The Hare - Holloway & Hare (Page 3)

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The Hare

Woman in a bright pink bespoke Derby hat watching horse racing from the grandstand – women’s hat style at the Kentucky Derby.

Bespoke vs. Off-the-Rack: Should You Invest in a Custom Derby Hat?

The Kentucky Derby isn't just America's most prestigious horse race—it's a cultural spectacle where fashion takes center stage alongside thoroughbreds. At Churchill Downs, your hat isn't merely an accessory; it's a statement piece that can define your entire Derby experience.

Tailor adjusting an orange tie on a man wearing a light blue linen jacket and pocket square – Derby Day style and linen jacket fit for the Kentucky Derby.

Is a Linen Jacket Appropriate for the Kentucky Derby?

The Kentucky Derby happens in May, when Louisville's weather can be wonderfully warm or surprisingly sultry. This often leads gentlemen to consider linen for their Derby attire.

Pair of men’s trousers with button-on suspenders draped over a hanger – classic Derby Day style and guide to wearing suspenders.

derby-accessories

The Ups and Downs of Derby Day Suspenders

As the first Saturday in May approaches and Louisville prepares for its grandest celebration, gentlemen across the country are piecing together their Derby day ensembles.

Gentlemen and ladies dressed in classic Kentucky Derby style, featuring a tailored navy suit, elegant fascinator, and champagne flutes at a race day event.

A GENTLEMAN'S GUIDE TO KENTUCKY DERBY FASHION: FIRST-TIMER'S EDITION

Just got invited to the Derby and starting from scratch with dress clothes? Don't worry - dressing for Derby Day isn't as complicated as it might seem. Here's what you need to know.

"Master milliner handcrafting a straw hat for Kentucky Derby millinery, showcasing traditional techniques and timeless hat-making artistry"

Kentucky Derby millinery

Behind the Brim: The Art and Legacy of Kentucky Derby Millinery

Today's Derby milliners often begin their journeys in unexpected ways. Some inherit family traditions stretching back generations, while others discover the craft after careers in fashion design or sculpture. What unites them is their dedication to preserving and evolving this distinctive art form.

Back view of a man in a blue pinstripe suit and straw boater hat with blue ribbon, dressed for the Kentucky Derby – classic men’s Derby hat style.

Men's Hats at the Kentucky Derby: A Guide to Classic Styles

While the spectacular creations worn by women tend to capture the headlines, men's hats have played their own significant role in Derby tradition. From the top hats of the Victorian era to today's refined selections...

Seersucker with button.

Why Seersucker Fits Into the Kentucky Derby Scene

When it comes to dressing for the Kentucky Derby, the event is as much about fashion as it is about horse racing. Among the many fabric choices seen at this iconic event, seersucker is a notable option.

Vintage photograph of elegantly dressed women in hats and fur at the Kentucky Derby grandstand – 1920s sporting style and Derby fashion history.

Derby Dress: A History of Sporting Style

The Kentucky Derby's dress traditions emerged from a blend of Southern sensibility and European racing customs. When the first Derby ran in 1875, gentlemen in the clubhouse followed the morning dress code common to prestigious European races

Historic photograph of Churchill Downs grandstand and Twin Spires in 1901 – early architecture of the iconic Kentucky Derby racecourse in Louisville.

Churchill Downs: An Architectural History

Churchill Downs began modestly. When the first Derby ran in 1875, the track consisted of a simple grandstand, a clubhouse, a porter's lodge, and a few wooden outbuildings.¹ The original grandstand held just 1,000 spectators, with tickets selling for $1.50.²