Play It Smooth

After perfecting their popular button-down oxford, the gents at San Francisco-based shirtmakers Taylor Stitch started thinking about a shirt that could be easily dressed up on days that called for a tie. And that meant something as comfortable as it is versatile—like Japanese milled cotton (in gingham or bengal stripes) with a slightly shortened spread collar and a lower side gusset for tuckability. "We've always been a fan of English dress ... we love the spread collar and it's most pronounced with nothing else going on in the front of the shirt," says co-founder Michael Maher. "Take away the pocket and smooth out the placket and it creates really clean lines." To make the lines even cleaner, they removed all the usual pleats from the back and sleeves. "We find them superfluous and our whole design perspective boils down to simple functionality—pleats just made the shirt baggier and harder to iron."

Bengal stripe shirt, $165 at Taylor Stitch

• How to Iron Your Shirt: We asked Thomas Pink's studio manager for a detailed, yet uncomplicated guide to the perfectly ironed shirt.