Though it's been gathering steam within the style set, a short sleeve dress shirt is still a bit tricky. At best, the look conjures images of nerdy NASA flight-directors; at worst, schlubby bible salesmen. But thankfully, there's a wide range of options now that are as classic as they are cool. "I think the bad connotations simply come from bad versions in the market," says designer Matt Singer, who helped build Jack Spade before launching his own line last year. For summer, he created a short sleeve oxford cloth popover. "I spent a lot of time getting the right fit across the chest, the ideal sleeve length and the perfect hand-turned collar to strike the right balance." To ensure you don't veer off into Dwight Schrute territory, a few pointers: You want a shirt that's trim, with sleeves that hit mid-bicep. And if you're going to be showing your arms, make sure there's some muscle tone there. A tie's not out of the question. Just embrace the preppy heritage and choose a retro cotton or madras option. "I wear them under a suit, with a pair of 501s or on a warm day, with shorts," says Singer. "It's really the most versatile shirt I own."
$195, by Matt Singer