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When it comes to Kentucky Derby fashion, few accessories make a statement as much as hats do. While horses run for the roses, guests compete to show off their stylish headpieces.
This year’s event celebrates a classic blend of flair and extravagance. Derby goers are eager to flaunt jewel accents and vivid silhouettes.
If you’ll be at Churchill Downs, this guide will help you pick the best Kentucky Derby hats to complete your race day look.
Why Are Hats Worn to the Kentucky Derby?
Wearing hats to the Kentucky Derby is a tradition that dates back to the inaugural race in 1875. Over time, hats became a staple of the derby, adopting more colorful and creative designs.
To date, headwear is the most remarkable fashion symbol in the Kentucky Derby.
Historical influence
The Derby drew inspiration from English racehorses, where hats were common.
Colonel Meriwether Lewis, the founder, envisioned an event that exudes style and sophistication. Like the Epsom Derby, hats and formal attire were required.
Cultural and social significance
Early on, wearing an elaborate hat was a way for women to display their wealth, social status, and panache.
This tradition stuck on, and participants continuously showed up with large, ornate hats. Today, classical and whimsical hats are bold fashion statements that complement derby attire.
Sun protection
Besides aesthetic value, wide-brimmed hats provide shade and protection from Kentucky’s sun.
The derby is mostly an outdoor event, and you risk prolonged exposure to the sun. With your hat on, you needn’t worry about sunburn and sunspots.
Media coverage
The Kentucky Derby is highly anticipated and receives extensive television and media coverage.
Derby fashion takes top billing in the event’s allure, intriguing audiences worldwide. As such, sporting a large, conspicuous hat will make you stand out during the event.
Personal expression
The Kentucky Derby provides a unique opportunity to express your creativity and individuality. Wide-brim hats can accommodate elaborate adornments that match your personal taste.
Types of Hats Suitable for the Kentucky Derby
Fascinators
In recent years, fascinators have gained increased popularity, especially among young attendees.
Fascinators don’t have a crown or brim, distinguishing them from other hats. These whimsical headpieces are worn on one side of the head. To wear, you first need to attach the fascinator to a hair clip, headband, or comb.
Despite their size, fascinators are captivating and strike a balance between function and fashion. You can embellish your fascinator with beads, organza, rhinestones, flowers, or feathers.
Additionally, they’re lightweight and easier to travel with. You can decide to go wild with your fascinator or wear one that matches the rest of your outfit.
Wide-brim hats
The wide-brimmed hat is possibly the most notable Kentucky Derby hat. Renowned for its sun-shielding efficacy, this headwear boasts a 4-inch brim. This provides a surface to attach flowers, netting, bows, and other decorative elements.
Sombreros, Panama hats, fedoras, sun hats, and boaters all include an exaggerated brim. For a sartorial finish, match the hat with a colorful jumpsuit or spring dress.
They are a fashion statement as much as they shade you from the Kentucky sun.
The pillbox hat
For a classic yet whimsical look, the pillbox hat proffers a dash of vintage flair. Pillboxes sit atop the head’s crown and are often unadorned.
Nevertheless, recent designs may include brooches or netting for a more urban look. Although less common than fascinators and wide-brimmed hats, pillbox hats continue to evoke nostalgic fashion trends.
The boater hat
Hat trends at the derby often focus on women, leaving men out of the narrative. Boater hats are a gender-neutral favorite popular among the locals. For a sleek look, pair with seersucker suits and linen blazers.
Typically, a flat-brimmed straw hat comes with an included ribbon. Still, some women decorate their boater hats for a personalized, elegant twist.
How to Choose the Right Derby Hat for You
Choosing the perfect derby hat adds authenticity and sophistication to your outfit. Here are some tips to keep in mind when selecting a Kentucky Derby hat:
Complement your outfit
Your derby hat should match your outfit without competing for attention. For a polished derby look, treat the hat as an extension of your attire and not as an afterthought.
The hat should contrast or complement your outfit’s color palette to make it stand out. A plain-colored hat works well if your outfit features bold patterns.
However, if you’re going for a simple outfit, wear hats with patterns or texture to balance the look.
Your face shape matters
Faces have different shapes, limiting your options to hats that flatter your features. If you’re round-faced, wear a hat with an angular brim and a higher crown to add definition.
For oval faces, you can pull off any hat style, so feel free to explore your choices. Square faces require hats with rounded or floppy brims to soften the edges of the jawline.
Lastly, heart-shaped faces go well with a medium-brim hat to balance out the wider forehead.
Consider the weather
The derby is held in May when it’s typically warm and sunny. This pleasant weather allows you to enjoy the day’s festivities without compromising your look.
