Top 10 most iconic silks in racing history

1. The Phipps Family Stable

All black jacket, with a cherry red cap, the colors were registered in 1932. Classy, simple, understated − and they've won a race or two along the way, too: Buckpasser, Personal Ensign, Easy Goer, and Inside Information are only a partial list.

Ogden Mills "Dinny" Phipps, son of Ogden Phipps and current keeper of the flame, has added a dab of cherry to the jacket's cuffs to denote the distinction.
In the 1988 Breeders' Cup Distaff, the Phipps silks were hardly distinguishable in the muck of Churchill Downs as Randy Romero brought the undefeated Personal Ensign from far back to beat Winning Colors by a nostril.

"I had Winning Colors measured," Romero said afterward.

He was the only guy in the joint who knew that.

2. C.V. "Sonny" Whitney

Eton blue jacket, brown cap. In 1898, the Earl of Durham's horses had a case of the slows, and he had a bad case of the shorts. His silks were among the oldest in English racing, and William Whitney, Sonny's grandfather, coveted them. He asked the earl for his price.

"You can have them," the earl said. "They've been of no luck to me."

The silks traveled well. Harry Payne Whitney, Sonny Whitney's father, bred and raced Regret, the first filly to win the Kentucky Derby, and in 1984 Sonny Whitney, who bred more than 175 stakes winners and raced many of them, passed on the colors to a nephew, Leverett Miller. Marylou Whitney, Sonny's widow, won the 2004 Belmont and Travers with Birdstone, who raced in silks similar to her late husband's.

3. Calumet Farm

Devil's red, blue collar, two blue hoops on sleeves, blue cap. Eight Kentucky Derby winners, at al. The red in the Calumet colors resembled the color on the can of Calumet Baking Powder. William Wright used the baking powder money to launch his racing stable. In 1940, Wright's son Warren hired Margaret "Maggie" Glass. For 42-plus years, Glass was Calumet's factotum, wearing spiffy outfits of Calumet colors that she sometimes made herself.

When Henryk de Kwiatkowski bought bankrupt Calumet in 1992, the colors had already been sold, for $12,000, to a Brazilian businessman. He used them only in Brazil, for one of the Wright heirs had the colors registered in New York. De Kwiatkowski, who died in 2003, raced in red polka dots; his daughter Arianne uses stars instead of polka dots.

4. King Ranch

Brown, white running "W" on back, white sleeves with brown hoop, brown and white cap. The silks came up big at Churchill Downs, where Assault won the Derby en route to the Triple Crown and where Middleground delivered a Derby encore.

The running "W" is the way the sprawling Texas ranch started branding its cattle in 1867. It has gone unexplained where the loopy letter came from. Some have said that it's not even a "W," but one of the diamondback rattlers that were found on the ranch. Others have said that it's a merged set of cattle's horns. Still others have suggested that it was a brand that cattle rustlers would find difficult to alter.

5. Charles S. Howard

Red, white triangle and "H," white sleeves, red and white cap. It was Marcela Howard, Charlie Howard's second wife, who designed the silks. One of the elements was the cattle brand that Howard had used at his Ridgewood Ranch in Willits, Calif.
A jockeys' baseball team, sponsored by Howard, wore replicas of the silks as uniforms. Instead of their own names, the jockeys embossed names of Howard's horses (Seabiscuit, Kayak II, and Noor were the most famous) on their backs.

In 2003, three sets of the silks worn by George Woolf when he rode Seabiscuit were auctioned off for $1,700, $1,100, and $1,000.

6. John A. Morris

Scarlet jacket and cap. Arguably, the first set of silks to be registered in the U.S. These date back to before the Civil War and were registered, according to The Jockey Club, in 1895. The Morris family owned Ruthless, the filly who won the first running of the Belmont, in 1867, and they also won another Belmont with Bowling Brook in 1898. John Morris, who was 95 when he died in 1985, and his wife, Edna, were familiar figures at New York tracks for decades. If Jean MacArthur, the widow of the general, wasn't with them, there was explaining to do. Morris, president of the old Jamaica track, gave out the trophy in the winner's circle when it closed in favor of a housing development in 1959.

7. Henry Clark III

Blue, with a white cap. Henry Clark III, who is carrying on with the family silks in Maryland, says he had an Aunt Maude − Maude Jennings − who challenged the Morris silks and said that the Clark colors were older. "She wouldn't give up," said Clark, known by most as Tim. "But going against The Jockey Club, we never had a chance of winning that one." The Clark silks also date to the 19th century. A Jennings colt, Dunboyne, won the 15th running of the Preakness in 1885. "I'm not saying (Aunt Maude) is wrong," said Lee Weil, a spokeswoman for The Jockey Club. "Record-keeping in the early days was inexact."

8. Meadow Stable

Blue and white blocks, blue sleeves, white stripes, blue cap. Riva Ridge, then Secretariat, then on the covers of Time, Newsweek, and Sports Illustrated. If you somehow missed the checkerboard silks, you noticed the dazzling blinkers. "The greatest sight in racing," said Penny Chenery, who raced Riva Ridge and Secretariat, "is seeing a horse, with your silks on, coming down the stretch on the lead." Second greatest? "Seeing a foal being born. That's God's gift to us." Washington and Lee University's colors are blue and white. A set of Secretariat's silks is still on display at the school, where Christopher Chenery, Penny's father and founder of Meadow Farm, studied engineering (Class of 1909).

9. Rokeby Stables

Dark gray; yellow braids, sleeves, and cap. By rights, there should be two sets. Paul Mellon used different silks when he raced his horses overseas. He won the Epsom Derby with Mill Reef and the Kentucky Derby with Sea Hero, one of only four owners to win both races. When Mellon, 91, died in 1999, he left $90 million and 130 valuable art pieces to Yale, his alma mater. A curator of art at the school once visited Mellon on Cape Cod. Mellon met him at the airport, driving a new gray Mercedes with yellow upholstery. "My racing colors, you know," Mellon said.

10. Claiborne Farm

Orange with an orange cap. That's The Jockey Club's designation, and in the game, they've been informally known for decades as Claiborne orange, although nobody believes it. They're really yellow. "School-bus yellow," a racing figure once said. Dell Hancock, the youngest of Bull Hancock's children, says it's easier just to call them gold. By whatever hue, the origin is murky. There's been the family story that Bull Hancock, who went to Princeton, modeled them after his school colors. Dell Hancock discounts the story.