How to Choose a Hat for Your Face Shape

Intern Shelby Parrott here! Shopping can feel intimidating, especially when shopping online.”Will this look good on me? Will it flatter me and my face shape? What even IS my face shape?” Well, no worries! We got you, girl! While, obviously, you can wear whatever hat style you want, sometimes when you’re shopping online for a hat for the first time, it can be nice to have some directions before you go off driving on your own. So, here are ways to determine your face shape and what hats will suit you the best before you hit the “add to my cart” button on a Polly Singer Couture Hat! 😉 

The best way to figure out your face shape it to either take a photo of your face or look in the mirror and with your finger outline the shape of your face. To get the full look it is best to tie your hair back to get your full face in view. You could also whip out the measuring tape if you feel like it, but it is best to just examine your face and facial features. Determining your forehead, cheeks, jaw, and face lengths are the keys to figuring out facial shape. 

And what better way to learn about what hats to wear than from the best hat wearers out there? The Royals!

Kate Middleton | POPSUGAR Celebrity   Billie Light Tan Fedora With Bridal Bits
Kate Middleton: Oval Face Shape
Lucky you, oval face shapes work with pretty much anything! It is best to not go with anything too round or narrow to the face because sometimes that can make the face look smaller and rounder. Our best suggestion would be a fedora. It’s the perfect in between like the oval face shape! It’s not too wide or too close to the face, not to mention a classic that you can wear season after season. Some things just never go out of style!   Virginia black cloche
Meghan Markle: Heart Face Shape
The heart face shape usually consists of a wider forehead and a pointy chin making the perfect heart-like shape! Heart shape faces also go with many different styles but it is best to stay away from wider brims and floppier hats as they can make the forehead look larger and not flatter the face shape as much. The best would be a hat that is closer to the face or a medium to smaller brim to perfect fit your face. 
Our suggestion would be the Virginia Black Cloche Hat.  Perfect for this face shape plus not to mention a lovely vintage inspired look. 
Princess Beatrice celebrates 27th birthday: 10 facts | HELLO!




Sally Honey Brown Profile Wool Hat

Princess Beatrice: Round Face Shape

With round face shapes, it is best to stick with hats that are not close to the face. If the hat sits too close to the forehead or the rest of your face it can just emphasis the roundness. It is best to go with a wider brim and, even better, something that is upturned from the face to give your face height. Or wear your hat slanted back for the same look.

Are suggestion would be the Sally Tan Upturned Hat. It’s wide and upturned brim is perfect for rounder face shapes! Plus it’s a great Fall essential for your wardrobe! 


Diana, Princess of Wales - Wikipedia   Isabelle Huge Panama Ladies Sun Hat
Princess Diana: Square Face Shape
Square face shapes usually consist of a strong jawline, great high cheekbones and a longer face. With square face shapes, go with a wide floppy style hat. This way it softens the look and contrast greatly with the square jaw line. 
We suggest our Isabelle Oversized Sun Hat. Perfect with its wide and floppy brim. Plus not to mention making a fun fashion statement! 

Don’t forget though, wear whatever makes YOU feel good! These are just some guidelines you can follow if you’re feeling unsure. But, of course, how you feel is the most important. 

Happy Shopping! 

5 Iconic Hats from Films

Costumes make a film and, with the right costume designer, can convey so much about a character to the audience before they even utter a word. It’s not just the clothes on their back that make it either, it all comes from the accessories too, hats included! Every little detail of a character’s wardrobe can tell us so much about them and who they are. Here are 5 of the most iconic hats from movie history! 

One of the most fashionable characters in film history has got to be Holly Golightly from Breakfast at Tiffany’s. The image of Audrey Hepburn standing outside of Tiffany’s in a long black dress decked out in pearls is one of the most iconic scenes in film history and is the definition of the perfect “little black dress”. But nothing beats the wide brimmed black hat with a cream colored silk bow.

The costumes for the film were designed by French fashion designer Hubert de Givenchy and Audrey looks beautiful in every one. Her elegant wardrobe throughout the film shows how Holly wants to escape her pervious county girl life for the upscale New York life. 

Another one of film’s most fashionable characters hands down has got to be Scarlett O’Hara. The film spans 12 years from 1861 to 1873 and sees Scarlett’s life go through many changes. From privileged young Southern belle, to struggling to feed herself and her family, to fabulously wealthy business woman. Her costumes through the film highlight her struggle and changes in life. From the fluffy white dress in beginning showing her childhood and innocence to her calico dress that she wears through a good course of the film because she has no money, and then the beautiful gowns she wears when she has money from the lumber mill and marriage to rich Rhett Butler. With many of her outfits she wears hats or head pieces that perfectly match with her dresses. 

There are so many to choose from but I have to go with the hat she wears with the iconic green curtain dress. While not necessarily the most outrages of her dresses, it is certainly the most memorable. It was even parodied by comedian Carol Burnett in the 90s on her show. She wears the dress to meet Rhett in jail in Atlanta to get money to save Tara showing how dedicated she is to saving her beloved Tara. 