Still, a wide-brimmed hat is handy to shade you from the sun’s rays. But if you’re anticipating a windy day, opt for a secure fascinator with a snug fit.
This ensures it stays in place, maintaining your modish look.
Go for bold details
The Kentucky Derby is known for extravagant hats and statement pieces. Don’t hesitate to embellish your hat with feathers, flowers, bows, and sequins.
You don’t want to miss out on this opportunity to display your creativity and fashion sense.
Additionally, opt for bold colors and stunning accessories that complement your overall ensemble.
Prioritise comfort
Your hat should fit snugly and remain comfortable on your head. Nothing ruins Derby Day more than an ill-fitting hat that shifts or falls constantly.
Adjustable hats with elastic inner bands provide the perfect fit. You can also use traditional hatpins to anchor the hat to your hair.
Additionally, the hat should be made of lightweight materials, such as straw, cotton, or sinamay. While breathable fabrics rock in a hot Derby Day, wear a hat with waterproofing features if you’re expecting some rain.
Reflect your personal style
Depending on your taste, pick hats with classic shapes for a timeless finish. If you want to stand out, opt for hats with distinctive shapes and vibrant colors.
Incorporate playful adornments for a whimsical look. For a contemporary twist, sleek hats with subtle embellishments exude a sophisticated elegance.
Style your hair
Your hairstyle impacts how the hat sits on your head. It should complement the hat for increased comfort and elegance.
If you’re sporting a wide-brim hat, consider a low chignon or soft curls to avoid a bulky look under the hat. Don’t overdo it with the hairstyle lest it draw attention away from the hat.
Fascinators and smaller headpieces pair well with a half-up hairstyle, voluminous waves, and an elegant updo.
You’ll need to secure the fascinator with a comb or bobby pins to keep it in place. If your hat sits at an angle, part your hair right for an elegant and balanced look.
However, if your hat is remarkably ostentatious, opt for a sleek, tucked-back hairstyle. This ensures the headpiece remains the focal point.
The Kentucky Derby is an outdoor event, so be sure to come prepared for potential humidity and wind.
In this case, apply anti-frizz and secure the hair with pins to prevent frizzy strands.
If your hair needs extra support, use fancy headbands and decorative pins to secure your look. Adding a touch of hairspray will enhance the outfit, without detracting too far from the headpiece.
Boost your confidence
Your outfit will struggle to make a statement if you don’t back it up with top-tier confidence. Walk gracefully and remember to take lots of pictures.
Insecurities can ruin the fun, regardless of how exquisite your hat is. So, relax and have fun in one of the most sartorial events of the year.
Read also: How to Choose the Best Cowboy Hat Shape.
How to Style Your Kentucky Derby Hat
Here are some styling tips to help you stand out in your derby hat;
Experiment with wild patterns
The Kentucky Derby isn’t a time for subtlety. Try being demure with your outfit or hat choice, and you’ll stick out for the wrong reasons.
Instead, embrace floral prints, gingham, stripes, plaid, and polka dots. These patterns add depth to your look, balancing oversized hat designs.
Embrace bold colors
A vibrant hat can accentuate a simple outfit. You can experiment with bold colors like coral, mint, emerald, and pink.
Ditch the neutral shades for dreamy pastels and vibrant hues. For even bolder self-expression, go for a cap-a-pie monochromatic look in your preferred shade.
Wear comfortable shoes
While the main race lasts for a couple of minutes, the derby is an all-day event. Besides, you’ll spend most of the day standing or walking, which is often strenuous.
Subsequently, ensure that your footwear is comfortable.
Men should be comfortable in loafers and Oxford shoes, while ladies can’t go wrong with block heels, espadrille wedges, or lace pumps. These options remain stylish yet supportive, allowing you to enjoy the event without a care.
Pick alternative headwear
While big hats are trendy when it comes to derby fashion, you can still opt for a more toned-down look.
Opt for a fascinator instead of a full hat if you find it overwhelming. Fascinators deliver elegance while maintaining a minimalist style.
After capturing the moments in a photograph, ditch the wide-brim for something more comfortable. Headbands, bowlers, and pork pie hats are acceptable alternatives for honoring derby traditions.
Go all in with accessories
Your derby attire is incomplete without appropriate accessories. Jewelry, belts, and clutches will complement your hat for a chic look. Pink bow ties and patterned neck ties are not just add-ons; they’re conversation starters. For handbags, sleek purses create a polished finish
Where to Buy Kentucky Derby Hats
You can shop for derby hats online or at a physical store. You can also commission a custom design that meets your preference.
