From Our Archive
This story was published before Summer 2021, when we launched our new digital experience.

Stylish Kentucky Derby Hats to Round Out Your Outfit for the Big Day

Let's be honest, your Kentucky Derby outfit isn't complete without a fascinator hat.

MOST READ STYLE
Peter Marino, the Architect King of Fifth Avenue

Design

Peter Marino, the Architect King of Fifth Avenue

Saving humanity’s live retail experience from the cold metaverse — one dazzling...

Behind the Wheel

Fashion

Behind the Wheel

How to put your best foot forward (and give your best “California Chic”) while...

Best Foot Forward

Fashion

Best Foot Forward

With their recent Proenza Schouler collaboration, Birkenstock steps fashionably...

If you make a purchase using the links included, we may earn commission.

To say that The Kentucky Derby is just another sporting event would be a gross understatement. In fact it is anything but ordinary. Every year, people flock to Louisville, Kentucky to witness “the most exciting two minutes in sports” and they bring with them the same flamboyant fashions and excitement that this race has been known for since 1875.

After a trip to Europe where he attended the Epsom Derby in England, the Kentucky Derby’s founder, Meriwether Lewis Clark, came back to the US determined to organize a similar event on this side of the Atlantic. And he wanted to recreate not just the horse racing part, but the formality and festive ambiance of it, too. He envisioned a high-class event where both men and women would come dressed up according to the latest fashions. And that’s pretty much how one of the most elegant sporting events in US history was born.

The main component of any race day outfit is, of course, the hat. So if you really want to stand out among your fellow spectators at this year’s derby, a creative headpiece is a must. It is the most important accessory you’ll wear that day so better make it count.

Here, we rounded up the ten most elegant hats and fascinators to wear at this year’s Kentucky Derby.

Vivien Sheriff Chorus Line Fascinator Hat

This elegant and eye-catching design by British milliner Vivien Sheriff consists of a woven disc in blue navy accessorized with a silk swirl and a touch of sparkling gold.

To buy: $907, harrods.com

Siggi Bow Sinamay Hat

Crafted from layers of sinamay, a fabric made from the stalks of the abaca tree, this stylish Siggi hat is accented by a feminine chiffon bow. This is a style that can also easily be re-worn at a wedding or another special event.

To buy: $465, harrods.com

Eugenia Kim Mirabel Textured Straw Sun Hat with Satin Bow

Opt for this beautiful Eugenia Kim style if you’d rather keep it simple and classy. This hat is made from natural straw and features a large downturn brim and a pretty black satin bow.

To buy: $495, neimanmarcus.com

Benoit Missolin Coco Hat

Add a vintage vibe to your ensemble with this boater hat reminiscent of the early 1920s. The classic design is complemented by a black ribbon and adorned with elegant pearl-like flowers and beads.

To buy: $382, modaoperandi.com

Camilla Rose Arrondi Headpiece

This eye-catching beret-inspired headpiece is handmade from natural straw. It features several straw loops lined with navy fabric.

To buy: $504, lovehats.com

Joanne Edwards Millinery Angelique Hat

Handcrafted in London by milliner Joanne Edwards, this stunning ivory and blue hat has an upturned brim design and is accessorized with a silk flower, rooster feathers, and arrowhead quills.

To buy: $520, joanneedwardsmillinery.com

Philip Treacy London OC Headpiece

This exquisite couture headpiece was created from an extended sinamay slice with a lace overlay, a crin, and a hand-blocked flower.

To buy: Price upon request, philiptreacy.co.uk

Bundle MacLaren Emilia Hat

This wide-brimmed sinamay headpiece has a feminine teardrop silhouette and is adorned with soft lilac arrow cut feathers.

To buy: $504, lovehats.com

Juliette Botterill Millinery Abaca Wrap Upturn Hat

An impeccably elegant design that will turn heads, the style has an upturn brim design and beautiful silk abaca wrap with a single ostrich quill.

To buy: $846, lovehats.com

Emily-Jean Millinery Elizabeth Hat

Irish milliner and jewelry designer Emily Jean O’Byrne has created this fun hat from ivory-hued sinamay. The piece is accented with flower buds and swirling quills, and is sure to make a memorable fashion statement.

To buy: $613, lovehats.com

Newsletter

Let’s Keep in Touch

Subscribe to our newsletter

You’re no longer on our newsletter list, but you can resubscribe anytime.