Kentucky Derby Hat Guide

  • , by Alex Torres
  • 7 min reading time

These Hats Will be in Style at the Kentucky Derby this Year

Heading to the Kentucky Derby this year? It's an exciting event and your chance to be seen and rub elbows with elite celebrities- because everyone wh's anyone goes to the Kentucky Derby.

But this means you have to look your best-and that means wearing a stylish hat for the Kentucky Derby to top off your suit.

How to Dress For the Kentucky Derby

Going to the Kentucky Derby means dressing up nice, it's part of the experience. And you really want to look stylish and sharp-that means not only wearing a nice suit, wearing the right Kentucky Derby hat.

Your hat needs to not just be in style, it needs to make you look smart, in touch and debonair. But which one to choose? There's a handful of hats that you can wear to the Kentucky Derby but not all are excellent choices. Take your time and pick the right one.

If it's your first time or you need a refresher, here are some tips on dressing up for the Kentucky Derby.

The Kentucky Derby is a big social event, which means you have to dress nice, and that includes wearing a nice hat.

Everyone who's anyone at the Kentucky Derby always dresses up because this is not just a horse race, it's a social event where people go to be seen and enjoy the fan fair. So, a nice suit or fancy dress accented by an even better hat is the way to go.

What Hat Should You Wear at the Kentucky Derby this Year?

What hat should you wear at the Kentucky Derby this year? Styles change fast nowadays and sometimes what's in last year is passe the next. Stay on top of changing hat trends and look at what's worked in the past. As always celebrities and those in the know will probably be setting the style trend. So, take a look at who wore what hat at the Kentucky Derby last year.

The Tahoe by Scala Hats is a classic Kentucky Derby hat.
The Tahoe by Scala Hats is a classic Kentucky Derby hat.

What Styles Make the Best Kentucky Derby Hats?

Count on similar hat styles being all the rage this year at the Kentucky Derby. The classic Kentucky Derby hats are straw fedoras, wool felt fedoras, bucket, and even boater hats if you really want to tip your hat to the golden era of horse racing. During the times when the derby (and horse racing in general) were enjoying their heyday, boaters were all the rage. So, were fedoras in fact. So, you can't go wrong wearing either one.
Homburg hats are stylish options for the Kentucky Derby.
Sinatra's famous fedora hat
Felt fedoras have stylish charm ideal for the derby crowd.
Thomas Shelby's hat worn in Peaky Blinders is called the
The Shelby is a classic flat cap with real authenticity.
The Irish Flat Cap, with a three-panel desing and tweed pattern, can really enhance your style.
The Irish Flat Cap looks great with casual suits.
A straw fedora is an excellent option for the Kentucky weather.
Boaters are a classic choice.
The shorter brim straw fedoras have a style perfect for summer suits.

Sports celebrities like Tom Brady and David Ortiz have worn fedoras at past Kentucky Derby events, with Tom Brady opting for the heavier felt option, and Ortiz choosing the more sensible straw.

You should also consider the flat cap. That's right, this is yet another throwback to the era when horse racing was truly king. Flat caps are sporty, sharp and they give your casual suit an elevated sense of style that takes it from ordinary to extraordinary very quickly. Especially when your wearing a lighter suit, a flat cap or Shelby can really give you an air of grounded sophistication, and that look is in this year.

Obviously, it depends on what you are wearing. You want to choose a hat that completes your outfit and takes it up a level. But to get you started here's a great selection of the best hats to wear at this years Kentucky Derby:

Straw Fedoras

The best hat choice for this year's Kentucky Derby might just be the straw fedora because it is so comfortable in the heat. Light and breathable it's going to be a pleasure to wear, and you'll keep cooler. A heavier felt fedora might make you sweat a little too much in the southern heat. Straw fedoras are also the perfect complement to lighter, warm-weather suits especially linen and cotton. They just look better, asides from their above-average performance in warmer climes.

The straw fedora is a true classic Kentucky Derby hat. It matches just about everything and it is truly a comfortable hat to wear. Wear it with your summer suit, whether it's light gray cotton, pin-striped linen, or wide pinstriped tuxedo, you will look fabulous and right at home in one of these stylish hats. Here are a few to check out now...

The Tahoe by Scala Hats is a classic Kentucky Derby hat.

Boater Hats

A real classic and a nod to the era of horse racing, the boater hat is a classy choice with style to spare. This hats also looks great with lighter summer suits and it can really give you a unique and authentic look. Where can you get a boater hat? Click here to view a selection of authentic straw boaters.

The navigator boater hat is a great choice for the Kentucky Derby.
The navigator is a classic Kentucky Derby hat.

Flat Caps

The flat cap is the perfect choice for those who want something more casual. We suggest wearing a lighter cotton flat cap to accent your suit. Or, give your look some flair and opt for a more stylish Shelby flat cap. Opt for a brown or gray plaid flat cap, or get fancier and more stylish with a newsboy cap. That will add character and charm to more upscale suits and ensembles.

The Shelby hat is another incredible option to look amazing in a flat cap.
The Shelby hat is a classy option for the Kentucky Derby.

Felt Fedoras

A felt fedora is another great choice for the Kentucky Derby. If you are wearing a really classy suit, there's only one hat option for you, and it's a felt fedora. Check out our fedora and hat guide to find a shape that's right for you, and then browse these top choices for fedora hats.
the Chatham is an excellent choice for your Kentucky Derby suit.

A wide brim fedora can accent a stylish suit, while shorter brims look sportier and sharper.

View more articles

  • Stetson Hats

    10 Ways to Incorporate Stetson Hats for Men into Your Everyday Wardrobe

    Read more 

  • Blog posts Warm Up Your Winter Look with These Trendy Wool Hats for Men

    Warm Up Your Winter Look with These Trendy Wool Hats for Men

    Read more 

  • Trilby Hats The History and Significance of this Classic Accessory

    Trilby Hats: The History and Significance of this Classic Accessory

    Read more 

  • Party in Style How Customized Fedora Hats Are Elevating Events and Parties

    Party in Style: How Customized Fedora Hats Are Elevating Events and Parties

    Read more 


Forgot your password?

Don't have an account yet?
Create account