A customer just asked about the best sneakers to wear with our jeans. Obviously, the options are limitless, however, I like to wear them with a simple classic sneaker that looks fashionable but not too trendy.
Converse Jack Purcells in white and blue, the Adidas Stan Smith with the green tab (pictured) or the Adidas Campus in the medium blue with white stripes, for example, all look great and are appropriate across ages. The common theme with these suggestions is they are models that have been around for some time and remain mostly unchanged from the original issues. All of these work with chinos as well.
I am amazed at where I find myself wearing sneakers now. When I put on a blazer and tie with my jeans, I can wear sneakers almost anywhere—to dinner, the theater and even a dinner party. The other great thing about sneakers is they are relatively inexpensive so you can by a couple of pairs or refresh a pair when they get a little worn or dirty.