How to Pick the Perfect Derby Hat for Men

Stephen Romero - June 18, 2022

If you’re planning on attending the Kentucky Derby, you probably already know that it’s all about dressing to impress — and at the Derby, there’s no better way to do this than with a hat that makes you look good and keeps your head cool in the heat. But where do you start? Should you go with something traditional or go bold? There are plenty of options out there for every man — so don’t sweat it too much as long as you follow these five guidelines for choosing the perfect mens derby hats .

Picking a Style

Stetson, Borsalino or Trilby? Derby hats come in three main styles, each with their own unique look. Stetsons are popular among those who want a more conservative look and appeal more to those whose hairline has receded somewhat. If you have a full head of hair and want something a little bolder, it might be time to wear a Borsalino derby hat. Or, if you prefer something more casual and fun then give a trilby derby hat an audition. It’s okay if none of these really seem like your style – there are plenty of options when it comes to derby hats for men: panama hats, fedoras or perhaps one from Neff Headwear collection like , Elwood or Woody Derby.

Picking a Size

Mens derby hats come in a variety of styles, but they typically fit close to your head and are shaped like a traditional fedora or baseball cap. Some styles have narrow brims, while others are more circular; generally speaking, though, mens derby hats should sit low on your forehead and not extend too far back over your crown. As with choosing a fitted dress shirt, you want to choose a size that fits comfortably but still looks sharp (you wouldn’t wear an XXXL sized polo-style shirt if you were in great shape—don’t do it with a derby hat either).

Picking a Color

The Bowler is an iconic hat that is historically worn by men. Picking the right color and style of bowler will have you looking sharp at the Derby. Unlike fedoras, the main focus of a derby hat is color. With so many different shades, patterns, and shapes it can be hard to know where to start when picking out a derby hat. Start with your own hair color and determine what colors look best on you. Then decide what type of clothing or suit you’ll be wearing; matching your bowler will help tie everything together making you look like a gentleman rather than just another guy at the horse races sporting one of these fantastic hats!

Determine If You Need an Adjustable Band

There are two main types of Derby hats: the derby and the bowlers. The bowler hat is typically worn by men and has a band that can be adjusted using a buckle or buttons. This type of hat is ideal if you have a smaller head or plan on wearing it tilted downward. The derby hat has one standard size, so adjust the fit by holding down on one side of the crown while pulling on the other side until it’s snug but not too tight. If your head is larger than average, opt for a wider brim (3 inches) to make you look taller and thinner. These hats are available with or without creases in the crown, so choose whichever looks best on you.

Choose Your Fabric Wisely

Most of what makes your Derby hat look, feel, and fit better is all about how you wear it. Different styles of hats will mean different styling needs, but here are a few general tips that can help you make sure your hat fits well and is ready for race day: Style Your Hair: This might seem like a no-brainer, but if you want to look stylish in your Derby hat then make sure you’ve taken care of any loose hairs and styled them into place before putting on your lid. Choose a Fitted Fit: If you want to wear your derby full (or a little bit above) rather than tapered or low (worn really low), then choose a fitted fitting derby.

Styling Ideas

Hats are tricky. People have been known to over-accessorize and choose styles that simply don’t match up with their outfit. In fact, we even had a guest columnist on our site back in June who made that exact mistake when he wore a pink hat with his pink tuxedo at his wedding. As men’s fashion bloggers, we want you to stay away from wearing any sort of pink hat (or any other colors) because they simply clash too much with your outfit. Instead, focus on solid colors: reds, blacks, navy blue and grays will all look great at the Kentucky Derby—and unlike colored hats, they can also be paired with anything you choose!

More Tips for Great Style

As men, there are certain races where wearing a hat is appropriate and others where you may want to consider skipping it. The Kentucky Derby, for example, is a race that calls for either a straw derby hat or one of many styles of top hats; by contrast, most Preakness attendees in Baltimore opt not to wear hats at all. Whatever your plans may be, don’t fret—there are lots of options out there. Just use these tips and guidelines as a guide so you can choose something great and make everyone wish they had your style!

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Stephen Romero

Stephen Romer has decades of experience and expertise in consultative marketing, sales, management, tech, and lifestyle. He has given notable seminars, featured on media for his exceptional writing skills.


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