A Year-Round Guide to Women’s Hat Styles

How and when to wear these iconic women’s hat styles

From Jackie O’s classic pillbox hats to Josephine Baker famously breaking gender roles by sporting a top hat with a tuxedo, to Lady Gaga’s famous Pink Hat – women have been using head wear to make statements for generations. With an endless array of hat styles to choose from, it’s important to know when to wear what so you’re making the right statement with the hat you choose to wear. That’s where we come in. Read on for a quick go-to guide on when and with what to wear some of the most iconic and illustrious women’s hat styles. And as a bonus, we’ve included a little history about each style so you can brush up on your trivia knowledge!

Victorian and Steampunk top Hats

As a symbol of urban respectability in the 19th century, there has never been a more sophisticated and dominating hat in fashion than the top hat. When first worn in 1797 by the man credited as its inventor, haberdasher John Hetherington, it was documented that “a passersby panicked at the sight, several women fainted, children screamed, dogs yelped, and an errand boy’s arm was broken when he was trampled by the mob.” Josephine Baker, iconic jazz entertainer and civil rights activist, inspired similar shock and awe by breaking gender roles when she famously sported a tuxedo and top hat in the 1932 production of La Joie de Paris

Although the Victorian wide-brimmed, tall-crowned top hat was historically made from felted beaver skin, today’s styles include brown, black, gold or even white leather and mesh. To add even more character and personality to the attention-grabbing accessory, a subcategory of Steampunk top hats was created. Steampunk top hats embody the truest essence of fantasy and creative exploration with their limitless usage of color, material, and hat band decor or trinkets. 

If you want to make the ultimate impression that causes an uproar of attention, then Victorian or Steampunk top hats are the way to go. Traditionally considered a men’s hat style, wearing a top hat is a great way for a woman to bend sartorial gender roles in a bold, sexy, and fashionable way. Pair it with a tailored tux to make a statement at a formal event, or with a boho chic dress to stand out from the rest of the festival crowd. 

Wide-Brimmed Fedoras

The fedora first hit the fashion scene in 1882 when the famous actress Sarah Bernhardt wore one in the play Fédora. In the 1920s, Prince Edward of Britain showed men that they too could style the iconic handmade hats. The fedora hat has since become associated with late night activity of gangsters, musicians, actors, and models. It has an edgy yet sophisticated and elegant look, which is precisely why you’ll see Beyonce, Chrissy Teigan, and Lupita Nyong’o sporting this style. 

The type of fedora a woman wears completely defines her personality and style statement. A wide-brimmed fedora can add elegance or boho flair (depending on the make and material of the hat) to your outfit. It also is an excellent choice when you need good sun protection along with style. Adding a fedora is a great way to dress up a more casual outfit, or spice up your favorite dress that you’ve worn a few too many times. The wool and felt versions are perfect for the fall and winter, whereby straw fedoras offer a lighter more breathable option for the summer. 

Trilby Fedoars

Just as all fashions evolve over time, the wide-brim fedora has been modified into a narrower brimmed version called the trilby. Worn in the first production of the novel Trilby in 1894, the hat regained popularity in the 60s, 80s, and once again the 21st century as a retro trend. 

The trilby has a compact but taller crown, which often highlights high-set shallow indents for a stylish, tear drop shape. The brim is curled on the edges and the hat is worn slightly farther back on the head so that it sits at an angle. It’s a great option for the carefree and fun individual looking to accessorize her vintage designer jeans. Wear it throughout the day and seamlessly transition into a formal dinner downtown then a late night jazz club with class.

Cowboy or Western Hats

The first American Cowboy Hat was designed by John Batterson Stetson in 1865 and he called it the “Boss of the Plains.” The straight-sided crown with rounded corners provided insulation for the top of head, whereby the wide stiff brim provided shelter for the face, neck and shoulders from both the sun and precipitation. The durable, lightweight, and waterproof option was made from the highest-quality materials. It quickly became regarded as an investment for the working cowboy (or cowgirl), a statement of success for the city dweller, and the universal image of the American West. 

