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5 Major Mistakes to Avoid with Your Kentucky Derby Hat

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The horse racing at the Kentucky Derby is great and all but if we’re being honest, the real reason we go back year after year is to see the hats!

Obviously we’re a bit crazy for gorgeous, larger-than-life, fancy hats and fascinators, so we’re in heaven at any event that calls for women to wear their finest headpieces. But because we know so much about hats, we can’t help but notice common mistakes that women make in choosing and wearing their Kentucky Derby hats.

Not to fear though – we’re here to help! We’re sharing our expertise to make sure that you feel and look amazing in your next Kentucky Derby hat.


1. Incorrect Positioning of the Derby Hat

Designer, fancy hats for women often have a prescribed position on the head. Frequently, there’s a more decorative side to the hat that is meant to go on either the right or left side of the head. If that’s the case, you’ll see the correct position mentioned in the description of the hat on our website. Exquisite hats from milliners like Philip Treacy and Nigel Rayment are like wearable pieces of art, so it’s important that they’re presented in the way they were intended.

2. Unstable

There’s nothing worse than wearing a hat that doesn’t stay put. It can very nearly ruin your day if you show up in a Kentucky Derby hat that keeps slipping to the side or being blown off by the wind. That’s why it’s critical that you try on your chosen hat beforehand and test out exactly how you’ll keep it in place. Many of our hats include a headband, which is a comfortable way to ensure that your hat stays put. Otherwise, some well-placed hat pins can do the trick.

3. Uncomfortable

We’ve all probably experienced how quickly an uncomfortable pair of shoes can kill a good time, but you should know that the same goes for Kentucky Derby hats. When you go to the trouble of purchasing and wearing a beautiful, fancy hat, you want to show it off all day. But if it feels uncomfortable in any way, you’re likely to take it off and then be forced to hold it or find a place to put it. Instead, we recommend trying on your hat and even wearing it around the house for an hour or two to make sure you’re going to enjoy wearing it on Derby day.

4. Wrong Shape & Size

Just as some clothing silhouettes flatter you while others are all wrong, some hat types work better for you than others. Here are a couple of quick guidelines that will help you steer towards the most flattering designs:

●    If you wear glasses or know you’ll be wearing sunglasses to the Derby, choose a hat with an upturned brim.

●    Longer faces look best in shorter, rounder hat shapes that sit slightly to the side.

●    If you have a round face, go for an angular hat with a vertical silhouette to elongate your face.

●    For squarish faces, soften the lines with curved hats that have wide, floppy brims.

●    Heart-shaped faces look best in hats with shorter, slanted brims and interesting angles

For customized advice on which hats would look best on you, don’t hesitate to get in touch with us.

5. Doesn’t Fit

A sad truth that hat lovers must accept is that all hats are not for all people. The fact is that our head shape and size mean that some hats are simply not for us. If you try on a stunning Kentucky Derby hat that’s love at first sight and it’s too tight around your head or is falling off because it’s too big, then it’s best to cut your losses quickly and remember that there are plenty of fish in the sea. Believe us when we say we’ve tried to force an ill-fitting hat before and have always regretted it. The good news is that there are hats out there for everybody, so keep looking.


Find the Best Hats for the Next Kentucky Derby Event

By avoiding these common mistakes with your Kentucky Derby hat, you’ll be able to get the most out of that big day. You’ll also be able to find the perfect hat for you when you browse through our complete selection. The right hat can make you feel like a star and that’s exactly how we want all of our customers to feel. In your perfect Kentucky Derby hat at the races.

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