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Our Favorite Fall Hats Inspired by Icons Like Meg Ryan and Paige Lorenze

We're doing it. We're going to be hat girls this fall.

By
three women wearing three separate hats, one brown fuzzy bucket hat, one tan fedora, one black fisherman cappinterest
Kavu, Overland, Free People

Country Living editors select each product featured. If you buy from a link, we may earn a commission. Why Trust Us?

The minute the temps begin to drop even just a little I start to anticipate fall fashion and a cup of overly sweetened pumpkin flavored coffee, or apple cider, pick your poison. With that being said, I’m already scrolling through Pinterest, Instagram, and flipping through magazines to get a hunch for what my style senses are feeling this season.

Every fall I want to be a hat girl — we all do, don’t lie to yourself. But it seems like I pick one or two hats to keep my noggin warm and stylish and never stray from said hats. So, it’s very important to pick the right one!

I’ve combed through all the runway videos, street wear snaps, and vintage photos for this year’s inspiration to find the hats of the season. Here, you’ll find some of the best picks whether you reach for a classic wide brim hat, cool beanie, vintage cap, or even a trendy trucker hat. We have every style for every occasion. So, when you’re at that Friday night football game or Saturday tailgate, visiting the pumpkin patch, or apple orchard, vintage pickin’ or what have you, don’t forget your newest accessory that will last you through the season.

1

Newsboy Wool Beret Cap

Amazon’s Choice
Newsboy Wool Beret Cap
Credit: Amazon

This timeless beret cap can be bought in a variety of cute colors! This retro-inspired beret will go well with any outfit and can be dressed up for a night out or casual hang with your friends.

2
A classic wide brim hat

Wide Brim Rancher Hat

Wide Brim Rancher Hat
Credit: Fluffy Sense

We're all a little obsessed with Lainey Wilson right now and this hat is perfect for the country singer's look. The light mocha color will go well with all of our fall fits.

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3

Fange Women's Felt Fedora Wide Brim Panama Hat with Tassels

Women's Felt Fedora Wide Brim Panama Hat with Tassels
Credit: Amazon

This hat brings a bohemian twist on a fall classic: the Panama hat. From a variety of colors to choose from, from olive green (shown) to khaki and wine red, the combination of the tassels and hat is colorful and different. In fact, with this hat you don't need much to make a look work, a pair of jeans and a white t-shirt will already work beautifully!

4
Paige Lorenze Inspired Hat

Teddy Bucket Hat

Editor’s Choice
Teddy Bucket Hat
Credit: WETMT

Looking for a hat that's cute as it is warm? This one if going be perfect. Not to mention it, it's great for a Paige Lorenze inspired outfit this fall and winter.

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5
A little more edgy

Brixton Fiddler Fisherman Cap

Brixton Fiddler Fisherman Cap
Credit: Nordstrom

This fisherman cap has two rope trims on the base of the crown with a rich herringbone texture. Try this with your fave fall outfit and it will be the signature look of the season.

6
A vintage look

Phoebe Slouchy Lieutenant Cap

Phoebe Slouchy Lieutenant Cap
Credit: Free People

Finish your look off with this classic lieutenant style cap. It comes in six different colors to fit your style and the soft wool material is ideal for a chilly Autumn day.

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7
Wool hat for the weather

Wool Sherpa Cloche Hat

Wool Sherpa Cloche Hat

Cloche hats are big this fall! A mix between a beanie and a bucket hat, it will be your new fave fall accessory. The warm sherpa material will stay with you well into the winter as well.

8
A Nora Ephron Inspired Hat

Felted Wool Fedora

Felted Wool Fedora
Credit: Kurt Geiger

The one thing I want to watch during fall? Nora Ephron movies! And this hat reminds us of the one Meg Ryan famously wears in When Harry Met Sally.