Does Audrey Hepburn make two appearances on this list? Yes, yes she does. Because she is just that fabulous. But I mean look at this hat! How could it not make the list? The insane hat is from the film My Fair Lady. The movie came out in 1964 and had a budget of 17 million. It was the most expensive film made in the US at the time. Costume designer Cecil Beaton designed more than 1,000 costumes for the film and won the Academy Award for Costume Design. 

This hat is worn by Eliza when she attends the Royal Ascot after her makeover to become a high class society girl. The hat, along with the dress, were auctioned off for $3.7 million dollars! 

Time to show the fashionable men some love! While this is not the most crazy or interesting hat by any means, it certainly has left its mark. Once the first Indiana Jones movie came out many men wanted to sport this iconic brown fedora to be like star Harrison Ford. Indy wears a simple white button down with brown slacks, leather jacket and the hat just makes the look forever memorable. People just see the hat and his whip alone and they will know what character you are talking about even if they haven’t seen the movies. The hat adds to this rugged adventurer look (and it doesn’t hurt that a younger Harrison Ford looks amazing in it).

Designer Deborah Nadoolman Landis designed the costumes for the iconic Steven Spielberg franchise. Though Harrison himself wasn’t in love with the look as he once stated, “whoever decided that Indiana Jones should wear a felt hat and a leather jacket in the jungles should be shot,” While an exaggeration, it’s understandable that the outfit was more than likely not the most comfortable for the actor. But I think designer Deborah Nadoolman Landis knew what she was doing when she designed this iconic wardrobe.  

Last, but most certainly not least, is what I think is the most iconic hat in film history. It goes to the black pointy witch hat worn by the green Wicked Witch of the West in the most iconic film of all time The Wizard of Oz. Designed by Adrian Adolph Greenberg, the Wizard of Oz costumes are remember by people of all ages. While Dorothy’s blue and white checkered dress with the incredible red ruby heels might be the most iconic piece of movie history, the witch hat is a close second.  

The black pointy witch hat has become the staple for any Halloween witch costume. All you have to do is put on the hat and people atomically know what character you’re trying to be. That says so much about the iconic status of the hat! 


Great Women & Great Hats

This year, 2020, is the 100th Anniversary of the 19th Amendment which gave women the right to vote. Passed in 1920, the 19th Amendment prohibited the states and the federal government from denying individuals the right to vote on the basis of gender. In light of this monumental anniversary, Polly Singer has designed numerous hats that are each inspired by an inspirational or influential woman. Polly’s hope is to highlight these women and their extraordinary accomplishments. Furthermore, Polly wanted to provide some background information about each woman, so each online description gives a mini history lesson. Our hats are off to these outstanding women!



























Maria B







Fall Hat Trends 2019

BreedersCup Hat Tips!

How to Wear Your Hair With a Hat

We often get the question from our clients on how to wear their hair with a hat. Having long hair, I generally wear mine down and natural. There really is no right or wrong way, just whatever is the most comfortable in my opinion.

If you have bangs (or fringe as the British call it), I would suggest pinning them back so that they do not stick out under the brim. Some people will wear their hair back in a pony tail or chignon If you have very short hair, then you need not worry at all.

Hair color wise, I’ve found that redheads, such as myself, can wear almost any color of hat. Pink hats look good on most everyone. I would not advise a redhead to wear a red hat obviously. I always like contrast.

If you are a blond, you can wear a white or cream hat, just put lots of color on the hat to balance things out. A brunette can wear a dark hat, just with a bit of color added. My black and white hats look great on brunettes since the black and white has contrast.

By: Polly Singer

The Cat In The Hat

As a child, one of my favorite books was Dr. Seuss’s “Cat In The Hat”. I never grew up with cats, but now I have many. Combining two of my great loves, cats and hats, it still is a favorite book of mine. Each Christmas, I usually end up with a Cat In The Hat item or two.

The Cat in the Hat was written in 1957. Theodor Geisel, writing as Dr. Seuss, created The Cat in the Hat in response to the May 24, 1954 Life magazine article by John Hersey. Dr. Seuss responded to this challenge, and began work. His publisher supplied him with a list of 400 words, ones that the publisher thought children would be learning in school. His publisher told him to cut the list in half and to try and write an interesting enough book for children. Nine months later Dr. Seuss finished The Cat In The Hat, which used 223 words from the list plus 13 words that did not appear on the list.

In an interview he gave in Arizona magazine in June 1981, Dr. Seuss claimed the book took nine months to complete due to the difficulty in writing a book from the 223 selected words. He added that the title for the book came from his desire to have the title rhyme and the first two suitable rhyming words that he could find from the list were “cat” and “hat”. Seuss wrote the book because he felt that there should be more entertaining and fun material for beginning readers. More than 10 million copies of The Cat in the Hat have been printed. It has been translated into more than 12 different languages.

