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The Want: It's acceptable to wear sneakers at many offices, but there are a million options—and most should be avoided. Racing stripes, garish colors, logos, and conspicuous rubber soles send the wrong message: namely, I am not serious. You need a model that works with your office culture, as well as wool suit pants and jeans. It ought to be minimal, a tad formal, eminently tasteful. Dark colors hide stains and dirt.
The Get: The Stan Smith, in matte-finish black ($60 at www.Adidas.com). Made of stiff Argentine leather that always looks smooth and uncreased, it reads as more real shoe than gym shoe, without being overly sleek and fey. Classic.
Bare Ankles: Always wear socks. Plain black or gray, without sporty emblems, are the best for this sneaker.
Cuffs: Cuffed pants with sneakers can look messy and young (in a bad way). Stick with straight legs and dark fabrics.
Dirt: Zero tolerance. The moment sneakers look the slightest bit scuffed-up, they don't come to the office anymore.