Try These Perfect Jennifer Aniston Hat Looks

Jennifer Aniston dons a wide variety of hats in all types of weather.

Most people know Jennifer Aniston for her iconic hair. However, sometimes even Aniston keeps it under cover with the perfect hat. We often associate hats with bad hair days and wanting to remain in the background. Aniston proves that the opposite is true: A well-styled hat can complete an outfit and draw attention to the wearer.

Casual hat looks for daily life

Aniston showcases a black baseball cap that calls attention to her iconic role as Rachel on Friends.

Aniston reveals her sense of humor by showing off her Jennifer Aniston Friends baseball hat. This black ball cap features one of her most popular lines from the show, “We were SO not on a break!” When paired with a Monica sweatshirt, the look reveals that she truly does still love looking back at her time spent on the sitcom.

Fashionable looks for staying cool

Aniston keeps it cool under this straw Panama hat
Aniston stays stylishly hidden behind a fan that matches her crisp straw Panama hat. The contrasting striped hat band and neatly bound edge create a clean look. (Clive Brunskill/Getty)


What better way to stay cool – and look cool – than a Jennifer Aniston beach hat. The nostalgic look of this straw Panama pairs with other light colors to create a fashionably put-together image. Aniston’s dark blond hair matches the contrasting color stripes on the hatband, making it look like this hat was made for her. Women’s Panama hats come in many different finishes, but the slight sheen to this straw gives it an upscale appearance. 

This loose weave Trilby provides just enough shade for Aniston.
The deep warm tone of this loose weave Trilby complements Aniston’s laid-back attitude while on set in New York City. (James Devaney/WireImage)


The chunky loose weave of this Trilby hat adds interest to Aniston’s simple outfit. With a deep pinch crease and a stingy brim, the straw hat looks like it was just grabbed on the way out the door. The wide grosgrain ribbon hatband pairs perfectly with her oversized sunglasses. 

Perfect looks for colder seasons

A black felt Fedora is always a good choice for cool weather.
Jennifer’s favorite black felt Fedora is the perfect accessory for keeping things low-key while shopping in Manhattan in the fall. (James Devaney/WireImage)


For cooler temperatures in the fall and winter, a black felt Fedora offers a bit of warmth while maintaining a stylish look. Aniston’s wide-brim black felt hat has a well-loved appearance with a deep pinch on the crown and front pinch. This hat has been handled, thrown around, and still keeps serving as a functional and fashionable accessory. 

A good quality felt Fedora will stay crisp and neat even in a downpour.
Walking in the rain in the West Village in NYC is not challenging for Jennifer Aniston. Her black felt hat keeps her warm and dry. (James Devaney/WireImage)


Aniston isn’t afraid of a little rain as long as her womens Fedora shelters her. Here, her favorite black felt Fedora looks crisp and sharp. The snapped down brim and flat ribbon bow accentuates the vintage feel. 

This beanie keeps Aniston warm while on set in Colorado.
Aniston chooses a black cable-knit wool hat for a late spring snow while on set. (James Devaney/WireImage)


Perfect for the mountains and snowy weather, this knit beanie keeps Aniston warm while highlighting the color of her perfect hair. The addition of the visor on the front of the hat transforms it. The small addition takes it from a plain beanie to a newsboy flat cap that gently frames her face. 

High-fashion hat looks

It’s no secret by now that Aniston loves wearing hats out and about. She also dons them for fashion photo shoots as she did in this one for The Hollywood Reporter. This perfect Jennifer Aniston hat is a white felt Fedora with a crisp “V” crease and wide, floppy brim. It adds the perfect touch to her elegant but casual styling. 

Brad Pitt Hat Choices

Aniston isn't the only one who loves hats, so does Brad Pitt.
Brad Pitt wears a loosely woven Fedora with a laced brim to a movie premiere with Jennifer Aniston. (Steve Granitz/WireImage)


Although he is generally known for his Brad Pitt Cowboy Hat, you’ll often see Pitt in a wide variety of hat choices. This natural straw Trilby features a leather string hatband, lacing around the brim and minimal shaping. The stingy brim gives Brad Pitt a relaxed “I don’t care” appearance that goes perfectly with his hair and embroidered button-down shirt. 

Hats and headpieces can set the stage for a fairy tale ending.
Madame Tussauds chose to place a headband on Jennifer Aniston’s wax figure, giving Brad Pitt a sweeping Musketeer hat with a feather. (Peter Macdiarmid/Getty)


Although they aren’t real people, the wax figures here tell a story. The headpieces reveal the story of an ill-fated love triangle between the three. Jennifer sports an angelic, bright red bow while Pitt wears a Musketeer-style Cavalier. When you add in Angelina Jolie’s sinister crown, we know immediately that the characters portrayed are from the tale of Snow White. 

The Hat Stops Here

From the popular sitcom Friends to her movie roles, Jennifer Aniston has taken a comfortable seat at the table as a stylish influencer. Frequently seen wearing hats, she is the epitome of casual and natural styling. Her hats are thoughtfully chosen. While they elevate her appearance, they still maintain a “I just grabbed this on the way out the door” look. 

You can grab a Jennifer Aniston hat look for yourself with a variety of different hats. Recreate her style with a Jennifer Aniston bowler hat or a Jennifer Aniston bucket hat. The key is to choose a complementary hat with a bit of vintage style. 

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