In this day and age, cowboy and western hats are no longer reserved for the rodeo bronc riders! Instead, the Stetson-inspired designs have been turned into a variety of styles that represent both the allure of the Wild West and the comfort of a ball cap. There are small brim cowboy hats that will make you feel like Calamity Jane, gambler hats that remind us all of Gone with Wind, and more traditional wool, felt, straw, or leather cowboy hats that will complement your favorite pair of boots. 

There aren’t many stipulations as to when and where to sport your favorite western hat style, however there is an unspoken requirement to act like a lady with proper etiquette when doing so. Take your hat off at the table (some would say when you walk indoors), and always remove it during the National Anthem. 

Panama hats

Despite their name, these hats originated in Ecuador and became popular during the historic Gold Rush when prospectors traveled from Panama to California. When admired by the masses, travelers told people they bought them in Panama, and the name stuck. From the 19th century to the 1950s, everyone wore Panama hats as a part of their wardrobe. Today the light-colored, lightweight hats are gaining just as much popularity. Marilyn Monroe, Audrey Hepburn, and Gigi Hadid have all worn this style with pride. 

Panama hats (also known as toquilla straw hats) are similar to fedoras, however they have a central dent in the crown that’s pinched at the front and are made from a variety of straw weaves. Designed in a plethora of shapes to match different face sizes, the Panama hat can be worn with just about anything. Embrace a sophisticated Riviera style or spruce up your outfit for your friend’s summer bbq, it doesn’t matter because these hats are meant to look great day or night. And since they’re a bit more formal than most sun hats, they’re a perfect resort or outdoor event hat. 

Outback Hats

The Australian Outback can be a harsh environment requiring durable yet hardy protection and rugged but supple gear for survival. With these specific needs, the outback hat was designed to ward off the weather and fold up into very small spaces while retaining its original shape. In 1874, the Keir family began manufacturing the original outback hats, called Akubra hats, in New South Wales. The Man from Snowy River wore an Akubra in the well-known movie and has been an icon of mystery, romance, and western allure ever since. 

Similar to cowboy hats the felt, straw, canvas, and leather outback hats add a tinge of excitement and practicality to any get up. They represent adventure and are perfect for hiking, camping, travel, riding horses, or anything that involves roaming the territories outside the city. Wear it for functionality and be seen as a rugged symbol of fun. Just be ready to say what Indiana Jones once said, “Jock! Start the Engine!” because you are sure to be on a ride. 

Pork Pie Hats

Pork pie hats, also called English pastry hats, first came about in Britain around the late 19th century, but became popular in the 1920s after silent film star Buster Keaton wore them in several of his movies. The classic small round hats with a narrow curled-up brim, slightly domed crown, and band fastened around the crease were more recently given attention after Walter White’s alter ego “Heisenberg” wore one in Breaking Bad.To add to the limelight, fashion writer Glenn O’Brien of GQ magazine once said pork pie hats are, “the mark of the determined hipster, the kind of cat you might see hanging around a jazz club or pool hall… a Tom Waits, Johnny Thunders kind of hat.” 

It is suggested that anyone with a long, short or oval shaped face will look good in pork pie hats. Their slightly squatty appearance and colorful bands make the hats a more casual option for sporting events or jazz clubs. The style suits events that emanate culture, such as horse-racing, movie screenings, or art showings. 


Whether the reasoning is ornamental or practical, women have been accessorizing with stylized head coverings since the Egyptians wore conical straw hats in 3200 BC. Since style will forever be evolving, and what was once deemed trendy and all the rage today may be seen as classic or even out-dated tomorrow, we want to mention one more important fact. 

The ultimate truth behind this guide is that every hat can suit every occasion, IF, and only IF,  the head under the material wears it with confidence and class. Yes, there are several styles that fit certain circumstances for practical and/or functional reasons. However, we believe that style refers to a person’s particular way of expressing themselves and we encourage everyone to do precisely that.

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