Sandra Hamburg in her early nineties Jean Paul Gaultier blazer with faux-monkey fur collar.   (Photo: Courtesy of Sandra Hamburg)

Nothing is more ephemeral than fashion. Right? Wrong. With patience and a good eye, fashion can be an investment. A black crocodile Birkin bag, for example, sold for $64,800 at auction in 2005. The key is knowing which designs in your wardrobe will appreciate over time and which are destined to fetch $5 at Andy’s Chee-Pees.

One very well-dressed woman agreed to see what her fashion collection would bring on the cold, hard auction block. Sandra Hamburg, an artist, photographer, and one-half of the ironic rap band Mother Inc., is a true mixer who loves no-name thigh-high boots as much as the black Gaultier fur-trimmed jacket that set her back $700 in 1991. She’s also fortunate enough to have had a stylish, label-loving mother who passed down vintage sixties Yves Saint Laurent and Pucci in good condition. So the five floor-to-ceiling closets in Hamburg’s floor-through apartment-cum-closet in Greenpoint are bulging with unique pieces.

Clair Watson, director of couture at Doyle New York auction house, assessed Hamburg’s collection recently. While Hamburg bounced her 3-month-old daughter, Nico, on her hip, Watson—who sees some 100 closets a year—dug in with a combination of clinical appraisal and personal enthusiasm. “Sandra’s clothes are about ideas,” said Watson. “She doesn’t have to wear the latest fashion or spend a lot, and yet she presents a strong identity as a creative person.”

After two and a half hours of sifting though dresses, jumpsuits, coats, sweaters, shoes, bags, and belts, a few lessons emerged. First, anything bought new immediately drops in value, usually by two thirds. Second, labels matter—but what matters more is getting an instantly recognizable piece from the height of a designer’s creative powers, like a fifties sculptural evening gown by Balenciaga. Third, designers age like wine. Early-career pieces by Christian Lacroix, John Galliano, and Jean Paul Gaultier are especially valuable at the moment, whereas Tom Ford is still too recent and too easy to find. Fourth, current trends have an impact: Thanks to the return to prominence of sixties styles, Hamburg’s taste is exactly what collectors want right now. Fifth, it’s better to spend time rummaging through sales and thrift shops—Hamburg’s favorites include Beacon’s Closet and, in Miami, Sasparilla—than to pay the jacked-up prices of retail. And last, take care of your clothes: Stains, alteration, and perspiration drive values downward.

Hamburg turned out to be one of the rare women who could probably make money on her wardrobe. What follows over the page is a cross section of her collection, accompanied by comments from Watson. The original price paid is listed—often at thrift stores and sales, which is why so many of Hamburg’s buys seem like bargains—followed by Watson’s estimate of auction value.

PAULETTE BURAND ORGANDY DRESS
Year: 1969
Paid: $75
Value: $75
Clair Watson’s appraisal: “That graphic is great, but it isn’t well made and the label is obscure. This is a quick fashion piece.”

PRADA TAN LEATHER SKIRT
Year: Mid-nineties
Paid: $400 on sale
Value: $300
Watson: “There’s a lot of respect for Miuccia. She’s like Gaultier—there are people looking out for older pieces. This is too new, and it’s ready- to-wear.”

CASADEI ROMAN SANDALS
Year: 2001
Paid: $300
Value: $100
Watson: “This is not a label that one looks for at auction. But it evokes Capri in the Dolce Vita days.”

APRÈS-SKI CARDIGAN DRESS
Year: Seventies
Paid: $80
Value: $100
Watson: “It’s Gucci revisited, isn’t it? It’s an idea piece, but it’s not good quality and there’s no label.”

GUCCI WOOL TROUSER SUIT
Year: 2001
Paid: Unknown
Value: $300
Watson: “Tom Ford’s impact on fashion was all about sexuality, and this just isn’t a good example of that.”

SONIA RYKIEL LEATHER BAG
Year: 2001
Paid: Gift
Value: $200
Watson: “This bag had a lot of press when it came out, and it was the first of its type—the studded bag, revisited. It might fetch even more at auction.”

RAINCHEETAH WITH SILK STITCHING
Year: Sixties
Paid: $40
Value: $300–$400
Watson: “This kind of style with this kind of color always does well at auction. The shape is so Marc Jacobs. I love it!”

YVES SAINT LAURENT MOLESKIN HELMET
Year: Mid-to-late sixties
Paid: $60
Value: $200
Watson: “Saint Laurent wasn’t known for this design, but it’s in rare condition for something of that period.”

CHARLES JOURDAN RAFFIA PLATFORM SHOES
Year: Seventies
Paid: Inherited from mother
Value: $300
Watson: “A wonderful mix of inspirations. Jourdan is a great name from that era. These pieces will gain in value.”

CHLOÉ SILK KNIT SHEATH
Year: Circa 2002
Paid: Unknown
Value: $200
Watson: “I love this sleazy stuff. But nobody really cares yet that Stella McCartney was the designer.”

MAUD FRIZON SUEDE PUMPS
Year: Eighties
Paid: Inherited from mother
Value: $100
Watson: “Maud Frizon shoes are collectible, but these are not the extravagant style that we know and love.”