Fall Hat Trends 2019

BreedersCup Hat Tips!

Churchill to Host Breeder’s Cup Again

Once again, for the 8th time, in fact, Kentucky’s Churchill Downs will host the Breeders’ Cup. The 28th running of the Breeders’ Cup will take place at our state’s historic racetrack November 4 and 5th and we’re featuring Breeders’ Cup Hats.

Since the inaugural running at Hollywood Park 27 years ago, the Breeders’ Cup has established itself as the season-ending championship of thoroughbred racing. Through the years, the Breeders’ Cup has grown from a 7-race, $10 million day, to a 15- race, $26 million extravaganza, held over two days, and encompassing almost every division of the sport. The purses for the Championship races are funded by worldwide nomination from the industry’s thoroughbred breeders. In 2011, horses are able to earn automatic starting positions into Championships races through the Breeders’ Cup Challenge, a series of 68 stakes races held worldwide.

“I am thrilled that Kentucky’s iconic Churchill Downs, home of the legendary Kentucky Derby, has been selected to host the 2011 Breeders’ Cup World Championships,” Governor Steve Beshear.

What to wear to the Breeders’ Cup? While hats are not de rigueur as at Royal Ascot, or even traditional as at the Kentucky Derby, we design a number of hats every year for owners who anticipate a spot in the winners circle and for racing fans who simply enjoy cutting a smart figure in the stands. If you plan to attend the event there’s a very good reason to choose your head wear carefully; On Friday, November 4, Louisville newspaper,The Voice Tribune will be sponsoring “Fascinator and Fedora” a hat competition in which one fashionable fan will walk away with $5,000 for the best Fascinator and another will win $5,000 for the best Fedora. For more information follow this link: Fascinator and Fedora

Since the royal wedding we’ve seen a trend toward the saucer hat made popular by the Duchess of Cambridge Catherine Middleton. The smaller hats and fascinators work well with all types of ensembles — even pants suits. One of our most popular saucer hats was named for Zenyatta, the filly that has become practically the symbol of The Breeders Cup.

Below are some new additions to the line designed with this event in mind.

Love Wisely
Ruby Tuesday
I wouldn’t presume to predict Kentucky weather in early November, however, historically, there have been some warm quite sunny days. As wise women protect themselves from too much uv damage, a wide brimmed hat may well be a good investment in the day. For this reason, Polly always adds a few new hats which provide full coverage, yet are designed with fall fashions and palettes in mind. We call them “Transitional Straws”. In fact, our line of transitional Straws are traditionally named after former Breeders Cup winners –evocative names like Ginger Punch, Dance Smartly to name a couple. To view and read more about these versatile and elegant designs follow this link to an earlier post entitled Breeders Cup Heads Up.
Skip Away

Whether you choose the chic fascinator or saucer hat and a shot at the prize money or go for the mystery of a more traditional wide brimmed design, we welcome you to Kentucky and promise you that the Breeders Cup will be a day unbridled excitement.

by Jan masters Yon

Holiday Fascinator: a spoonful of fun

Mademoiselle Colette

Thrilling things often come in small packages – that has never been more true than this autumn at Polly Singer Couture Hats and Veils. Just in time for the holiday party season, we’re unveiling a collection of hats so petite and precious they should be measured in carats.

The seven bewitching new fascinators run the gamut from unabashedly romantic to sophisicated and mysterious. The common characteristic is that each little headpiece packs a head turning punch. In some of the designs, Moulin Rouge and Domino for instance, much of the dazzle is created by the exhuberant interplay of long feathers and lush silk flowers.

Moulin Rouge
With several of the designs, veiling sets the mood —and the moods do vary. In the case of Frappé an ivory bird cage veil whispers innocently of romance. Frappé is popular with brides as a less formal wedding veil, or as a reception headpiece. It also works fabulously well with winter white wool. On quite the opposite end of the spectrum is Kir Royal. A mysterious dark veil, shot with white velvet floats beneath rich black trims and violet velvet. Tutti Frutti owes it’s whimsical appeal to an amusing chin length veil across which candy colored dots play giving the illusion of a constant shower of confetti.

Kir Royale
Tutti Frutti

All of these designs play well with a little black dress. Moulin Rouge and Grenadine Fizz take advantage of crimson’s affinity for black and white. Moulin Rouge brings the glamor of a casino to basic black. More playful, yet every bit as eye catching is Grenadine Fizz with its wisp of a veil and sassy scarlet and white trim.

Grenadine Fizz

Crème de Menthe is a study in movement and vivid color. Among the dancing black feathers iridescent peacock spires glimmer, working their timeless magic.