White House Cat In The Hat
White House Cat In The Hat

In the first book featuring the character (The Cat in the Hat, 1957), the Cat brings a cheerful, exotic and exuberant form of chaos to a household of two young children one rainy day while their mother leaves them unattended. Bringing with him two creatures appropriately named Thing One and Thing Two, the Cat performs all sorts of wacky tricks to amuse the children, with mixed results. The Cat’s antics are vainly opposed by the family pet, who is a sentient and articulate goldfish. The children (Sally and her older brother, who serves as the narrator) ultimately prove exemplary latchkey children, capturing the Things and bringing the Cat under control. To make up for the chaos he has caused, he cleans up the house on his way out, disappearing seconds before the mother arrives. I wish all cats were so helpful!

By: Polly Singer

Perserverance Pays In Hat Design

When I was a little girl, my mother read many books to me. My favorite, “Toodles and Her Friends”, had a cat that went through obstacles, but would always persevere and come out on top. She would always say “Perseverance Pays”. That has always stuck with me.

In designing hats, I am always the most proud of the hats that were the most difficult to design. I will generally design whatever the client requests, even though at the beginning of the project, I have no idea how to “work” the hat.

Victoria at Ascot
Victoria at Ascot

The hat pictured above was designed by me for a client who attending Royal Ascot. We had an idea of what we wanted, but getting the final design and feather color was difficult. She was located on the West Coast, so we never met in person. We would email ideas and photos back and forth. Both she and I ended up being very pleased with the hat. It was one of those that I hated to let leave the studio.

Double Layer Hat
Double Layer Hat

The double brimmed hat pictured was done for a client in Chicago. It was a project that I had never attempted, a fabric covered double brim. We had a difficult time matching up the fabric and getting the right fabric weight. At times, I didn’t know if the project would work, but I perservered on and it did. In part, I knew it had to work because my client is really great and I couldn’t let her down.

Peacock Hat
Peacock Hat

What usually happens is that I fall madly in love with the hats that are the most challenging for me to finish. The hat pictured was done for the Kentucky Derby. We knew we wanted to incorporate peacock feathers, but how? They are notorious to work with since they are flat. I worked day and night on this hat, until it finally came together. The client loved it and said it received rave reviews from everyone she met at the Derby.

What made these difficult hats work was not only effort, but working with great clients. The three mentioned in this article were patient and a had vision of what they wanted. I am lucky to work with such wonderful ladies.

By: Polly Singer

Hats In “The Duchess”

“Men have many ways to express themselves. We only have our hats and dresses” – Keira Knightley as the Duchess of Devonshire in “The Duchess”

Last night, I went with a group of friends to see “The Duchess”. The new movie features Keira Knightley as the Duchess of Devonshire, a direct ancestor of Lady Diana Spencer. Ralph Fiennes is the Duke of Devonshire, who even I can’t begin to describe. Let’s just say that he’s not entirely faithful to his wife as he takes up with her “best” friend (the obvious “with friends like that, who needs enemies?”), and keeps her set up in the house, with all three living in this web of dysfunction. The Duchess, Georgina, is terribly unhappy and frustrated, but what can she do? Women at that time, had no options.

Georgina is intelligent, a political being whose mere appearance can triple a crowd at a political rally. As one of the character says, “Everyone in England is love with the Duchess except her husband”. She became a prominent force in the Whig Party by speaking at rallies and fundraising. She even adopted the Whig colors of blue and buff in her ensembles.

Reynolds Portrait of Georgina, Duchess of Devonshire
Reynolds Portrait of Georgina, Duchess of Devonshire

The Duchess expresses herself through her wit and obviously her clothing. It was said if she showed up wearing a hat or dress style, that it would be copied by all ladies the next day. In fact, she was the star of her day, similar to her direct descendant Lady Diana. Georgina’s hats were stunning, comprised of large black and white ostrich feathers, that often stood straight up in the air, making her stand out in any crowd. The hats she wore in non-public engagements were lovely straw hats, perched lower in the front and higher in the back, again adorned with feathers.

In millinery history, hats were cast off during the mid 1960’s – late 70’s. For many, it was Diana Spencer’s wearing of hats as the new wife of Prince Charles that brought back millinery to the masses. While the average lady didn’t rush out to buy a new hat, it reinvigorated interest in hats.

By Joshua Reynolds
By Joshua Reynolds

Not only were Georgina’s hats and dresses stunning, but she also was known for her hairstyles. She would fashion three foot high “hair towers”. She put pads of horsehair in her own hair, using scented pomade and decorated the top of her hair with ornaments, even ships in full sail. The towers required the help of two hairdressers and took hours to create. For more information on Georgina’s fashion, please visit and go to Discover. Wikipedia also has some interesting historical information.

I would highly recommend seeing “The Duchess”. It will give you a view of period fashion and also make you glad that we live in the day where we as women have many more rights than those living in that period. It is based on Amanda Foreman’s book “Georgina: The Duchess of Devonshire”. For more information visit

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