Hello everyone! 

This is Catherine Kung from The Southern Gloss and I am back to talk about what is arguably the most important fashion statement of the year… if you are a horseracing fan, that is!  As Southerners, the Kentucky Derby is often the highlight of our year. Every spring we celebrate the pageantry of this grand sporting tradition by each selecting our own crown of glory for the occasion: the Derby hat.

While the concept seems simple enough perhaps, to truly make a beautiful fashion statement while avoiding certain pitfalls requires a bit of thought and planning.

We touched on the history of  Kentucky Derby fashion in my last post, so lets dive in to the questions that I get asked the most about The Hat.

1. What is the most common mistake made when choosing a hat?

As with all of fashion, I believe that one of the worst things a person can do when deciding what hat to wear is to limit yourself with a set of rules. For instance, so often I hear women say  “I can’t wear this particular hat because of the shape of my face.”  You will immediately miss out on many fun options that expand your horizons . Instead, choose what excites you and brings you joy! Try something new, whether it is an unexpected shape or color. If you love the hat that you are wearing and feel confident while wearing it, you will look amazing… and you can bet on it.

2. There are so many kinds of hats! What is the difference?

While I am sure that there are more, I personally put them into 4 categories.

  • ·The wide-brim embellished “Southern Belle” style hat will give you extra personal space because of it’s size. This showstopper is a classic! But be warned that in tightly occupied areas it can become tricky to navigate the crowds.
  • The average classic brim (typically not wider than your shoulder width) is flattering for every person and is comfortable and chic. Search out hats with elastic sizing built in to help your hat stay put on from unexpected breezes.
  • Fascinators’ are my personal favorite because they are small and versatile. You can maneuver through crowds  with ease and designs come in so many creative shapes and concepts! They can be firmly pinned in and are often attached to a headband or hair comb.
  • Hatinators’ are a hat/fascinator hybrid. They offer the structure and drama of a hat, with the added securing features of a fascinator, such as a comb and hair band to hold it in place. 
  • Pillbox style hats are the easiest to wear. They are typically very lightweight and comfortable making them easy to forget you even have it on! They style became popular in the early 1960’s. Think Jackie Kennedy and her impeccable style

3. What is a milliner?

A milliner is an artist who specializes in designing and making women’s hats from various fabrics and materials. Christine A. Moore is the featured milliner of Kentucky Derby 144 and 145!

4. What comes first: the hat or the dress?

There is no hard rule. When choosing a Derby week ensemble, I always recommend to start with whichever inspires you first. I have personally attended the Kentucky Derby 6 times. Of those, 3 times I chose the hat first, while the other 3 began with me finding the absolute perfect dress right out of the gate. There is no wrong answer. However, I will say that in reflection of my previous Derby outfits, the most memorable and noteworthy started with choosing the fabulous hat first because it made the biggest statement of the day!

5. How should you wear your hair with a hat?

I you have hair length above your shoulders, it is so no problem to leave it down. (Just think of all the fabulous short cuts back in the 1920’s with the amazing hats of the decade! )

For hair any longer than shoulder length, I highly recommend pulling it back or in a low updo to keep it out of your face. Derby Day festivities call for very long hours and often unpredictable spring weather.  Long curls can go flat with a quick rain shower or even slight humidity, so fuss-free hair is a must for an enjoyable experience.

6. What is the best way to know that your hat matches your outfit or is the right size?

It is very helpful to bring your hat or dress with you while shopping. Around this season, most stores in the Louisville, Kentucky area are fairly accustomed to customers toting around one piece or the other! It makes it much easier to find the perfect match when you aren’t needing to guess.

When making a decision, it is not just coordinating colors that is important, but also consider the texture of the fabric. A crisp, tailored outfit would work well with a structured hat, but a soft and flowing dress may look best with something more whimsical and organic.

Size depends on the person. Any person can truly wear any shape; what matters most is proportion.

7. What if it rains?

If the weather is calling for a less-than-ideal scenario involving water, steer clear of wearing hats with feathers and veiling. They will not hold up to damp conditions well. Sometimes I will have a simple, secondary hat planned just incase the day-of forecast changes last minute.

8. What if I want to make my own hat?

I highly encourage creativity! There are so many online resources and craft supply stores that will truly make the sky the limit if you are feeling more hands-on. It is even a tradition amongst some friends and families every year to come together to creative something one-of-a-kind and special. Consider getting your friends together and host a hat making party! If you are celebrating out of state , throwing a Derby party locally, or tuning in around the world, get festive and celebrate with true Southern flair!


I don’t know about you, but I am feeling so inspired and excited for Derby week. It will be here before you know it, so don’ t wait to start planning!  Stay posted for more interesting fashion conversation coming soon

Bourbon and Roses,

Catherine Kung

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