Creme de Menthe

These charming little hats range in price from $190. to $250. and are brilliant at breathing new life into last year’s party dress. The right fascinator can transform an otherwise conservative ensemble into a stunning holiday look. This Thanksgiving, I refuse to go over the river and through the woods dressed like a pilgrim. This sweet whimsey in Cocoa guarantees that I won’t be upstaged by a turkey. Whether you want to be the girl in the limelight or the mysterious siren of the shadows I encourage you to consider a fascinator. In fact, you might as well take two —remember, they’re small.

photo by Elaine Shay
By Jan Masters Yon

Note: We enjoy hearing from readers and invite your comments. My email address is jan@hatsandveils.net. Polly may be reached at polly@hatsandveils.net. We both look forward to your input.

Christina’s Fascinator for Del Mar

Christina's Del Mar Fascinator
As always, I did many hats for Del Mar Racetrack’s Opening Day. This past Wednesday, ladies were out and about in their hats for the annual hat contest.

This is the 3rd year that I have designed a hat or fascinator for TVG’s Christina Olivares. This year, she chose a fascinator to complment her dress. As you can see, the fascinator ties in the orange and light blue from the dress. Christina’s own hair color ties in the with brown.

Christina's Dress
When I saw the dress, I immediately thought that the orange and blue feathers would stand out nicely against her hair and go with her coloring. It’s nice when design projects come together so easily. As always, Christina is a delight to work with and I feel lucky to have met her. She’s an intelligent, hard working lady who grew up around horses (her dad was a jockey).

By: Polly Singer

Royal Ascot: Win by a Head


Everyone has a head, so everyone has a possibility to wear a hat. People feel better for wearing them.
Philip Treacy

The Royal Ascot Race Meet, Ladies Day in particular, is one of the high holy days of millinery design. Beautiful, luscious, sometimes daring hats repose on every head. In accordance with the Dress and Etiquette Code requirement for entrance into the royal enclosure, strapless dresses, halter tops, bare midriffs, spray-on tans and any display of underwear is strictly frowned upon, however hats for ladies and top hats for gentlemen are compulsory. Yet another reason to be an anglophile.

In my opinion, Ascot 2008 saw the British Royal Family better turned out than ever before. According to United Press International, bookmakers in England reported a high number of bets were placed predicting that Queen Elizabeth II would break with tradition and attend opening day sporting a fascinator, that is, a small lavishly trimmed hat worn at a jaunty angle.


However, the Queen arrived wearing a pastel blue Phillip Somerville squarely set, medium brimmed hat to accessorize her Steward Previn dress and coat. On Thursday, Ladies Day, Her Royal Highness was both elegant and chic in a black and ivory print dress/coat ensemble topped with an asymmetric brimmed hat in ivory with a spray of black silk leaves. All three pieces were designed by Rachel Trevor-Morgan.


The entrance of Queen Elizabeth may have left a raft of disappointed bettors in its wake but the younger members of the royal family overwhelmingly chose the fascinator as a race day favorite.

Zara Phillips, daughter of Princess Anne appeared in a gravity defying monochromatic saucer hat in cream colored straw trimmed with a brace of large cream colored roses.


HRH Princess Beatrice wore a smart, small white fascinator trimmed in black, her sister HRH Princess Eugenie sported a small blue cap heaped with blue silk roses and periwinkle blue cut coque feathers. Both hats were worn low on the forehead and off-center. Thursday, Ladies Day, both granddaughters of the Queen followed the trend of neutral colors and asymmetry with small cream colored hats worn at dramatic angles.


I’m pleased to tell you that All You Need is Love Hats and Veils was represented at Ascot – in the Royal Enclosure, no less. Recently, Polly had the enviable task of creating a hat for a young woman’s first visit to Ascot. The resulting design was, as you might guess, neutral in color, designed to be worn off kilter, trimmed with a cascade of stripped coque feathers tucked under a smartly angled brim. A prototype of the hat and Nicole Miller dress, courtesy of Lexington’s Bella Rose which inspired it is shown here modeled by Isabel Abbott Yon, Junior Member of the Lexington Ballet Company.


One needn’t attend The Royal Ascot Race Meet to learn from it. More pictures of racegoers can be seen by visiting the following links.



To recap, so to speak, millinery trend spotters, be alert to fascinators, monochromatic, neutral palettes and shallow crowned saucer hats trim both over and under the brim – all worn on the diagonal. Inspired by Ascot, Polly will be posting some new designs along these lines. I encourage you to watch for them on the website and, as always, will be interested to hear your opinions.

By Jan Masters Yon