Kentucky Derby Style Guide

The Kentucky Derby is more than a prestigious horse race; it is an enduring celebration of style and sophistication. Known as ‘The Most Exciting Two Minutes in Sports’, the event has long been synonymous with impeccable fashion, where headwear is not just an accessory but a defining statement.

Unlike the understated refinement of Cheltenham or the formal traditions of Ascot, ‘The Run for the Roses’ embraces bold colours, elegant silhouettes, and a sense of individuality.

Whether you prefer timeless sophistication or a more contemporary edge, the right headpiece will elevate your ensemble with effortless grace. Follow our expert guidance and discover which hat to wear for the Kentucky Derby.

Which hat to wear for ‘Thurby’ on Thursday

A wide-brimmed hat is the quintessential Derby statement—chic, refined, and effortlessly polished. Whether you opt for clean, structured lines, soft vintage curves, or feathered accents for subtle movement, this style offers versatility and impact.

A monochrome palette exudes timeless elegance, while pastels and jewel tones add a fresh, modern touch. Pair with a tailored dress or a fluid silhouette for a look that is both sophisticated and effortless.

Which hat to wear for Kentucky Oaks on Friday

For a modern take on race-day millinery, a halo or structured headband provides an understated yet elegant alternative. Embellished with intricate embroidery, soft veiling, or sculptural bows, this style is refined yet effortless. Best paired with minimalist silhouettes, it allows the craftsmanship and detailing of the headpiece to take centre stage.

Choose a statement headpiece that exudes elegance and glamour for the Barnstable Brown Gala, the premier Friday night event of the Kentucky Derby.

Which hat to wear for the Kentucky Derby on Saturday

For a classic yet contemporary approach, a pillbox hat offers quiet refinement with a touch of vintage charm. Worn at an angle for a softer look or positioned further back for a more structured effect, it pairs seamlessly with tailored pieces, skirt suits, or elegant midi dresses.

A sculptural fascinator, featuring delicate beading and feathered detailing, brings a modern dimension to Derby dressing. Whether styled with a sleek sheath dress or an impeccably cut co-ord, this option balances sophistication with individuality.

Explore the Emily-London collection to find the perfect piece for your Derby Day look.