Keeneland

Photos: See how Keeneland fashion has changed over the years

By Brian Simms

The Keeneland Fall Meet is back with lots of new amenities for race fans to explore.

For the 2025 Fall Meet, which runs Oct. 3-25, the Lexington racetrack will debut a new Paddock Building, East Gate entrance, and more after one of the biggest construction projects in Keeneland history.

But one thing that hasn’t changed in the 89 years of thoroughbred racing at the track is the fashionable looks.

Each Spring and Fall Meet, men women and children wear their Sunday best no matter what section of the track they are seated in — or standing in if you simply go to tailgate at the Hill or wander the historic grounds.

Race-day outfits in the 1940s and ‘50s for the women included high heels and small hats (the term “fascinators” was not invented until the ‘60s) and fur coats if there was a chill in the air.

Mrs. Frank Atkins, Mrs. P.J. Sawyer, Mrs. Lewis Bush and Mrs. L.Q. Bickett were guests in Mr. and Mrs. Barckley Storey's box at during the 1947 Keeneland Spring Meet. The photo was published in the April 21, 1947, Lexington Leader, alongside other social news items. The 1947 spring meet lasted 11 days.
Mrs. Frank Atkins, Mrs. P.J. Sawyer, Mrs. Lewis Bush and Mrs. L.Q. Bickett were guests in Mr. and Mrs. Barckley Storey's box at during the 1947 Keeneland Spring Meet. The photo was published in the April 21, 1947, Lexington Leader, alongside other social news items. The 1947 spring meet lasted 11 days. Herald-Leader archive photo
Patrons enjoying the clubhouse lawn at Keeneland Race Course in October 1954 included, seated from left to right, Mrs. William Carl, Mrs. W.T. Bishop, Mrs. Charles Rhodes, Mrs. Harry Scott Jr. and Mrs. Richard Arnspiger. Behind them were Mrs. Warren Wright Jr. and Mrs. Jack Wilkinson.
Patrons enjoying the clubhouse lawn at Keeneland Race Course in October 1954 included, seated from left to right, Mrs. William Carl, Mrs. W.T. Bishop, Mrs. Charles Rhodes, Mrs. Harry Scott Jr. and Mrs. Richard Arnspiger. Behind them were Mrs. Warren Wright Jr. and Mrs. Jack Wilkinson. Herald-Leader Archive Photo

But the fashion took a big step forward in the years to come, as displayed in a “Social, Personal and Fashion News” spread in the Sunday Herald-Leader published on Oct. 19, 1971.

The pictures and captions showed women’s fashion for the Fall Meet from many popular Lexington stores of the time, including Stewart’s, McAlpin’s and Wolf Wile’s, which was downtown Lexington’s last department store, closing in 1992.

Fitting with the era, tweed was a fashionable and popular choice for many of the outfits on display.