Common derby hat vendors include;
- Local boutiques with exclusive collections
- Churchill Downs gift shop
- Amazon or eBay
Accessories to Pair with Derby Hats
Here are some brilliant accessories that will elevate your derby outfit;
Purses
A fly yet practical purse or clutch pairs well with wide-brims and fascinators. Pick a design that complements rather than overshadows your outfit.
A neutral crossbody bag or small handbag goes well with dresses and jumpsuits. Your purse should include a wristlet or strap to keep your hands free when sipping a mint julep.
Jewelry
Your jewelry should be chic and refined. If you’re wearing an elaborate hat, keep your accessories minimal with dainty bracelets, pearl studs, or a simple necklace.
If your hat screams subtlety, don’t shy away from wearing a statement necklace and earrings.
Shoes
Your shoes should be comfortable yet stylish. The Kentucky Derby is an all-day event, and you’re likely to stand or move about a lot.
We recommend wearing block heels, stylish wedges, and classic pumps to the event. For men, wear dress shoes or loafers to match the derby’s spirit.
Your footwear shouldn’t be overly casual. You can, however, bring a pair of flats with you in case you get sore feet.
Gloves and Scarf
For a classic derby look, add a vintage-style scarf or delicate gloves to enhance your look. Besides being lightweight, your gloves should match your outfit’s color palette.
Sunglasses
Aviator sunglasses are both stylish and provide shade for your eyes. Look for a stylish pair that complements your face shape and enhances the elegance of your outfit.
FAQs
What kind of hat should I wear to the Kentucky Derby?
You can wear a wide-brimmed hat, a classic fedora, a traditional bowler hat, or a fascinator. While wearing hats is optional during the derby, donning one shows that you understand the event and its traditions. Select a headwear that complements your attire and suits your individual style. Ensure the hat is comfortable with a breathable design ideal for Kentucky’s spring weather.
How to pick a Kentucky Derby hat?
When selecting a Kentucky Derby hat, choose one that fits your head correctly in terms of both size and shape. Next, decide on the color palette of your hat. Bright hues and bold colors are typically chosen by guests who want to make a statement. Finally, choose a fascinating hat with details that align with Derby traditions.
Do you have to wear a hat to a Kentucky Derby party?
While hats aren’t a derby staple, they’re steeped in history and are becoming more popular by the day. Additionally, hats are appropriate for men as much as they are for women. Male attendees are encouraged to wear fedoras, straw bowlers, or boater hats to this fashionable event. Women can wear fascinators, cloche hats, and wide-brimmed hats.
Do people wear cowboy hats to the Kentucky Derby?
Yes, derby goers flock to Churchill Downs wearing cowboy hats, fedoras, and Panama hats. As spring arrives, equestrians begin planning for the most anticipated event in Kentucky. The derby is held on the first weekend of May, offering a spectacle of festivities you ought not to miss. Hats are versatile, allowing you to add additional accessories, such as feathers and ribbons.
Why do people wear fancy hats to the Kentucky Derby
In addition to being a horse racing event, the Kentucky Derby doubles as a fashion showcase. Attendees show up with fancy hats in line with the Derby’s spirit and tradition. Hats are statement pieces that display elegance, style, and class. Additionally, wide-brimmed hats offer shade from the scorching sun.
What type of hat is a Derby?
The derby, also known as a bob hat, a coke hat, a billycock, or a bowler hat, features a rounded brim and crown. Bowler hats were conceptualized by London milliner Thomas Bowler, consisting of hard felt. In recent times, derbies have gained much traction among men of high social standing.
What’s the difference between a fedora and a Derby hat?
Fedoras have a flat, wider brim with a teardrop-shaped crown. On the other hand, derby or bowler hats have a rounded crown without indentation. The brim is narrower and curls on the side. Additionally, derby hats lack the distinctive crease at the crown and pinched sides that give fedoras a much sharper look.
Should I wear my hair up or down with a fascinator?
Updos are timeless and pair well with fascinators, delivering a classic look. Wear your hair up to keep it neat and tidy. This style keeps hair out of your face and offers a firm base to attach your fascinator. Ladies should wear their hair up with a large fascinator or a high-necked dress.
What Kind of Hat to Wear to the Kentucky Derby? Conclusion
Kentucky Derby hats are more than just mere accessories. They’re a declaration of style, confidence, and class.
The right headpiece enhances your look, making a lasting and unforgettable impression. Additionally, it speaks of artistry, heritage, and confidence, setting you apart in a sea of splendor.
In the end, the horses may claim the roses, but the hat ensures you claim the moment. Which hat are you rocking to the event?
