Ecko Unltd Shirt, Plaid Major Payne

The tiny windowpane check design of this dress shirt exudes classic sophistication with modern flair, tailored for a regular fit from the always dapper Michael Kors.

Keep it simple. Stripes step up the style on this shirt from Izod for a piece that can easily transition from work to the weekend.

Paired with a crisp pair of chinos or denim, gingham is classic summer wear. These sharp shirts from Girbaud do not disappoint.

Button down front

Long sleeves with button cuffs

Small pony logo on pocket

A tonal patch pocket adds to the casual appeal while chambray fabric inside the collar provides a secretive pop in the U.S. Polo Assn. Plaid Woven Shirt.