How to Style Summer Hats | EP 95

This week, Your Favorite Stylist Holly Katz talks about hats – and how to style all types for summer. 

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Let’s keep it real: It is the worst time of year to add something extra to wear as temperatures are at an all-time high. However, a hat is a really fun way to add an extra zhuzh to any outfit. Even if you feel like you might spontaneously combust at any moment. #fire

Here’s a nice truth bomb for you:

Nothing is more in style than keeping the sun off your face, and nothing ages you more than alcohol and the sun.

We know. We hate it too. But dammit, if you’re going to be drinking in the sun, then do it under an umbrella and wear a fabulous hat. That’s all we are asking. It’s not a lot to ask!

When to wear a hat, what kind of hat, what do you do with your hair, when NOT to wear a hat! The hat game can be a confusing one. So, let’s start at the beginning:

Remember, the hat is the star. So don’t upstage it with some crazy ass complicated outfit.

Holly’s Top Hats for Summer (no fashion crimes here):

  1. The Fedora 
  2. The Trilby 
  3. The Baseball Cap
  4. The Wide Brim
  5. The Bucket

(Style Tip: go to Holly’s Pinterest board to see all these hats and styling ideas!)


The classic Fedora is Holly’s favorite for summer. It can be made of straw for keeping you cool, and you can dress them up with a grosgrain ribbon or leather hatband around the crown – and even add a brightly-colored feather or sparkly hat pin! 

She recommends wearing your Fedora by the pool or at the beach with a flowy, sheer kimono over your swimsuit or even over a tank top and shorts. Top it all off with statement earrings, chunky jewelry, and a high wedge sandal – PERFECTION!


The Trilby hat, which looks like a Fedora, has the same crown, but a very narrow brim. The crown is the shape of a teardrop if that helps. To be more specific, it’s the hat Jason Mraz and Bruno Mars wear, and they are both Holly’s boyfriends. #truth #duh

Since the Trilby is like the Fedora, Holly recommends styling it in a similar way. One chic idea is to wear the Trilby with a crop top (not too short!), a long maxi skirt, and a heeled-mule. 


We know what you are thinking: a baseball cap MUST be a Fashion Crime! For sure! But actually, it’s not, in this instance. This is a hat that can be dressed up or down. It never goes out of style.

When you wear it the right way it looks super chic and fashion-forward. We’ve seen it styled in so many different ways – from a dress – and we mean a nice dress, like a cocktail dress – and sneakers, to a bright-colored suit and a chunky dad sneaker. 

Baseball caps can be plain, they can have cute sayings or fun logos on them, and even Trucker hats are back. If you don’t dress like a slob, you can pull this off!


If you go to the beach, you’ve seen wide-brimmed hats (which are PERFECT to protect you from the sun. Or, if you’ve attended the Kentucky Derby or Derby parties, those large, decorated hats are wide brim hats. There are many variations, but mainly they can be floppy or structured. 

Holly prefers a structured brim. You want it to keep its shape when you are wearing it. The floppy one is more casual, and best for the beach or the pool.

For styling, she recommends pairing a hat like this with a crisp white cotton buttoned down for a really cute play on menswear with a high-waisted colorful maxi skirt, and a crossbody bag which we think is a great travel outfit or a day outfit, and you can even wear this into the night.


The Bucket Hat was super popular when ‘some of us’ (ahem) were in high school in the 90s. It’s back again and worn by men and women alike. It has been seen all over the runway and beyond for the past few seasons. We are seeing it every turn!  It’s been shown by Prada and Gucci. And some of the more high-end streetwear brands like Balenciaga and Louis Vuitton. 

This is probably Holly’s least favorite style of hat (#sorrynotsorry), but she will agree that it looks great with the right outfit on the right person! She recommends pairing with denim frayed shorts, a fitted top with a blazer or a jeweled cardigan, maybe a high-top sneaker…. something to make it a little bit more street! 

Hat Brands We Love

Get Episode 95 here!

So now you are ready to be super stylish this summer AND protect your skin and face. We are dying to know how you are styling YOUR summer hats – DM us a photo on social, and we just might feature you!


Hosted by Holly Katz, your favorite personal stylist.

Listen now!

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