Get A-Head Of Fall 2021’s Biggest Hat Trends

Bella Gerard
Get A-Head Of Fall 2021’s Biggest Hat Trends
Photo: Courtesy of Von Dutch; Lanliebao; Lisianthus; Adobe. Design: Cierra MIller/STYLECASTER.

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Let’s make one thing very clear: 2021 is officially the year of over-accessorizing. After being stuck inside for most of 2020, fashionistas are itching to pile it on and head out, showing off every new thing they bought while staying at home. Hats are no exception and that’s why the fall 2021 hat trends below are all seriously cute. And a little extra, TBH.

I didn’t use to be much of a hat gal, but after treating myself to a wide-brimmed beauty a few months back, I became hooked. As someone with pesky melasma, it’s important for me to shield my face from the sun all year round, so getting to do so with a cute hat makes me even happier. Bucket hats are still trendy this season—and not just for the beach! There are some seriously cold-weather appropriate versions, plus a few other fun silhouettes to consider adding to your collection, too.

Cowboy hats, for instance, have officially crossed over into the fashion world for the fall season,  just as cowboy boots did during the summer. Seriously, you need one for yourself. No, you won’t look weird! The same goes for trucker hats—and I promise, they’re way cuter now than they were back in the early aughts, although I loved ’em then, too. You can never go wrong with some Von Dutch, baby! 

The key to wearing hats is to consider them from the get-go as you put together your look; if you throw one on atop an already heavily styled outfit, you’ll definitely be doing too much. I don’t want to spoil all the fall 2021 trends below, so with that, read on for your head’s hottest must-haves, plus a few good options to order now.

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The Bucket

Ah yes, the bucket hat trend lives on for the fall—only now, it’s getting a luxe upgrade. Swap your basic bucket for one that’s made from denim, pleather or vinyl this season. Or, choose one with quilting for a slightly preppier vibe. Whatever makes your bucket stand out will put you a-head (I’m sorry) of everyone else.

STYLECASTER | 2021 Hat Trends

Courtesy of San Diego Hat Co.

Quilted Rain Hat

This Quilted Rain Hat from San Diego Hat Co. is giving me all the fall vibes. Plus, now you can keep your hair looking cute even if it rains.

STYLECASTER | 2021 Hat Trends

Courtesy of Newhattan.

Cotton Bucket Sun Hat 

This Cotton Bucket Sun Hat
makes me want to be a skater girl. This pick is proof that denim makes just about anything look cool.


STYLECASTER | 2021 Hat Trends

Courtesy of Lanliebao.

Waterproof Rain Hat

If a leather hat is too pricey, consider a vinyl option! This Waterproof Rain Hat
has a high-shine finish that feels so on-trend for fall.


The Trucker

With all the early aughts trends back in style right now, it was only a matter of time before trucker hats came back, right? These new iterations are just as bold as the ones you remember, so feel free to dress them up with a slip dress or down with jeans and a leather jacket.


STYLECASTER | 2021 Hat Trends

Courtesy of Von Dutch.

Classic Baseball Trucker Cap

When it comes to trucker hats, Von Dutch reigns supreme. I mean, how could you not pick up one of their classic styles? This Baseball Trucker Cap
is one of the OGs.


STYLECASTER | 2021 Hat Trends

Courtesy of Mitchell & Ness.

 Los Angeles Lakers Trucker Hat

Trucker-style hats already have tons of retro appeal, but this Los Angeles Lakers Trucker Hat brings all the ’90s energy.

STYLECASTER | 2021 Hat Trends

Courtesy of Bun Maternity.

Mama Trucker Hat

I love the lettering on this Mama Trucker Hat because it makes such a statement. That said, the navy colorway means that it will go with tons of outfits.

The Cowboy Hat

If you thought that cowboy boots were the only western-inspired piece that the fashion set has been loving this year, think again! Cowboy hats are officially trending for fall 2021, so giddy on up! Choose one that comes in a neutral shade like black, tan or white and wear it with everything.



STYLECASTER | 2021 Hat Trends

Courtesy of Kangaroo.

Cowboy Hat

Starting off strong here with an all-black option. This hat
from Kangaroo works for a western-themed party, yes, but it also looks chic for everyday wear. Trust me!

STYLECASTER | 2021 Hat Trends

Courtesy of Wyeth.

London Hat

The No White After Labor Day rule doesn’t apply when you’re in the Wild, Wild West. Style this London Hat with an all-black ‘fit for an intentional contrast.


STYLECASTER | 2021 Hat Trends

Courtesy of Lisianthus.

Felt Wide Brim Western Cowboy Hat 

For a touch of color, consider this Felt Wide Brim Western Cowboy Hat
. The turquoise stones totally add to the ranch-inspired flair.

A version of this article originally appeared in October 2020.

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