Photographs by Brad Bridgers. Gucci ($510), gucci.com.
Unlike its predecessors, the newest incarnation of the checked shirt skims the body and the arms, even when the sleeves are rolled up. Super-lightweight cotton not only makes the button-down a fresh alternative to a polo but also looks good pressed or rumpled. Courtney Colavita
The Check: The smaller the plaid the more refined the shirt, especially when paired with a knit tie. A shirt in a larger pattern or equipped with Western-style snaps is best worn outside the office.
Two-Tone: Plaid comes in hundreds, if not thousands, of varieties. When in doubt, keep it simple. A two-color pattern is at once subdued and graphic. [A.P.C. ($150), apc.fr; John Varvatos ($225), johnvarvatos.com]
Bold: Most men can't get away with wearing a solid red shirt, but a button-down with prominent strokes of the vibrant hue is appropriate for just about anyone. [Original Penguin ($79), originalpenguin.com; AG Adriano Goldschmied ($138), agjeans.com]
Muted: Your first instinct might be to balk at a lavender shirt, but when pastel tones like lilac and pink are used in plaid, they become much more palatable. [Gant ($195), 212-206-3928; Gap ($50), gap.com]