With a sense of humor, a playful, bold approach to design, and an affinity for bright colors, David Webb wasn’t afraid to monkey around a little — or a lot, in the case of his iconic monkey pieces. The Gypsy Monkey Brooch was a standout among Webb’s barrel of monkeys — the ultimate playful expression, bringing a smile and a wink to both wearer and viewer. Not one to rest on his laurels, on the heels of winning the 1964 Coty American Fashion Critics’ award, he was already planning his next collection, Renaissance-inspired baroque pearl animal brooches that hit the market in 1965.

The brooches were an instant hit. Fashion writer Eugenia Sheppard wrote about these one-of-a-kind treasures in her article for the New York Herald Tribune, “Pearl with a Belly Button” and quoted David Webb:

Monkeys are a great cult, like frogs and snakes. – David Webb

Marked 'Webb' and '18K' on the back; the monkey set with two round ruby cabochon eyes, each approximately 3.3mm in diameter and the bracelet set with 5 diamonds; made with a collapsible bail so it can be used as a pendant
Measurements: approximately 2 1/4 in. long x 1 3/4 in. wide
Weight: 52 grams
Condition: Great condition with almost no signs of wear. Please see photos for details.