Unless told otherwise, it would have been impossible to guess the year that this photograph was taken. It could have been 60 years ago, when a young Jacqueline Bouvier rode horses in rural Virginia, or it could have been last summer on a Long Island polo field. This timeless look brings a sense of mystery and sophistication to the otherwise simple combination of a white shirt and khaki pant. A raw silk blazer adds opulence; a cashmere throw lends sumptuous utility. Rugged riding boots add character to otherwise crisp pieces, creating an unexpected contrast. The secret is all in how you wear the ensemble: Trim, fitted shapes, luxurious fabrics and a muted palette segue beautifully from the bridle path to the office as long as they are worn with poise and self-confidence. That sort of classic glamour, as Ralph Lauren himself once said, never goes out of style.