Known as "The High Priestess of Fashion," Diana Vreeland single-handedly orchestrated fashion's history, mostly before noon from home by dictating memos to her assistants. In Diana Vreeland Memos: The Vogue Years, her grandson, Alexander Vreeland, compiled more than 250 pieces of her irreverent personal correspondence to notables from Richard Avedon to Valentino. Perfect for the style cognoscenti. Barnes and Noble, $55

Tom's new wedge series adds some heightened style to your ethically sound shoe collection. Especially love these, crafted with jacquard woven tribal-inspired patterns that will easily serve as your fashionable Florida winter bootie. Pink & Navy, $84

Made in Italy and constructed from 100 percent Italian wool, this Psycho Bunny woven plaid scarf in charcoal and red is a not-so-basic accessory that will signal he has cooler-weather style, but doesn't take himself so seriously. Jackie Z Style Co., $85

If you can't play with fashion, what's the point? This whimsical "Misbehaving" word jumble is a charmer fashioned of cotton and cashmere, with slits at the side hem and dropped shoulder that creates just the right amount of comfort for errand day or movie night. Evelyn & Arthur, $214

This modern reinvention of the classic boutonniere is a subtle way to add a touch of flair to his look. Crafted from the world's finest fabrics from velvets to leathers, these stylish lapel pins by hook+ALBERT are handmade in the Big Apple. Each unique flower comes equipped with an elegant shell button for attaching to the jacket's lapel. Neiman Marcus, starting at $26

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This article appears in the January 2014 issue of Sarasota Magazine. Like what you read? Click here to subscribe. >>