Hat or Dress First? The Ultimate Kentucky Derby Style Debate

In the world of high-stakes race day fashion, one question always sparks debate: Do you pick the hat or the dress first?
At an event like Kentucky Derby, where statement headwear is practically mandatory, your choice can make or break your look. Some swear by selecting the perfect dress first, letting the hat be the finishing touch. Others argue that the hat leads the way, dictating the outfit from the top down.
So which strategy wins? Let’s break it down and make sure you walk into Churchill Downs looking flawlessly put together—no matter which approach you take.

1. The Case for Picking the Hat First
Some say the hat is the real star of any Kentucky Derby outfit, and honestly, they might be right.
If you want to make a high-impact fashion statement, your headwear should be front and center.

Why Start with the Hat?
✔ A Bold Hat Sets the Tone – A dramatic wide-brim hat, sculptural fascinator, or custom-designed headpiece can instantly define your look.
✔ Limited Availability – High-end, one-of-a-kind hats sell out fast. If you wait too long, you might end up with a dress that outshines a mediocre hat—which is not the move.
✔ Easier to Match a Dress to a Hat – Finding a dress that complements a bold, well-designed hat is easier than the other way around.

When to Prioritize the Hat:
- If you’re going custom – Commissioning a milliner to create a one-of-a-kind piece? Start here. Your outfit should follow the hat’s lead.
- If you want a standout, statement look – If the goal is fashion-forward drama, the hat
dictates the entire aesthetic.
- If your event wardrobe is neutral-heavy – Own plenty of chic, solid-colored dresses? A standout hat can transform them.
- Pro Tip: If you find a hat you love but it doesn’t match your dress perfectly, pull from the hat’s colors for accessories to tie it all together.

2. The Case for Picking the Dress First
If you’re more outfit-driven, you might want to secure the dress first and let the hat follow. After all, your dress is the foundation of the look—it defines the silhouette, color palette, and overall style.

Why Start with the Dress?
✔ More Dress Options – Unlike hats, dresses come in a wider variety of sizes, styles, and price points, giving you more flexibility.
✔ Fit First, Statement Second – A well-tailored, flattering dress is non-negotiable. A hat is important, but an ill-fitting dress? That’s a disaster.
✔ Color Coordination is Easier – Once you’ve nailed down your base color and style, finding
a hat that enhances (rather than competes with) the look becomes effortless.
When to Prioritize the Dress:
- If you have a specific style in mind – Love a structured midi dress or a sleek jumpsuit?
Get that first, then accessorize.
- If you’re drawn to bold prints or colors – If your dress is already a statement (think
florals, geometric prints, or dramatic silhouettes), your hat should complement, not clash.

- If you need a more tailored fit – Custom alterations take time. If fit is your priority, secure the dress first.
- Pro Tip: If you find a dress you love but the matching hat isn’t available, look for a
neutral or metallic headpiece—gold, silver, and black work with nearly everything.

3. The Power Move: Buy Both Together
For the fashion perfectionists, there’s a third option: shopping for your hat and dress at the same time. This method takes more effort, but guarantees a seamless, editorial worthy look.
How to Shop for Both Simultaneously:
1️⃣ Start with Inspiration – Browse fashion week photos, past Kentucky Oaks looks, and
boutique collections.
2️⃣ Try on Multiple Combinations – If possible, visit boutiques that specialize in both
dresses and millinery to experiment with pairings in real time.

3️⃣ Consider Texture & Material – A structured hat pairs well with a structured dress, while a flowy hat works with softer fabrics.
4️⃣ Use Color Theory – Instead of an exact match, try complementary shades for a high-
end, styled effect.
- Pro Tip: If you’re shopping online, buy from stores with solid return policies so you can swap pieces as needed.

4. What the Experts Say: Hat First or Dress First?
- Hat Designers: Most milliners argue you should start with the hat, especially if you’re
investing in a custom, handcrafted piece. A great hat can’t just be an afterthought.
- Fashion Stylists: Stylists often recommend choosing the dress first, ensuring it flatters your body and feels right before selecting accessories.
- Race Day Regulars: The most seasoned Kentucky Oaks attendees? They buy both together, plan months ahead, and tailor every detail.

5. Final Verdict: Which Should You Pick First?
- If you want a bold, high-impact look: Pick the hat first and let it dictate the outfit.
- If you prioritize fit and comfort: Pick the dress first, then find a hat that complements it.
- If you’re aiming for perfection: Shop for both simultaneously, ensuring a head-to-toe
flawless aesthetic.
At the end of the day, there’s no wrong choice—only a right way to style it. Whether you’re a
hat-first maximalist or a dress-first minimalist, what matters most is that your final look feels
intentional, sophisticated, and undeniably chic.

So—hat first or dress first? What’s your move? Drop your thoughts in the comments.