Spring in Louisville means one thing: the Kentucky Derby. Equal parts sport, spectacle, and social scene, it’s as much about what you wear as where you place your bets.

We asked our own team member Sarah Bonifant, our unofficial Derby expert, to share exactly what she packs, wears, and swears by for a seamless (and chic) race day.

Sarah wears the Sabrina Midi Dress from Spring 2026

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First Things First: The Outfit

The Derby is not the moment for minimalism.

Think bold prints, feminine silhouettes, and a hat that does most of the talking.

Sarah’s rule: “If it feels like too much, it’s probably just right.”

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Shoes That Won’t Sink 

Churchill Downs is grass-heavy, translation: stilettos are a liability.

What to wear instead:

Platform heels

Block heels

Wedges

"You’ll be walking on turf all day. A thicker heel is non-negotiable.”

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The Bag: Small, Strategic, Chic

Bag rules matter here.

Keep it petite (a clutch is safest)

If you go bigger, opt for a clear bag to meet venue guidelines

A statement clutch is the easiest way to finish the look.

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Accessories That Actually Matter

This is where experience shows.

Sarah’s must-haves:

Handheld fan (equal parts practical and chic)

Extra bobby pins (wind happens)

Mints (you’ll be chitchatting all day)

Mini perfume + lip gloss (quick refresh moments)

Parasol or umbrella (sun or surprise rain)

Light poncho (just in case)

“You’re outside all day—comfort and polish go hand in hand.”

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Don’t Skip the Traditions

Some things are non-negotiable.

Order the Mint Julep - preferably in the iconic pewter cup

Lean into the pageantry (this is not a low-key event)

“It’s part of the experience. You have to.”

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The Unexpected Finishing Touch

If there’s one wildcard to add:

Funky sunglasses.

"They’re not just an accessory, they’re a conversation starter."

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Shop Sarah's Picks: 

Shop the Sampaguita Earrings with Sabrina Midi Dress in ivory and pink

Shop the Manila Lace Midi Dress and Esperanza Midi Dress

Shop the Brooklyn Mini Dress, Preston Convertible™ Earrings, Elliana Mini Dress, Sampaguita Earrings in Silver, and Rafe x Mestiza Solihiya Clutch Bag

Shop the Georgiana Gown and Nereida Gown with the Sampaguita Earrings