Kentucky Derby - Holloway & Hare

Vintage-style illustration of a man in a classic light-colored suit and fedora hat, style guide for choosing a Kentucky Derby suit — Holloway & Hare.

Some Guidance for Choosing Your Kentucky Derby Suit

At the Kentucky Derby, some gentlemen opt for the versatility of a sport coat paired with trousers, while others choose the classic approach of a proper suit. If you’re considering the latter for Derby Day, this guide will help you get it right without overthinking.

Kentucky Derby

How the Mint Julep Became the Derby’s Signature Drink

The Mint Julep wasn’t created for the Kentucky Derby — but it might as well have been...In the early 1800s, juleps were taken medicinally — often in the morning. A little bourbon, a little mint, a little sugar...

Kentucky Derby

Embracing Heritage and Conservation at the Kentucky Derby

The Kentucky Derby represents a celebration of Southern tradition and sporting elegance. For generations, guests have gathered at Churchill Downs to celebrate not just horseracing, but a way of life that honors heritage, craftsmanship, and the natural splendor of the Bluegrass State.

Kentucky Derby

Kentucky Derby Rain Guide: What to Wear and Where to Watch

The Kentucky Derby doesn’t pause for rain—and neither should your style. Whether you're wondering what to wear to the Derby in the rain or looking for the best seats at Churchill Downs when it's raining, staying composed and dry is part of the tradition.

Kentucky Derby

Pocket Squares at the Kentucky Derby

A proper pocket square finishes a Derby ensemble. While seemingly simple, this detail requires careful consideration - particularly for an event where you'll be photographed throughout the day.

Kentucky Derby

Bow Ties vs Neckties at the Kentucky Derby

"A bow tie projects a certain confidence. It's not for everyone, but those who wear them seem to know they can carry it off." - G. Bruce Boyer

Back view of a man in a blue checked suit jacket and a woman in a bright pink hat, stylishly dressed for a British summer racing event.

Kentucky Derby

Kentucky Derby Suits and Jackets: The Smart Guide to Off-the-Rack

Here's a secret that some of the best-dressed men have known for generations: That perfectly fitted suit you admired? There's a good chance it started life on a rack. With the Kentucky Derby approaching, many men may be considering their first suit or sport coat purchase.

Kentucky Derby

The Last-Minute Derby Hat Guide: Finding Your Perfect Millinery With Just Weeks To Go

The clock is ticking on Derby preparations, but there's still time to secure that statement-making Kentucky Derby hat. Our comprehensive Kentucky Derby women's hat directory can help you find the perfect milliner, even with just a month to go.

Kentucky Derby

Men’s Shoes for the Kentucky Derby: The Perfect Finishing Touch

When it comes to dressing for the Kentucky Derby, the right shoes are just as important as the rest of your ensemble. The Derby is known for its bold fashion and celebratory atmosphere, which means your footwear should complement your look while keeping you comfortable throughout the day.

Kentucky Derby

Finding Your Perfect Kentucky Derby Hat: A Guide to Milliners

While department stores and boutiques offer Derby hats, working with a professional milliner provides distinct advantages. These artisans create custom pieces that consider not just your outfit, but your features, height, and how you'll wear your hair.

Stylish man in a navy suit, mint green shirt, coral tie, and Panama hat at Churchill Downs, with “A Gentleman’s Guide to Derby Dressing” text overlay.

Kentucky Derby

A Gentleman's Approach to Derby Dressing: One Month and Counting

With the Kentucky Derby now a mere month away, men still without appropriate attire might consider a thoughtful approach rather than a panicked one. The Derby, being both sporting event and social occasion, invites consideration of both tradition and individual expression.

Close-up of a man tying brown dress shoes, wearing bright pink and blue striped socks – men’s Derby Day style and sock guide.

Kentucky Derby

Men's Derby Day Style: The Sock Guide

When it comes to dressing for the Kentucky Derby, most gentlemen focus on their seersucker suits, colorful bow ties, and statement hats. However, the perfect pair of socks can be the subtle detail that elevates your entire Derby outfit.

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.

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.

Kentucky Derby

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.

Kentucky Derby

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.

Kentucky Derby

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...