often though, choosing things that are complementary colors and patterns results in a much better look than choosing things that obviously match. The result has more depth and interest, rather than a single note. Purple tie, burgundy socks. Orange handkerchief, purple silk knots. The combinations keep on going. That is not to say matching can never be done, but at least try to vary tone and texture to keep things interesting.
You also don’t need to make all four of these elements a statement all at the same time. A pair of somber socks can keep a bright tie and handkerchief from looking comical, while a plain navy tie can set off those striped socks you want to wear without distracting like more stripes might. A striped shirt with a spotted tie might look great, but if you throw in a printed handkerchief and some wild socks, the whole thing begins to look a bit overwrought. Balance between fun and foundation is key, and as always, the overall look should be greater than the sum of its parts.