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9
A cozy beanie

Carhartt Knit Cuffed Beanie

Knit Cuffed Beanie

While Carharrt has been a beloved brand for a while, these beanies arrived on the trend scene a couple of years ago and the style is here to stay. These knit beanies will keep you warm on the chilliest of days.

10
For a Chic and Sophisticated Look

Pinnacle Wool Felt and Leather Safari Hat

Pinnacle Wool Felt and Leather Safari Hat
Now 30% Off
Credit: Pinnacle

With both leather and felt materials, this hat is the best of both worlds! We think it's perfect for a trip to pumpkin patch or a visit to an apple orchard this season.

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11
For a feminine fit

Pink Du Jour Beret

Editor’s Choice
Pink Du Jour Beret
Credit: Free People

Since the Barbie movie has taken over the world, everyone is inspired by Margot Robbie's outfits, including her adorable pink beret. This hat will add a feminine touch to any fall fit.

12
Rancher Hat

ASN Luna Rancher Hat

ASN Luna Rancher Hat
Now 35% Off
Credit: ASN

Rancher hats are a must for fall. This wide brim one comes with a contrasting velvet trim around the crown and the edge of the hat that adds a cozy feel.

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13
A different kind of bucket hat

Kavu Fur Boonie Hat

Kavu Fur Boonie Hat
Credit: Kavu

Fuzzy bucket hats are in this season. We love how this one from Kavu has more of an outdoorsy look. It will be your new go-to hat for a weekend of camping or sitting by the fire.

14

Quarter Hemp Snapback

Quarter Hemp Snapback
Credit: Seager

If you're going for the western look this fall, we're obsessed with this trucker hat from Seager. Throw it on when your running quick errands or dress it up with a pair of hoops and a chic coat for a Princess Diana look.

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15
A Unique Hat

Idyllwind Maybelle Wool Felt Western Hat

Idyllwind Maybelle Wool Felt Western Hat
Credit: Idyllwind

This rust color and burnt orange are always in our fall color scheme, but the exuberant color is really having a moment this season. The wrapped around bandana and feathers adds a unique touch, too.

16
A Cowboy Hat For Everyone

Sendero Cowboy Hat

Best Seller
Sendero Cowboy Hat
Credit: Sedero

If wearing a big 'ole cowboy hat isn't really your style, this one from Sendero is fit for everyone. Trucker hats and baseball caps are no longer just a last-minute hair fix, they're particularly in-style these days.

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17
A Classic Cap

Filson Double Mackinaw Cap

Double Mackinaw Cap
Credit: Backcountry

The Double Mackinaw Cap is a classic accessory for someone who loves fashion and cool weather. What was considered a convenient and warm hat for cool months back in the day is now considered a look of sophistication and unique style.

18
A Hat that will actually keep you warm

Lands' End Faux Fur Expedition Trapper Hat

Faux Fur Expedition Trapper Hat
Now 38% Off
Credit: Lands End

If you live in an area where fall actually gets pretty cold, you might want to grab this trapper hat. It has an old school look that makes it a fun and unique wear while also keeping you warm!

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19
A Western Wide Brim Hat

Midtown Wide Flat Brim Hat

Editor’s Choice
Midtown Wide Flat Brim Hat
Credit: Stetson

When it comes to handcrafted hats, Stetson knows all. The brand is widely loved for it western wear, and you can probably see why. This flat brim hat is ideal for a dressed up night.

20
The Perfect Black Hat

Idyllwind Midnight Stars Western Hat

Editor’s Choice
Midnight Stars Western Hat
Credit: Idyllwind

This is the hat of our dreams! Pair this with a fun outfit for a concert or a fun weekend antiquing. The black wool looks sleek while the silver embellished conchos add some fun flair.

Headshot of Anna Mahan
Anna Mahan
Associate Commerce Editor

Anna Mahan is the Associate Commerce Editor for Country Living. She finds and shares a variety of the best lifestyle products, from fashion and beauty to cast iron skillets.  

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