In 1865, at the age of 35, John B. Stetson founded the John B. Stetson Company in Philadelphia, after a trip west that had him making felt hats on the trail, where a fellow traveler bought one on the spot. The hat he put into production was called the Boss of the Plains: a 4-inch rounded crown and a brim up to 3 3/4 inches, built to keep sun and rain off a working man. That is the shape behind all the cowboy hats for women in this edit, however much the colors have changed.

Women were wearing it early. Ranch women dressed for practicality first, and the hat was there for shade. Annie Oakley then turned a wide-brimmed Stetson into the picture of the bold Western woman, and the rodeo stars of the early 1900s added the flash. The revival is recent and loud: in 2024 the cowboy hat showed up at the Oscars, at Paris Fashion Week and on the cover of Vogue, and it has not really left.

Straw is where I would begin in October, worn over knits and dark denim while the days are still warm. The Brixton Laredo in bone has a cattleman crown and a double wrapped leather band, and the Lone Star in Texas Gold is the warmer, sunnier version with a pin on the band. The Free People Panama is natural Ecuadorian straw with an upturned brim, and the Finca in cream is toquilla straw with a wired brim you can shape. For something sturdier, I would look at the Stetson Los Alamos, which comes with a chinstrap for windy days, or the Bryce with its Gus crown.

Before you commit, put the hat on in front of a mirror with your hair the way you wear it most days. The brim should clear your eyebrows and the crown should sit level, not tilted back.

Raffia has one big practical advantage: it travels. The Brixton Odessa, in tan and in Italian clay, is crochet raffia that packs flat and springs back, so it can ride in a carry-on for a fall weekend away. The cattleman crown and wire brim mean you can still shape it once you land.

Brands that grew up around hats tend to get the weave right. Lack of Color was founded in 2011 by the Australian duo Rob and Tess, and its Raffia Cowboy Hat comes in natural and in a chocolate-brown Coco, both with an upturned brim. I would wear the Coco with a camel coat and straight-leg jeans, since the dark weave looks like October. The Helen Kaminski Gwen is hand-woven raffia, and raffia can be steamed back into shape, which is good news if the crown gets squashed in a bag.

The San Diego Hat Co. pieces are the playful ones. The Dune has a turquoise bead band that looks right with white denim, and the Cutwork Rancher in brown has a cutwork crown and braided band for a little air. Free People's Rocky is open-weave and natural, structured enough to hold its curve.

Run a finger along the inside of the brim and the sweatband. Woven hats should feel even, without sharp ends of fiber, and the brim should spring back when you press it gently.

What I would skip: a raffia hat with a very loose weave if you expect rain or a crowded subway, because it will lose its shape first.

The name deserves a word. Ten-gallon first appeared around 1925, and one theory says it is a garbled version of the Spanish galón, the narrow braided trim that sat around a sombrero crown. Whatever the truth, the hats below are nowhere near that big. They are felt, in the shades of sand, oat and toast.

The Brixton Mesquite Cozy in khaki is a mohair-wool blend with a grosgrain band, soft enough that I would wear it with a chunky cream sweater. Its sibling, the Laredo WTHR GUARD in khaki, is water-repellent Australian wool felt with a suede band, which makes it the one for a damp walk on a gray morning. Janessa Leoné's Nash in camel is stiffened wool with a 4 inch brim and crown, UPF 50+ and made in the USA, finished with a gold D-ring on the band.

Mossant makes the lived-in ones. The Hopeful Dreamer in cream is distressed felt with layered bands and metal charms, and the Down The Road in tan has a creased crown and braided trim. The Manela Ethernal in camel and Bronson in cream are the cleaner, classic shapes, with a pinched cattleman crown on the Bronson. The ASN Nomad in rust brown has a braided belt band and a 4 in brim.

Hold a light felt hat up to a window. The color should look even, with no patchy spots, and the brim should have a steady curve from side to side.

What I would skip: a cream hat for a rainy commute with a pale coat, since felt shows every drop and smudge.

Felt is where Stetson began, and Buffalo Bill did the rest: within a few years of launching his Wild West shows in 1883, his Stetson-capped image was on signboards from San Francisco to Saxony. Black and brown felt still carries that stage-ready weight.

The Stetson Open Road Royal Deluxe in black is handmade in Garland, Texas, with a hand-pressed cattleman crown and a satin lining. It is the one I would keep for years. Brixton's Sonoran comes in black and in brown, hard-stiffness wool felt with a teardrop crown and a faux snakeskin band, plus an adjustable strap under the sweatband for a snug fit. Manela's Boss Premier in brown has a pinched crown and sharply upturned brim, while the Rancher 4X in black is a clean cattleman with a curved brim.

For a softer mood, the Lovely Bird Montana in rust brown has a dipped crown and a band of silk and suede with turquoise stones. The Billabong in brown is wool felt with braided rope trim and a metal badge, and the Tasha in black has a leather band with polished studs. I would pair any of these with a slip skirt, tall boots and a worn leather jacket.

Check the fit by shaking your head gently with the hat on. It should stay put without leaving a mark across your forehead. If it sits loose, a hat tape in the sweatband helps.

What I would skip: a stiff black brim with a full coat collar, since the two will fight for space around your neck.

The early rodeo stars did not go quietly. Elle describes the women of the early 1900s as dazzling the crowd with over-the-top stunts, and the sparkle came with them. That is the line I would trace to this last group of hats, all about color and detail.

The Brixton Odessa returns here in Primal Green and in Tan with sunrise blue embroidery, both crochet raffia with a shapeable wire brim. The Van Palma Diego is a blue woven straw hat with a beaded semi-precious stone band, handwoven in Ecuador. The San Diego Hat Co. Coney in lavender and Zuma in multicolor stripes are paper straw with a 3.5 in brim, light enough for a long day out.

For fall, I would look at Free People. The Ryder in butter yellow is wool felt with a dipped crown and an exaggerated brim, and the Forever Western in black has a chain and iridescent star cutouts. Tasha's version in taupe has silver conchos on a leather band.

Treat the brightest one as your only accent. A yellow or lavender hat looks best with a quiet outfit, such as gray knit and straight jeans.

Test the trim by pressing on the studs, stones and chain. Everything should sit flat, and nothing should catch your hair.

What I would skip: a heavily decorated hat with a patterned shirt, because the pieces compete.

Here is what I would do. Choose the color of your coat first, then pick a hat that sits a shade away from it. Try straw now while the weather holds, and keep the felt for the first truly cold week.

Then check the three things that matter: the brim clears your eyebrows, the crown sits level, and the band does not pinch. If all three are right, the hat is yours.

John Stetson sold his first hat to a stranger on the trail, and I like to think that stranger was only after shade. That is still the best reason to buy one for yourself.