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One lucky winner will receive a fully styled outfit every month for 12 months, curated by The Sterling Gypsy.
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The Sterling Gypsy
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  • Home
  • The Farmhouse Edit
  • Hats
  • Run for the Roses: Race Day Edit
  • Apparel
  • Blue Skies & Backroads Collection ☀️🛻
  • Jewelry
  • Home Decor
  • Furry Friends
  • Custom Branded Cowhide & Leather
  • The Carry-All Cowgirl Purses and Totes
  • Self Care Collection
Run for the Roses

Run for the Roses

Collection Description:
This collection is straight Derby royalty. The Run for the Roses Collection is all about bold brims, dramatic bows, feathered flair, and head-turnin’ details made for the most fashionable two minutes in sports. Think classic Southern elegance with a modern twist—hats that don’t whisper, they announce.

From soft neutrals to statement silhouettes, every piece is made to stand out trackside, toast mint juleps in style, and have folks askin’ “where’d you get that?” Whether you’re headed to Churchill Downs, a Derby party, or just dressin’ like you should be photographed, these hats bring grace, confidence, and a little Kentucky sass to every outfit.

Long story short: if you ain’t gettin’ stared at, you picked the wrong hat. 💋🌹

Home DecorSelf Care Collection
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The Pink Lily Estate
Regular price $165.00
1 in stock
Quick buy
The Lavender Reserve
Regular price $48.00
1 in stock
Quick buy
The Bluegrass Heiress
Regular price $160.00
1 in stock
Quick buy
Pearls on the Rail
Regular price $98.00
1 in stock
Quick buy
The Black Tie at Churchill
Regular price $196.00
1 in stock
Quick buy
The Golden Filly
Regular price $160.00
1 in stock
Quick buy
Lillies and Lace
Regular price $164.00
1 in stock
Quick buy
Run for the Roses Royale
Regular price $150.00
1 in stock
Quick buy
Silver Cup Socialite
Regular price $150.00
1 in stock
Quick buy
Run for the Lillies
Regular price $160.00
1 in stock
Quick buy
Derby Daydream in Blue
Regular price $95.00

Contact us

About Us

Welcome to The Sterling Gypsy, where western style, small-town heart, and handcrafted magic all meet under one roof. Born right here in the horse capital of the world, our shop started with a mama making western accessories for her daughter — and grew into a full-on boutique experience that folks travel for.

We specialize in custom cowboy hats, cowhide branding, handmade accessories, western apparel, trucker hats, jewelry, and one-of-a-kind gifts you won’t find anywhere else. Whether you’re here to design your dream hat, shop unique western pieces, grab a latte or cocktail, or just soak up the vibe — you’re part of the family the moment you walk in.

Everything we create is made with grit, heart, and a whole lot of Gypsy charm.
We’re a little modern, a little wild west, and proudly rooted in Kentucky soil.

Shop small, stay awhile, and let us help you find something that feels like you.
Because around here, it’s more than shopping —
it’s an experience.

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