Mrs. William Lockridge, left, prepares for the cooler weather in a double-breasted slightly-fitted man-made fur coat. These fabrics are water-repellent and will not shed. Flap pockets detail this coat from Town and Country. Mrs. Hampton Adams Jr. brightens the Keeneland paddock in a yellow wool jersey with wide wine suede belt with large silver buckle by Joan Leslie from Loom and Needle. Dave Burgan is aboard Jenny Song, owned by Mrs. Blanche Kercheval.
Mrs. William Lockridge, left, prepares for the cooler weather in a double-breasted slightly-fitted man-made fur coat. These fabrics are water-repellent and will not shed. Flap pockets detail this coat from Town and Country. Mrs. Hampton Adams Jr. brightens the Keeneland paddock in a yellow wool jersey with wide wine suede belt with large silver buckle by Joan Leslie from Loom and Needle. Dave Burgan is aboard Jenny Song, owned by Mrs. Blanche Kercheval. Frank Anderson Herald-Leader staff file photo
Mrs. Hal Price Headley Jr., left, wears a black and brown slate combination semi-fitted tweed coat with notched lapels and brown suede belts by John Clark of Dublin from Wolf Wile’s. Her hat, with wide brim, is of dark brown Italian velour by Mr. D. Her brown calf bag, with gold chain handle is by Korea. For a day at the races, Miss Mason Winn selected a dress with brown tweed skirt and gold jersey top with flattering roll collar. The costume is completed with a brown suede jacket with pocket detail by Helen Matthew. The boots are by Rosetta, all from Hymson’s. With the ladies is jockey Larry Rowe holding Lady Slipper from Lazy F. Ranch.
Mrs. Hal Price Headley Jr., left, wears a black and brown slate combination semi-fitted tweed coat with notched lapels and brown suede belts by John Clark of Dublin from Wolf Wile’s. Her hat, with wide brim, is of dark brown Italian velour by Mr. D. Her brown calf bag, with gold chain handle is by Korea. For a day at the races, Miss Mason Winn selected a dress with brown tweed skirt and gold jersey top with flattering roll collar. The costume is completed with a brown suede jacket with pocket detail by Helen Matthew. The boots are by Rosetta, all from Hymson’s. With the ladies is jockey Larry Rowe holding Lady Slipper from Lazy F. Ranch. Frank Anderson Herald-Leader staff file photo
Mrs. John H. Hardwick, left, enters the track wearing a brown Donegal tweed dress and jacket by Dominic Pompollo. The dress features a brown jersey top with high collar from Ebro’s. Her hat is of brown velour with the Chanel profile. Mrs. Barrett H. Morris, center, selects a double-breasted midi coat in deep green with brass button detail by Peabody House from Four Season. Mrs. David Parrish is seen in a Jaeger skirt and single breasted wide-lapel blazer, both camel. With it she wears a gray cashmere turtleneck sweater by Pringle of Scotland from Meyers.
Mrs. John H. Hardwick, left, enters the track wearing a brown Donegal tweed dress and jacket by Dominic Pompollo. The dress features a brown jersey top with high collar from Ebro’s. Her hat is of brown velour with the Chanel profile. Mrs. Barrett H. Morris, center, selects a double-breasted midi coat in deep green with brass button detail by Peabody House from Four Season. Mrs. David Parrish is seen in a Jaeger skirt and single breasted wide-lapel blazer, both camel. With it she wears a gray cashmere turtleneck sweater by Pringle of Scotland from Meyers. Frank Anderson Herald-Leader staff file photo
Mrs. Joseph A. Owens II, left, wears a blue and camel acrylic costume perfect for the changeable days of fall in the Blue Grass. The sleeveless top is blue and the skirt is coordinated with the pocket accent on the coat. With it she wears a camel felt hat with cutout detail, pointing to the return this fall of the real hat. Her costume is from Meyers. Mrs. Charles Nuckols III, selects a double-breasted plaid blazer with charcoal flannel skirt and matching knit top from McAlpins’s. The costume was designed by Kasper for Joan Leslie.
Mrs. Joseph A. Owens II, left, wears a blue and camel acrylic costume perfect for the changeable days of fall in the Blue Grass. The sleeveless top is blue and the skirt is coordinated with the pocket accent on the coat. With it she wears a camel felt hat with cutout detail, pointing to the return this fall of the real hat. Her costume is from Meyers. Mrs. Charles Nuckols III, selects a double-breasted plaid blazer with charcoal flannel skirt and matching knit top from McAlpins’s. The costume was designed by Kasper for Joan Leslie. Frank Anderson Herald-Leader staff file photo
Mrs. John Gaines, left, wears a classic David suit executed in Scottish purple and green tweed with matching purple blouse from Embry’s. Her Tyrolean brim hat is in a wild grape shade. Miss Clay Hancock’s choice for cooler days is a burnt orange fake fur with black trim and leather closings by Natalie Green from Stewarts.
Mrs. John Gaines, left, wears a classic David suit executed in Scottish purple and green tweed with matching purple blouse from Embry’s. Her Tyrolean brim hat is in a wild grape shade. Miss Clay Hancock’s choice for cooler days is a burnt orange fake fur with black trim and leather closings by Natalie Green from Stewarts. Frank Anderson Herald-Leader staff file photo

This story was originally published October 3, 2025 at 11:06 AM.

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