Derby fashions

Styled by Melissa Gagliardi and Christine Fellingham | Photos by Kylene White | Hair by Shayna Shearer for Calvin Mitchell Salon | Makeup by Sloan Winters for Circe Beauty Bar

Our city’s 2-minute sporting event is more accurately a 24/7, week-long party that extends far beyond the gates of Churchill Downs. We took two models and a pile of pretty clotghes and millinery on a trip downtown to the history-drenched Black Jockeys Lounge on Fourth Street. Let our imaginary escapades and elevated ensembles inspire your own post-pandemic Derby celebration.

Night Moves

A ruched black dress looks polished from pre-track brunch until closing time. 

Derby fashions

The Hat Girls Fascinator, $650, at The Hat Girls boutique or Purse is Brahmin, $335, at Macy’s. Carolina Herrera dress, $1690, cuff, $250, and necklace, $350, all at Glasscock/Glasscock Too.

Fringe Benefits

A column of white will stand out in a dark lounge, or a sea of bright colors.

Derby fashions

The Hat Girls Fascinator, $430, at The Hat Girls boutique or Christian Siriano dress, $790, at Glasscock/Glasscock Too. Earrings, $14, bracelet, $20, bangles, $28 each, at Darling State of Mind.

Life of the Party

Sequins and paillettes are making an appearance for day and adding more flash and drama to dressing for this global occasion.

Derby fashions

The Hat Girls Fascinator, $460, at The Hat Girls boutique or Nicole Miller dress, $495, at Rodeo Drive. Necklace, $18, at Darling State of Mind.

Lounge Act

You don’t need a stage to attract a spotlight in chartreuse pleated silk with a plunging neckline.

Derby fashions

The Hat Girls fascinator, $430, at The Hat Girls boutique or Amur dress, $598, at Rodeo Drive.

Full Swing

Fourth Street is hopping, from The Mercury Ballroom to the Brown Hotel to Fourth Street Live – making the Black Jockeys Lounge a great first or last stop in a memorable Derby night out. For more info and reservations, go to

Derby fashions

Forme Fascinator, $550, at Forme or De Loreta top, $230, and bottom, $310, and BC Handbags, $125, at Glasscock/Glasscock Too.

Downtown Destination

In addition to its extensive bourbon selection, BJL is known for its inventive craft-cocktails. A must-have? The Willis Sims is a refreshing blend of bourbon, orange juice, maple syrup, orange bitters, vermouth and ginger beer named after the only Black jockey to win all three races of the Triple Crown. For their cocktail menu, go to

Derby fashions

Forme fascinator, $750, at Forme Millinery or Iris Setlakwe dress, $415, and bracelet, $25, at Glasscock/Glasscock Too. Coach purse from Macy’s.

Photo Finish

An embellished brim and slinky dress with side cut-outs make for a memorable photo opp.

Derby fashions

Forme hat, $750, at Forme Milliners or Significant Other dress, $240, at Glasscock/Glasscock Too. Bracelets, $18, at Darling State of Mind.


Models: Dominique Thompson and Maria Danyal for Heyman Talent

Photo assistant: William Kolb