27 Stylish Hat Inspirations For This Fall

By: Avatar photo Andy Jones Updated: Mar 10, 2024


It’s time to look for the hat idea you’ve been thinking about all summer. It’s autumn and the weather is starting to show some changes. From extra wind and cool breeze, you may be looking for ways to stay warm and keep your hair in place. One attractive way to look good and add style to any autumn outfit is to wear a hat.
Choose a hat that will improve your look and trick people into thinking you’re a fashionista. To help you choose trendy looks for this autumn season, we have compiled 27 outfits that look great with a hat.

Craving Attention? These 27 Stylish Hats Will Have All Eyes on You

27 Stylish Hat Inspirations For This Fall

1. Stylishly Bohemian

Stylishly Bohemian

Add a dash of charm to your bohemian look with this cute light-beige hat with a dark brown trim around it. The hat is small enough to stay out of your way, but adorable enough to bring the best attention your way.

2. The Most Stylish Girl in Town

The Most Stylish Girl in Town

Source: ugg.com

You never know if you can pull of a look until you try. This trendy cartwheel hat is the ideal accessory for almost any outfit. From classy to casual, it’s the hat that can fit in perfectly, no matter what.

3. Keep the Sun Away

Keep the Sun Away

Source: zappos.com

Every girl needs that perfect woman’s hat to wear during the autumn. This floppy wide-brimmed hat is so adorable that it makes this hat idea an extremely fun one.

4. Stay Trendy Through Any Weather

Stay Trendy Through Any Weather

This is the adorable hat that belongs in any lady’s wardrobe. Bold and beautiful, it pairs nicely with any look, but can you just imagine wearing it a pair of cute overalls? That’s a hat idea that any girl can get with.

5. So Beautiful, So Chic

So Beautiful, So Chic

For the darlin’ who belongs on a Parisian run-way, this boater hat is the ideal accessory for almost autumn outfit. Whether you wear it with your dark brown hair down or with a low, loose bun, it will help you ace any look.

6. I Welcome Bad Hair Days

I Welcome Bad Hair Days

Every girl needs a hat for those bad hair days and when it comes to one that you can depend on, a light-grey boater like this one will keep you looking trendy, no matter what may come up in your day.

7. Boating in the Fall

Boating in the Fall

This hat is perfect for that outdoor occasion in the fall with its classy black ribbon and elegant design. Whether you’re choosing your holiday pumpkin or going sailing while the weather is still fresh, this hat will be the ideal match for you.

8. Ready to Slay

Ready to Slay

Just because it’s time to work, it doesn’t mean that you can’t have a little fun. This gray hat will combine beautifully, even with office wear.

9. Tame the Mane

Tame the Mane

A windy day doesn’t have to mean crazy hair; at least not with this adorable trilby that will look good on the classiest of ladies.

10. A Night in Paris? Yes, Please!

A Night in Paris? Yes, Please!

This classic, floppy hat should be your travel companion. It will ensure that you’re ready to impress, no matter what may happen on your trip. Keep it with you and never let it leave!

11. Flirty, Fun, and Fabulous

Flirty, Fun, and Fabulous

This adorable hat should be worn on the days when you want to look fashionably cute. Fun to wear, cute to look at, and easy to match with almost anything, it’s the perfect hat to add to your autumn wear.

12. Autumn Colors Look Good on You

Autumn Colors Look Good on You

Source: inonit.in

Everything about this look is classically beautiful for the fall, but the addition of the beige hat, makes it the perfect look for the season when the leaves and weather are changing.

13. Ready for Business

Ready for Business

Nothing looks as put together as black on black. This black hat pairs perfectly with the black top and can be used for a meeting with your clients, a brunch with friends, or a day out on the town.

14. Is it too late for festival wear?

Is it too late for festival wear?

If you plan on attending autumn festivals, don’t forget the hat that demands to join in on the music. This broad-rim hat will complete the trendiest festival wear.

15. “Sex and the City” Style

Can’t you just imagine Carrie in a hat like this? From the color to the feather, it should be the number one hat in your autumn wardrobe.

16. Going Incognito

Going Incognito

Whether you want to stay low-key or simply like pulling off mysterious looks, this fancy black hat paired with large shades will compliment any fashionista’s outfit.

17. The Cherry on Top

The Cherry on Top

As if this look wasn’t adorable enough as it is, the bowl-shaped hat completes it entirely. Whether you have brunch with girlfriends at noon or a gig to perform at 5, this hat should always go with you.

18. Subtly Beautiful

Subtly Beautiful

This is the look that sneaks up on you. At first glance, it looks comfortable, but when you look at it again-especially that gorgeous gray hat-you realize just how elegant it is.

19. Out on the Town

Out on the Town

Source: shopbop.com

All work and no play is no fun which is why you will want to add this hat to your outfit during the week, to make sure you are always ready for unexpected happy hours.

20. THAT Perfect Accessory

THAT Perfect Accessory

Source: i.pinimg.com

Every outfit calls for that last finishing touch and when it comes to this one, this floppy hat ensures that you will look fashionably beautiful for any occasion.

21. She’s Got It

She’s Got It

This hat works for a number of reasons, both to keep the sun out of your face and for you to look extremely stylish. No matter what you have planned for your day, this hat will fit right in.

22. I’m A Star

I’m A Star

There’s nothing like strutting around confidently with a hat like this one. It’s the kind of hat that says, I know what I’ve got and this is how I show it.

23. Take Me Away, Cowboy

Take Me Away, Cowboy

This gray hat is the kind you want to use in the great outdoors. Reliable, beautiful, and stylish as can be, it’s the hat that you can depend on to keep you looking trendy, no matter what you’ve got going on.

24. Dolled Up

Dolled Up

Source: chicwish.com

This is the hat that you’ve been dreaming of. It’s a hat that should be worn throughout the year. From its perfect color to its stylish look, it can be worn for almost anything you have planned.

25. Carmen San Diego Wore It First

Carmen San Diego Wore It First

For any little girl who grew up on Where in the World is Carmen San Diego, you can’t deny you always envied her look. Envy no more! This hat will make you feel like Carmen, no matter where in the world you are.

26. All Eyes on You

All Eyes on You

As if this complete look wasn’t trendy enough, this black hat paired with those perfect glasses says that you aren’t afraid of taking risks and people will notice it!

27. Ready for the Day

Ready for the Day

The hat that you can take with you anywhere. From waking up to grab a coffee to catching up with friends over a bite to eat, it’s the accessory that will always keep you looking trendy. If you have one hat idea this autumn, make it this one.

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About the AuthorAvatar photo
Andy Jones

Andy focuses on getting readers familiar with the latest and trendiest hairstyles. There’s pretty much no style she has yet to try, and her mission is to help everyone find the perfect look they seek. When Andy is not gushing about hairstyles, she spends most of her time reading through her giant collection of sci-fi books or watching old Star Trek shows. See all articles from Andy.