What tops and shoes can I wear with a pair of chocolate brown chinos?
Congrats on opting for a pair of chinos, and bonus points for going the chocolate brown route. Khakis are thick on the ground, and Nantucket reds are proliferating at a rate I endorse (not entirely due to the fact that they basically necessitate accessorizing with a Dark and Stormy), but their cocoa-hued brethren seem to have gotten overlooked.
The first thing, and perhaps the most obvious point, is this: Leave all other browns in the closet. You don’t want to be mistaken for the UPS guy (note: nothing at all against employees of the United Parcel Service). You probably have a variety of brown tones in the footwear department—leave them be. White is probably your best bet. The canvas sneaker is always a great option, but how about opting for a pair of red brick-soled white bucks? There are a lot of them out there, in a range of price points, from Cole Haan to Alden to Epaulet.
Above the waist you’ve got a variety of options. A heather gray V-neck tee would do just fine for a casual day of errands. To dress things up a bit, try a button-front shirt with a lighter base fabric. Can’t stress this enough: Do not wear a dark shirt. This includes black and cobalt. A lighter-colored shirt, say off-white, with a subtly textured check pattern would offset those dark pants and contrast nicely with the white bucks you’re (maybe) sporting. A light chambray is also a nice option here (emphasis on light).
Keep fighting the brown fight.