Holloway & Hare (Page 2)

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Holloway & Hare

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Illustration of four stylish women’s hats in various colours, promoting a guide to finding your perfect milliner for race day and special occasions.

Finding Your Milliner: A Guide to Hats, Heritage, and the Hunt for the Right Fit

Every June, the lawns of Royal Ascot bloom not only with roses but with feathers, veils, sculptural twists, and a riot of colour balanced delicately upon the heads of women who know—this is no ordinary hat moment. It is a stage, a tradition, and for some, a minor performance.

Woman in a cream dress wearing a bright pink sculpted fascinator hat at Royal Ascot, showcasing classic race day style.

Hats at Royal Ascot: Notes on Form, Etiquette, and Makers

For many women attending Royal Ascot, the question of what to wear begins—and often ends—with the hat. It is the most visible expression of dress at the event, shaped not only by tradition but also by official rules.

Man in classic morning dress with top hat, light grey waistcoat, and pale blue tie – Royal Ascot style for the Royal Enclosure.

Royal Ascot Morning Dress: A Guide for the Royal Enclosure

The Royal Ascot Royal Enclosure is by invitation only. Attendance requires either nomination from an existing member or approval via formal application. It is, by design, a place apart—more restrained than the grandstand, and with a dress code that is closely observed.

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.

Man in a classic black silk top hat and morning dress, suitable for the Royal Enclosure at Royal Ascot.

A Note on Top Hats at Royal Ascot

The Royal Enclosure has rules. Some are printed, others simply understood. Among them: a proper top hat. It isn’t optional, and it isn’t a nod to nostalgia. It’s part of the dress code, same as the morning coat, waistcoat, and tie.

Man in morning dress and woman in a white lace dress and statement hat at the Royal Enclosure, Royal Ascot.

The Royal Enclosure at Royal Ascot

The Royal Enclosure is the most traditional and formal area of Royal Ascot. Accessible by invitation or membership only, it reflects a long-standing association with the royal family and the ceremonial side of British sporting life.

Classic mint julep cocktail with bourbon, ice, and fresh mint garnish – signature drink of the 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...

Historic black and white photo of horse racing at Churchill Downs, with packed grandstands and the iconic Twin Spires during the 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.

Horses racing on a muddy Churchill Downs track in the rain, with crowds watching from the stands during the 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.

Thurby horse race at Churchill Downs with jockeys and scoreboard – a popular day for locals during Kentucky Derby week.

Thurby: The Smart Day to See the Track

If you’re in Louisville today and not at Churchill Downs, you’re missing the best opportunity of the weekend to actually experience the track.

Old Forester Distilling Co. sign and Bourbon District banner on historic Whiskey Row in downtown Louisville, Kentucky – birthplace of bourbon.

A Good Use of an Afternoon: Louisville Distilleries to Visit During Derby Week

If you're visiting for the Kentucky Derby and find yourself with a few unscheduled hours, skip the lobby and explore something Louisville does exceptionally well: bourbon.

Group of sheep grazing in a British pasture with bare trees and rolling hills – tracing the journey of wool from farm to hanger.

Ad Fontes: Tracing the Journey of Wool from Hill to Hanger

The phrase ad fontes—"to the sources"—was once the call of scholars and reformers, urging a return to origins, to clarity, to the unfiltered integrity of things. Today, it feels just as relevant in the world of cloth, craft, and culture.

Silk, linen, and cotton pocket squares in vibrant spring colours and patterns, including paisley, checks, and polka dots, styled for Kentucky Derby race‑day elegance.

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.

Floral print necktie and embroidered navy bow tie displayed on a green background – men’s tie styles for the 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 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.

Smiling woman in a floral dress and wide-brimmed Derby hat with yellow roses and pink ribbon, attending the 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.

Brown and white men’s spectator shoes with brogue detailing – classic Kentucky Derby footwear style.

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, vintage photo, 1930s fashion, boater hat, Derby tradition, American style

Dressing for Derby: The American Tradition

The Kentucky Derby stands alone in American sporting life - a rare occasion where getting dressed is as much part of the tradition as the race itself. Following its historic 150th running, the Derby continues to showcase the best of American sporting style.¹

Garland of red roses draped over the 149th Kentucky Derby sign at Churchill Downs, with grandstand and Twin Spires in the background – Derby traditions.

Derby Traditions: Roses, Juleps, and Southern Style

The Kentucky Derby's traditions weren't planned by committee - they evolved naturally, often by happy accident. Take the mint julep, which wasn't even the original Derby drink.

Kentucky Derby women’s hats at a luxury milliner’s shop featuring elegant wide-brimmed hats, fascinators, and designer headpieces for race-day style

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.

19th-century illustration of Peytona and Fashion’s Great Match horse race at Union Course, Long Island, with large crowds and carriages – early American horse racing history.

Origins of the Kentucky Derby

The Kentucky Derby began with Meriwether Lewis Clark Jr.'s transformative European travels in 1872.¹ Witnessing both the Epsom Derby and the Grand Prix de Paris, Clark returned to Louisville with a vision for creating an American equivalent to these prestigious races.²

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.

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.

Illustration of a man in a blue suit, bow tie, and boater hat with the text “Getting Ready for the Kentucky Derby – Style Advice for Gentlemen” and a horse graphic.

Derby Men's Clothing Guide: 2025 Style Guide for Churchill Downs

The Kentucky Derby demands more than mere fashion—it requires an understanding of sporting tradition, cultural heritage, and the delicate balance between classic style and contemporary interpretation.

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

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.