What to Wear to a Horse Race in the Main Line Region

From floral midi dresses to crisp white jeans, these local fashionistas dish on the best looks for equestrian events.

Look no further for what to wear to the races. Photos by Jim Graham

Get inspired by these creative takes on this year’s race-day looks (with some help from the Philadelphia Fashion Incubator).

Photos by Jim Graham
Shoot managed by Kim Douglas

red outfit
Jovan O’Connor pleated chiffon halter gown ($1,680).
white lace
Madelange Laroche fully lined lace jumpsuit (starting at $1,600); Tiffany Arey “Fashionably Late” white lace straw cocktail hat ($195); custom clutch by Conrad Booker.
patterned fashion outfit
Terese Sydonna magnolia floral print fan-sleeve dress ($350); Tiffany Arey “Have We Met?” straw teardrop hat with bow ($395); custom clutch by Conrad Booker.
bold fashion
Granate silk scarf with eco-friendly print (starting at $140) worn as a top; Tiffany Arey “Royal Regatta” saucer hat with sculpted feathers ($495); custom clutch by Conrad Booker.
patterned dress
Jovan O’Connor Valentina slinky dress ($185)
white fashion outfit
Granate Skyline embossed French knit on-shoulder dress with silk tassel details (custom).
white outfit
Granate one-shoulder raw silk dress (custom); Tiffany Arey “Well-Placed Sources” black and white graphic percher ($375); custom clutch by Conrad Booker.
fashion jumpsuit race day outfit
Granate custom corset top and slim-leg trouser with hand-painted silk organza hostess skirt ($695); Tiffany Arey “Come As You Are” straw biker cap with chain detail ($395).
fashion outfit
Granate Emerge trench coat (custom) with tendril skirt in embossed stretch metallic cotton ($695).
floral dress
Jovan O’Connor Misty Ballerina made-to-order dress ($1,170).
black and white outfit
Granate Clouds cotton and silk custom crop jacket and skirt suit with chiffon cloud insertions ($195).
orange fashion outfit race
Terese Sydonma marigold colorblock fan-sleeve dress ($265); Tiffany Arey “Groove” colorblock straw percher ($425).
pink skirt
Wear to Wall needlepoint top by Shelby Donnelly ($185); Samsara Sari Aanya knee-length skirt ($140); custom clutch by Conrad Booker.
blue skirt
Jovan O’Connor black stretch velvet crop top ($75) and circle skirt ($525); Tiffany Arey “Charmed, I’m Sure” black taffeta and ostrich feather hat ($590).
pink and blue fashion race day outfit
The Rani dress by La’ Agra ($923); Tiffany Arey “See and Be Seen” wide-brim hat with feather peonies ($425).
black dress
Granate tendril flutter knit dress ($398) and Bal Masque hand-painted silk organza overdress ($895).
white fashion
Granate embossed French knit one-shoulder dress with hand-painted silk organza corset belt overskirt (custom).
white fashion race day outfit
Madelange Laroche mini dress with sheer sleeves, applique bodice and rhinestone rope (starting at $1,500).
pink fashion race hat
Tiffany Arey “You Don’t Say!” beret ($395); LAGOS 18K Caviar gold bracelet ($6,900), earrings ($1,600) and ring ($1,750); LAGOS mother of pearl necklace ($3,750).
black outfit race day fashion
Tendrill Flutter knit dress with silk beaded cording straps ($398); Zephyr’ silk chiffon overskirt with silk beaded floral tassels and art print ($675); Tiffany Arey “Make an Entrance” straw/ textile percher with feathers ($425).

About The Shoot

Brian Cawley went to his first Point-to-Point at Winterthur at age 15 and never looked back. “After 35 years of working December holidays in retail, Point-to-Point is my holiday season—I haven’t missed any,” says Cawley, a visual merchandiser at Macy’s flagship Philadelphia store and a confirmed steeplechase aficionado.

In July 2021, Cawley collaborated with the Elissa Bloom, executive director of the Philadelphia Fashion Incubator, on its 10th anniversary. “We had so much fun on the project, we immediately started looking for other opportunities to partner,” says Cawley, who’s also on the Radnor Hunt race committee. “For over a decade, the Philadelphia Fashion Incubator has given [Macy’s] the opportunity to foster emerging designers. This season, we asked some of their most talented alumni to reimagine race patrons’ wardrobes. They embraced the project and have given us glamorous looks for this season and seasons to come.”

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The Philadelphia Fashion Incubator began 12 years ago as a one-year residency program for a handful of designers in the 800-square-foot workspace on the store’s fourth floor. “Our coursework is like an MBA for fashion entrepreneurs,” says Bloom. “Steeplechase is a perfect showcase opportunity.”

Originally drawing upon recent graduates from Drexel University, Moore College of Art & Design and the University of Delaware, the incubator has evolved to include second- and third-career designers. Each of them is focused on thoughtful solutions in fashion—gaps in the market. “The pandemic gave us a pause to consider how we’re investing our money,” says Bloom, “to be discerning about selecting timeless and long-lasting items—as these pieces are.”

Visit philadelphiafashion-incubator.com.

race day fashion blue outfit

Our Best of the Main Line Elimination Ballot is open through February 22!