No'l Coward may have introduced the turtleneck to the middle class in the 1920s, but by the '60s it had taken on a sartorial subversive bent, and the rolled collars had become the signature of stylish radicals. Cotton turtleneck by Tommy Hilfiger, $148
2. Sole Man
A Manhattan sleuth like Mister Tibbs must be stealthy and stylish. With these graceful and slim loafers, Poitier could walk the red carpet or a dark street. Air Rivington Tassel by Cole Haan, $245
3. The Thin Black Line
Poitier predated bling, but one can't help but think that even if he hadn't, he'd prefer a clean, simple, classic belt and buckle to the diamond-crusted Jacob the Jeweler ones seen today. Leather dress belt with brass buckle by Brooks Brothers, $88
4. Hip to Be Square
Only Poitier could make the pocket square trendy. Tucked into this relatively unstructured beatnik pureDKNY blazer ($325), a white linen square by J. Crew ($38) lends an air of dignity and quiet formality.