Crown Yourself: The Secret Language of Race Day Hats
Photo by Grace Beahm Alford
The horses may be the main attraction at the Steeplechase of Charleston, but make no mistake: the hats steal the show. Whether perched delicately atop your crown or worn with playful panache, your choice of headwear whispers secrets about your style — and sometimes shouts them from the grandstands. So what exactly is your hat trying to tell the world?
Spring Style: Light, Bright & Breezy
The Wide Brim Straw Hat Works for: Everyone who loves classic elegance
A timeless choice that says you appreciate both style and practicality. Sun protection meets sophistication in this versatile option that flatters most face shapes, especially those with angular features. Perfect for creating that effortless garden party vibe while keeping cool under the Carolina sun.
The Fascinator Works for: Statement makers of all ages
Small but mighty, this delicate headpiece suggests you enjoy adding artistic flair to your ensemble. Fascinators work beautifully on smaller heads and complement softer facial features. They’re perfect for those who want elegance without overwhelming their outfit.
The Pillbox Hat Works for: Vintage enthusiasts
A nod to timeless sophistication that suggests you appreciate classic style. This structured hat works particularly well with oval and heart-shaped faces, sitting perfectly atop styled hair for that polished, put-together look.
The Equestrian-Style Cap Works for: Horse lovers of all ages
Think riding helmet meets baseball cap – these structured caps often feature horse-themed embroidery, barn names, or equestrian brands. They suggest you’re connected to the horse world beyond just race day. Great for all face shapes and perfect for those who want to show their genuine love of horses.
Fall Style: Rich, Bold & Sophisticated
The Felt Fedora Works for: Anyone wanting to add drama
This classic suggests you enjoy making an entrance. Fedoras work beautifully on longer faces and can be styled at different angles to compliment your features. Whether you’re channeling old Hollywood glamour or modern sophistication, this hat delivers impact.
The Bowler or Pork Pie Works for: Those who appreciate unique style
These distinctive shapes suggest you enjoy standing out from the crowd. Bowlers work well on most face shapes, while pork pies are particularly flattering on round faces. Both offer a playful nod to racing’s British heritage.
The Wool Beret Works for: Creative spirits
This soft, unstructured option suggests an artistic sensibility. Berets are incredibly versatile — they can be worn straight or at an angle and work with most face shapes. They’re especially lovely on those with strong jawlines or prominent cheekbones.
The Universal Crowd-Pleasers
The Boater Hat Works for: Everyone
This democratic choice works across ages, genders, and face shapes. The structured brim and crown show you appreciate classic style with a modern twist. It’s equally at home in the grandstand or the paddock.
The Baseball Cap (Elevated) Works for: Casual style lovers
Not your everyday trucker hat, the elevated cap has designer details, interesting textures, or vintage racing team logos. This relaxed choice suggests you value comfort without sacrificing style. The visor keeps the sun’s rays out for maximum viewing of the racetrack.
The Novelty Hat Works for: Fun-loving spirits of all ages
From miniature horses to champagne bottles, these whimsical creations suggest you don’t take yourself too seriously. Kids especially love these playful options — think tiny top hats, flower crowns, or caps with horse ears!
The Sun Visor Works for: Practical style enthusiasts
This sporty option suggests you’re here for the action and want to keep your view unobstructed. Visors work well for most face shapes and are perfect for those who want sun protection without hat hair.
Kids’ Corner: Pint-Sized Style
Mini Top Hats: Perfect for little ones who want to dress up like the grown-ups. These tiny versions of the classic suggest sophistication in a package that won’t overwhelm small faces.
Flower Crowns: A whimsical choice that suggests your little one has a free spirit. These work beautifully for spring racing and complement the natural beauty of the venue.
Racing Helmets (Toy Versions) For the kids who dream of becoming jockeys someday. These playful options suggest a love of the sport and adventure.
Face Shape Tips:
- Round faces: Try structured brims and higher crowns (fedoras, boaters)
- Square faces: Softer, curved brims work beautifully (wide-brim straws, berets)
- Heart-shaped faces: Medium brims that don’t overwhelm (pillbox, baseball caps)
- Oval faces: Lucky you—almost everything works!
- Long faces: Wide brims help balance proportions (boaters, wide-brim styles)
Lindsay Hibbard, lead milliner and long-time merchant of Steeplechase, offered some advice to attendees, suggesting, “Go big, go bold, and wear it with joy. That’s the real derby tradition: embracing fun, fashion, and fearlessness”.
Remember, the best hat is the one that makes you feel confident and comfortable. Your headwear choice ultimately says one thing above all: you understand that racing is as much about the pageantry and tradition as it is about the horses.
Show off your Race Day style! Tag @steeplechaseofcharleston or use #SteepleCHS for a chance to be featured on our social pages.