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Best Women's Hats for Every Season: Wool Fedoras, Berets, Baseball Caps, Bucket Hats & Sun Hats

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The trick to buying a hat you will actually wear is matching the shape to the season: felt and wool from October to March, cotton caps and buckets for errands, and UPF-rated brims for anything outdoors in summer. This list covers six shapes across a ...
 
Rachael Grassi profile picture
This is the wool fedora I point people to first because it looks far more expensive than it is and the structured brim holds its shape all winter. I wear mine with a camel coat and jeans, and the grosgrain band keeps it from feeling too costume-y. Ch...
Lack of Color Noir Rancher Wool Fedora
 
Rachael Grassi profile picture
When I need a hat for a walk or a gym run, I reach for a lightweight nylon cap like this one because it dries quickly and does not hold sweat the way cotton does. It is under twenty dollars, comes in five colors, and the adjustable back fits a ponyta...
OFFLINE By Aerie Nylon Baseball Hat
 
Rachael Grassi profile picture
A leather beret is the one hat that makes a plain black coat and jeans look intentional. This is a real splurge, and I would only buy it if you will wear it every cold week, but the leather wipes clean and does not flatten like felt. Pair it with a s...
Eugenia Kim Carter Leather Beret
 
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Corduroy is the quiet fall move that lifts a bucket hat out of the beach category. I like this one on cool, bright mornings with a chunky sweater, because the cotton cord has enough body to hold a shape and the dark chicory shade works with almost ev...
Madewell Corduroy Bucket Hat
 
Rachael Grassi profile picture
If a hard wool beret feels severe, this angora knit one is the soft version, with a little fur pom that makes it feel playful. It is lightweight and warm, and the pale gray goes with navy, camel and black. It is on sale as a final-sale piece, so conf...
Eugenia Kim Rochelle Angora Knit Beret
 
Rachael Grassi profile picture
A tweed bucket hat is my pick for a dressier cold-weather day, because the warm camel and gold threads match a wool coat and gold jewelry. It packs down for a bag, and right now it is marked down heavily from its original price. Sale items here are f...
Eugenia Kim Yuki Tweed Bucket Hat in Camel Gold
 
Rachael Grassi profile picture
When I am packing for a trip and every inch of suitcase space counts, a packable sun hat like this is what goes in. It rolls and springs back, the tan goes with every swimsuit and cover-up, and at under fifty dollars it does not hurt if it gets sat o...
Brixton Mitch Packable Sun Hat in Tan
 
Rachael Grassi profile picture
This is the budget-friendly beret, in 100 percent wool felt from a New York hat shop that has sold it for over thirty years. It is soft enough to tilt to one side, and the taupe is easier to style than black. For a first beret that you are not sure a...
Hat Attack Classic Beret in Taupe Wool Felt
 
Rachael Grassi profile picture
The washed cotton makes this look like a cap you have owned for years, which is exactly the appeal, since no stiff new-cap break-in is needed. At thirty-five dollars it is the one I would buy for a bad hair day, and the faded ivy and vintage ivory sh...
Madewell Baseball Hat in Washed Cotton
 
Rachael Grassi profile picture
The geometric crown and pleated satin band make this the fedora for dressing up a dinner or a holiday outfit instead of just a coat. It is deeply discounted right now from its original price, so it is the best value of the splurge hats on this list, ...
Eugenia Kim Harlowe Wool Felt Fedora
 
Rachael Grassi profile picture
Brushed wool turns the baseball cap into a cold-weather piece, and the chocolate tone looks great with cream knits and olive jackets. It is soft, sculpted and warmer than cotton, and I would wear it for errands in November without feeling underdresse...
Eugenia Kim Lo Baseball Cap in Chocolate Brushed Wool
 
Rachael Grassi profile picture
If you want one knit hat that does not look like a gym beanie, this is the one, in rib-knit merino with an ivory-to-black dip-dye. It is warm without itch, and the small gold plate keeps it looking finished. It is a splurge, but it is the only beanie...
Eugenia Kim Frances Merino Beanie in Black Ombre
 
Rachael Grassi profile picture
A straw fedora is the warm-weather version of the wool one, and this packable style takes a roll in the suitcase without losing shape. I like the brown-toned weave, which looks less beachy than the usual natural straw and works with linen shirts and ...
Brixton Roma Straw Packable Fedora
 
Rachael Grassi profile picture
A marine cap gives the same polished-but-playful look as a newsboy, and in camel and gold tweed it works with trench coats and cropped jackets. The structured brim stays crisp and the gold chain adds a little shine, so it dresses up denim without try...
Eugenia Kim Marina Tweed Marine Cap
 
Rachael Grassi profile picture
The budget knit hat for dog walks on freezing mornings, under twenty-one dollars and available in several colors. The ribbed knit stretches to fit over a ponytail or headband and goes in the wash easily. When a hat is going to get lost or muddy, this...
Aerie Ribbed Beanie
 
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With the western trend sticking around, a black felt cowboy hat is the safest way to try it, because black goes with everything from boots to a leather jacket. It is under a hundred and ten dollars, much easier on the wallet than the designer version...
Brixton Sonoran Cowboy Hat in Black
 
Rachael Grassi profile picture
A tweed beret is the fall version of the classic, with texture that picks up the colors in a plaid scarf or a houndstooth coat. It is the dressiest beret on the list and the priciest, so I would choose it only if you already own a good wool coat to g...
Eugenia Kim Ione Tweed Beret in Black and Beige