The down low on what to wear on top for the Kentucky Derby and beyond.

By Anne Bratskeir
Updated: May 02, 2019
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Mark Cuthbert/UK Press via Getty Images / Max Mumby/Indigo/Getty Images

When it comes to hats at the Kentucky Derby, there’s one very specific goal: Get noticed. There, ladies don some of the worlds most beautiful, eye-popping chapeaus topped by flowers, feathers, bows, and baubles, very often in luscious colors. Sometimes they’re modeled on the toppers worn by our royal sisters (yes, that would be Kate Middleton and Meghan Markle) who lean towards a less-is-more style fascinator (some are actually called hatinators – sort of the love child of the Derby hat and the fascinator) and are equally striking.

What’s the major difference? “A hat has a crown to it that that you put your head into and a brim that sticks out,” says Christine Moore of Christine A. Moore Millinery, who has been designing hats for 25 years and was named “featured milliner of the Kentucky Derby 144” last year. She’ll produce some 3,000 toppers for the hat-wearing set at horse events this year. “I call fascinators ‘a little confection for the head’ and it is technically a grouping of feathers on a comb, clip, or headband. It sits on the top of your head. Everything else, though people may call it a fascinator, is actually a cocktail hat. And there’s a term called the hatinator which frames the head like a hat but sits like a fascinator.”

Related: How Horses Travel to the Kentucky Derby

Moore credits Kate Middleton for the rise in popularity of the fascinator. “I’ve always liked them and worn them myself, but no one was interested in them. Then along came the royal wedding between Kate and Prince William in 2011 and that was a major boom for fascinators. The wedding was right before the Kentucky Derby and no one could keep them in stock. Since then they’ve been a staple in our collection.”

According to Moore, Kate’s style has a particular Kentucky Derby vibe. “It’s very feminine, a little elegant with a bit of whimsy to it. She looks very comfortable in hats and they seem to reflect her mood and personality and that’s how a good hat wearer should look. Kate’s a real fashion icon and everybody wants to be as beautiful as she is.”

Last year, leading up to the nuptials of Meagan Markle and Prince Harry (it happened to fall on the same day as the Preakness Stakes), Moore said she knew fascinators were going to come on strong. But she says, “Meaghan seems a little less comfortable in hats. It’s almost like somebody said to her ‘you have to wear this.’” (Maybe that’s the American roots and all.)  But, according to Moore, she’s managing well opting for clean lines but still elegant designs.

Moore says for herself, she’s more on team Markle. “I’m more of a streamlined type and I think there’s a real confidence in that ... it’s very chic.”

If you’re lucky enough to actually attend the Kentucky Derby, Moore says there are rules. “It’s all about the celebration of femininity though that could still be a tailored look – it’s the Southern Belle but not antebellum.” Medium to large brims are de rigueur for hat wearers and those wacky, over-the-top comical hats are, says Moore, “Less and less for the Kentucky Derby. You can add humor in a small, clever way and add a little gimmick like wearing the color of your horse’s silks. That’s like wearing face paint at a football game.” But, not any old hat will do. 

“Don’t wear a basic floppy hat or a street fedora. The Louisvillians will be very offended if you don’t come to the party properly dressed. After all this has been going on since 1875,” she said. As for color trends this racing season, Moore says, “Yellow is a big color along with light blue, and there’s lots of requests for red, which is surprising me.”

When picking your hat, whether you’re rooting for your favorite horse at a viewing party or heading to the Derby, “make sure that there’s some special defining characteristic about it,” says Moore. But most important is comfort. “If you futz with your hat and play with it all day, you’ll lose half your story. A lot of people wear their hat for the whole day so make sure your hat fits well.”  Overall, she says, “People don’t realize the power of a hat. You want to walk into whatever event it is and have people say, “You look amazing. You want to live it like a Louisvillian. It should be sheer joy.”

Whittall & Shon Derby Hat

Courtesy of JCPenney

Feminine touches such as feathers, flowers, and a handful of sequins give this pastel pink derby topper great appeal.

To buy: jcpenney.com, $66

Whittall & Shon Special Occasion Hat

Courtesy of JCPenney

Statement making chapeau is bedazzled with rows of gold ribbon and sparkly purple crystals along with sculptural fabric florals.

To buy: jcpenney.com, $108

ModCloth Sassy Statement Fascinator

Courtesy of ModCloth

Netting, feathers and flowers, oh my! This chic little ivory fascinator stays in place via headband.

To buy: modcloth.com, $35

ModCloth Sweetest Spread Fascinator

Courtesy of ModCloth

Go the Meghan Markle route with this streamlined black fascinator with a dotted veil.

To buy: modcloth.com, $19 

Red Rose Sinamay Fascinator

Courtesy of Amy Jo Original Hats/Etsy

Red is this racing season’s standout color so consider this fascinator featuring a dozen handmade red roses and graphic green bow by Amy Jo Original Hats.

To buy: etsy.com, $325

Yellow Big Brim Kentucky Derby Hat

Courtesy of Elmira Exclusive/Etsy

Make a statement in this oversized Kentucky Derby hat in one of the season’s most popular colors. This one by Elmira Exclusive – in crinoline – features flowers and bows.

To buy: etsy.com, $189

Outtop Party Hat

Courtesy of Outtop

Add a bit of whimsy to your derby day look with this feathered mesh number that attaches with a clip.

To buy: walmart.com, $13

Meihuida Derby Hat

Courtesy of Walmart

Another of the racing season’s hit colors – pale blue, this foldable wide brim cap features a decorative flower.

To buy: walmart.com, $8

Hirgin Feather Mesh Fascinators Hat

Courtesy of Walmart

This sweet feathery topper includes a headband with a forked clip.

To buy: walmart.com, $8

August Hats Flower Netting Fascinator

Courtesy of Macy's

This umbrella-shaped fascinator features a major blossom in the center with fluttery feathers attached.

To buy: macys.com, $68

August Hats Gathered Tulle Wide Brim Dressy Hat

Courtesy of Macy's

This wide brimmed classic boasts a swath of tulle for added interest.

To buy: macys.com, $88

Marc Jacobs x Stephen Jones Millinery Boater Hat with Veil

Courtesy of Marc Jacobs

Lacquered metallic straw meets delicate French veiling and netting for a high fashion look.

To buy: marcjacobs.com, $350

Giovannio Veil Fascinator

Courtesy of Lord and Taylor

Add a dash of English proper with this spare but sculptural veil fascinator.

To buy: lordandtaylor.com, $74

Women's Scala Sinamay Derby Floppy Hat

Courtesy of Kohl's

A big, floppy taffeta brim in royal blue has a bow focal point and a bit of feather.

To buy: kohls.com, $63

Christine A. Moore Millinery Kate Middleton-inspired Topper

David Dobson Photography

Evocative of Kate Middleton’s penchant for feminine yet whimsical toppers, this hatinator designed by famed NYC milliner Christine A. Moore includes a silk ribbon and French net — a perfect Derby look.

To buy: camhats.com, $440

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