Hat or Dress First? How to Plan the Perfect Kentucky Derby Outfit

 

Have you ever stood in front of your closet, wondering if you should pick your hat or your dress first for a big event? If you’re getting ready for the Kentucky Derby, this question pops up every year, and the answer can make a huge difference in how you look and feel on the race day.

Let’s talk about what really matters: making sure you look amazing and feel confident. This guide will help you plan your outfit step by step. No matter your style, you’ll find tips and ideas that are perfect and fit your needs.

Hat or Dress First?

Some people swear by picking the perfect dress and then finding a hat that matches. Others believe the hat should come first, setting the tone for the whole outfit. So, which is the best way to go?

Here’s the truth: both methods work, but the choice depends on what you care about most. If you want to stand out and make a statement, your hat might be the star. If comfort and fit are your top priorities, your dress should come first.

Why Some People Start with the Hat

For many, the Kentucky Derby is all about the custom hats or the bold derby hats for women that steal the spotlight and show off your style. Here’s why starting with the hat makes sense for some:

• A bold hat sets the mood: If you choose a dramatic, wide-brimmed hat or a boldly shaped fascinator your whole look changes instantly.
• Hats for women at the Derby are unique: Many are handmade or custom-designed, so you might not find another one like yours.
• It’s easier to match a dress to a great hat: Once you have a standout hat, you can pick a dress in a color or style that brings out its best features.

If you’re thinking about a custom hat or a one-of-a-kind piece, it’s smart to start with the hat. That way, you can build your outfit around it. If you already have lots of simple, solid-colored dresses, a bold hat can make them look new and exciting.

Pro tip: If your hat and dress don’t match perfectly, use accessories like shoes, jewelry, or a clutch to tie them together. Pick colors from the hat for your accessories, and you’ll look stylish and perfectly dressed for the occasion.

Why Others Start with the Dress

Not everyone wants the hat to be the center of attention. If you love fashion and want your outfit to highlight your best features, you might want to pick your dress first. Here’s why:

• Dresses come in more sizes and styles: You have more options to choose from, so it’s easier to find something that fits just right.
• Color coordination is easier: Once you have your dress, you can look for a hat that matches or complements it.

If you have a specific style in mind, like a midi dress or a jumpsuit, start with the dress. If your dress has bold prints or bright colors, find a hat that makes it look even better, not one that fights for attention.

Pro tip: If you find a dress you love but can’t find a matching hat, go for a neutral or metallic headpiece. Gold, silver, or black hats work with almost any dress.

The Best of Both Worlds: Shopping Together

If you want your outfit to look perfect from head to toe, you might want to shop for your hat and dress at the same time. This takes a little more effort, but the results are worth it.

Here’s how to do it:

• Get inspired: Look at photos from past Derby events or check out what people wore at the Kentucky Oaks for ideas.
• Think about texture and material: A structured hat looks great with a structured dress, while a flowy hat pairs well with softer fabrics.
• Use color theory: Instead of matching everything exactly, try complementary colors for a stylish, high-end look.

What Do the Experts Say?

• Hat designers: They usually say to start with the hat, especially if it’s custom or handmade. A great hat can’t be an afterthought.
• Fashion stylists: They often recommend picking the dress first, so you can make sure it fits your body perfectly before adding accessories.
• Race day regulars: According to them the best outfits come from planning both the hat and dress together, months in advance.

The Final Answer: Which Should You Pick First?

Here’s the simple answer:

• If you want a bold, high-impact look: Pick the hat first and let it set the tone for your outfit.
• If you care most about fit and comfort: Pick the dress first, then find a hat that matches.
• If you want everything to be perfect: Shop for both at the same time, so you can see how they look together.

There’s no wrong way to do it, just make sure your final look feels intentional and stylish. Whether you’re a hat-first person or a dress-first person, the most important thing is that you feel confident and happy with your choice.

Tips for Choosing the Right Kentucky Derby Outfit

Now that you know how to start, here are some extra tips to make sure your outfit is perfect for the Derby:

• Comfort is key: You’ll be wearing your hat and dress all day, so make sure they feel good.
• Choose shoes you can walk in: The Derby is a big event, and you’ll be on your feet a lot.
• Be yourself: Don’t worry about dressing, pick an outfit that shows off your personality.

If you want more ideas for what to wear at big events like this, you might find inspiration from other guides on what to wear at the Kentucky Oaks, or from the latest hat trends and styles.

Common Questions About Kentucky Derby Outfits

Here are some of the most common questions people have when planning their Derby look:

Q. Should I wear a big hat or a small one?

A. Both are great! Big hats make a statement, but small fascinators are stylish and easy to wear. Pick what feels best for you.

Q. How do I know if my hat and dress match?

A. Look at the colors and styles. If your dress is bold, choose a hat that complements it. If your hat is the star, pick a dress that lets it shine.

Q. Can I wear a jumpsuit instead of a dress?

A. Absolutely! Jumpsuits are stylish and comfortable, and they look great with the right hat.

Q. What if I can’t find a matching hat?

A. Try a neutral or metallic hat. Gold, silver, or black hats go with almost anything.

Q. How do I keep my hat on all day?

A. Use hat pins or bobby pins to secure it. Make sure it’s comfortable before you leave the house.

Q. What colors are best for the Derby?

A. Bright colors, pastels, and florals are always popular. Have fun and pick something you love.

What to Avoid When Planning Your Outfit

Even with the best planning, some things can go wrong. Here’s what to watch out for:

• Don’t pick uncomfortable shoes: You’ll be walking a lot, so comfort is important.
• Don’t forget about the weather: Check the forecast and plan accordingly.
• Don’t wear a hat that’s too heavy: You’ll be wearing it all day, so make sure it’s light and comfortable.
• Don’t worry about following trends: The best outfits are the ones that make you feel good.

The Secret to a Perfect Kentucky Derby Outfit

The secret is simple: plan ahead, pick pieces you love, and make sure you feel comfortable and confident. Whether you start with the hat or the dress, the most important thing is that you enjoy your look and have fun.

If you want to see more ideas or find the perfect hat or dress, check out The Hat Girls for a wide selection of Kentucky derby hats for women.

Real-Life Scenarios

Imagine this: you’re getting ready for the Derby and you find a beautiful custom hat that you absolutely love. You decide to build your outfit around it, picking a dress and accessories that make it stand out. Or maybe you find a dress that fits you perfectly and makes you feel amazing. You choose a hat that matches and completes your look.

Either way, you’ll look and feel great. The key is to pick pieces that make you happy and confident.

Final Thoughts

Planning your Kentucky Derby outfit should be fun, not stressful. Whether you start with the hat or the dress, the most important thing is that you feel good about your choice. Take your time, try different combinations, and don’t be afraid to show off your style.

If you’re looking for more inspiration or want to see the latest trends, check out our guides on what to wear at the Kentucky Oaks and the top hat trends for this season.

Why Trust Matters

When you’re planning a special outfit, you want advice that you can trust. That’s why it’s important to get tips from people who know what they’re talking about. At The Hat Girls, we’re here to help you find the perfect look for any occasion. 

Make Your Derby Day Look One to Remember

Visit The Hat Girls to browse our collection of hats for women, Kentucky derby hats, and custom hats. If you want something bold or classic, we have options for every style and budget. 

Let us help you create an outfit that’s as unique as you are.