Matt writes:
I got 2 nice looking black button-down long sleeve dress shirts this past week, one I bought at a thrift store and one I received for Christmas. I just realized I have no idea what pants/belt/shoes to wear them with. Can you go all black? Should I go instead with a khaki trouser or a blue pant? What about if I’m wearing a tie and sport coat?
Black is one of the most difficult colors to wear successfully. It has a tendency to make even the richest of complexions look sickly, it is near-impossible to pair with anything, and no matter how much you think you look like Johnny Cash, unless you’re one of the greatest popular musicians of all time, you probably look like a low-rent Eastern European mafioso.
So, when and how can you wear a black button-up shirt?
To start with, don’t wear a black shirt with a tie. Don’t wear it with non-indigo blue. You can try it with dark denim for casual events, especially in the evening. You can pair it with mid-grey slacks and black shoes for marginally dressier casual evenings out. You could add a contemporary, fashion-y grey sportcoat to a black shirt and dark jeans and look vaguely like Giorgio Armani. You can add a beret for performances where snapping is preferred to clapping. You can layer it with other black pieces for Skinny Puppy concerts.
And, uhm, that’s all I can think of. Hope that helps.