The SterlingGypsy

The SterlingGypsy Helping women find their "Cowgirl Style" since 2011
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The Sterling Gypsy is a wild mix of western grit, handmade charm, and modern flair — where custom hats, cowhide, and creativity collide. 🤠✨

Founded by Allysha — fire-branding, accessory-lovin’ mama with a passion for creating one-of-a-kind pieces that tell your story. What started as a way to give her daughters stylish western accessories for 4H has grown into a full-blown custom shop serving up:



🧢 Handcrafted custom hats
🔥 Fire-branded & laser-engraved leather + cowhide goods
💍 Trendy western-inspired jewelry
🎁 Personalized keepsakes made with heart

Whether you’re showin’ out at a rodeo, celebrating something big, or just want something that feels uniquely you — we’ve got something special waiting.

📍Proudly based in Kentucky
📦 Shipping worldwide
📥 DM us to start your custom order!

☀️🇺🇸 SUMMER IS OFFICIALLY HERE! 🇺🇸☀️The countdown to the **4th of July** and the **80th Anniversary of the Blackberry Fe...
06/23/2026

☀️🇺🇸 SUMMER IS OFFICIALLY HERE! 🇺🇸☀️

The countdown to the **4th of July** and the **80th Anniversary of the Blackberry Festival** is on, and we've got everything you need to look cute all summer long! 💜✨

From festival tees and patriotic hats to easy-breezy rompers, accessories, and all the red, white, and blue vibes, we've been busy stocking both locations with fresh arrivals.

Whether you're headed to the lake, a backyard BBQ, fireworks with family, the Blackberry Festival, or just soaking up some Kentucky sunshine, we've got your summer wardrobe covered. ☀️🍦🎆

📍 **Carlisle Location**
116 East Main Street, Carlisle, KY
🕙 Tuesday–Friday 10AM–6PM
🕙 Saturday 10AM–2PM

📍 **Midway Location**
117 East Main Street, Midway, KY
🕚 Tuesday–Saturday 11AM–7PM
🕐 Sunday 1PM–5PM

Stop by, sip something cold, shop new arrivals, and get your summer wardrobe in check! ❤️🤍💙

☀️🇺🇸🛍️💜

❤️🤍💜 The countdown is ON! 💜🤍❤️We're officially counting down the days until the 80th Anniversary of the Annual Blackberr...
06/22/2026

❤️🤍💜 The countdown is ON! 💜🤍❤️

We're officially counting down the days until the 80th Anniversary of the Annual Blackberry Festival—the longest-running festival in Kentucky! 🎉

To celebrate, we've created these exclusive Red, White & Blackberry tees and embroidered hats right here in-house!

Our tees are available on Comfort Colors because they're one of our absolute favorites. If you've never worn one, here's why we love them:

✨ Ultra-soft, lived-in feel from day one
✨ 100% ring-spun cotton for superior comfort
✨ Durable construction that holds up wash after wash
✨ Relaxed fit that's perfect for summer festivals, parades, fireworks, and all your favorite Kentucky traditions
✨ Garment-dyed colors that stay beautiful over time

Not a Comfort Colors fan? No worries! We can make this design on the shirt style you prefer.

💜 Red, White & Blackberry Tees
Youth XS-XL • $20
Adult S-2XL • $25

🧢 Embroidered Cotton Canvas Hats
Available now while supplies last! • $20

🎉 FESTIVAL BUNDLE SPECIAL 🎉
Choose any TWO festival shirts OR a festival shirt and hat bundle for just $40!

Whether you're a lifelong festival-goer or celebrating for the first time, we've got you covered for all the Blackberry Festival fun.

Available in both locations and online!

Happy Father's Day to all the dads, grandpas, stepdads, bonus dads, and father figures out there! 💙Today we're giving a ...
06/21/2026

Happy Father's Day to all the dads, grandpas, stepdads, bonus dads, and father figures out there! 💙

Today we're giving a special shoutout to our very own shop dad, Todd! 🤩

Around here, Todd wears a lot of hats—fix-it guy, crisis manager, heavy lifter, problem solver, professional advice giver, and a second dad to our staff. If something breaks, needs built, moved, repaired, or figured out, Todd is usually the one making it happen.

We are beyond thankful for all the ways he helps keep things running behind the scenes and for always being willing to lend a hand (or a tool 😉).

Help us wish Todd and all the amazing dads out there a very Happy Father's Day! 💙

✨ Happy Friday, y'all! ✨We're open in BOTH locations today and ready for a great weekend! 🛍️☕🍷🎉 25% OFF ALL Men's Appare...
06/19/2026

✨ Happy Friday, y'all! ✨

We're open in BOTH locations today and ready for a great weekend! 🛍️☕🍷

🎉 25% OFF ALL Men's Apparel, Accessories & Gifts for Dad! 🎉

Still need a Father's Day gift? We've got wallets, hats, keychains, apparel, drinkware, and plenty of unique finds Dad will actually use.

📍 Carlisle
116 East Main Street, Carlisle, KY
⏰ 10 AM - 6 PM

📍 Midway
117 East Main Street, Midway, KY
⏰ 11 AM - 7 PM

Stop by, shop local, grab a latte, milkshake, cocktail, or wine slushie, and kick off your weekend with us! ❤️

✨ WE’RE HOME, MIDWAY! ✨The Sterling Gypsy has officially settled into her new home in Midway, and y’all… we are absolute...
06/19/2026

✨ WE’RE HOME, MIDWAY! ✨

The Sterling Gypsy has officially settled into her new home in Midway, and y’all… we are absolutely in love with this space! 🤩

Honestly, it feels like a mini version of our Carlisle location, and if you’ve followed our journey for very long, you know we believe there’s a reason for everything. Looking back now, this move was meant to happen. ❤️

We can’t wait for you to see the charm, the character, the hats, the apparel, the accessories, and all the little details that are making this space feel so perfectly Sterling Gypsy.

📍 117 East Main Street
Midway, KY

🕒 Store Hours:
Tuesday: 11 AM - 7 PM
Wednesday: 11 AM - 7 PM
Thursday: 11 AM - 7 PM
Friday: 11 AM - 7 PM
Saturday: 11 AM - 7 PM
Sunday: 1 PM - 5 PM

Come shop, browse, and help us break in our beautiful new home. We can’t wait to welcome you through the door! 🖤✨

🤠🖤✨

☀️ Happy Hump Day, friends! ☀️Need a little midweek pick-me-up? We've got you covered! 💖📍 Carlisle | 116 E Main Street☕ ...
06/17/2026

☀️ Happy Hump Day, friends! ☀️

Need a little midweek pick-me-up? We've got you covered! 💖

📍 Carlisle | 116 E Main Street
☕ Latte Bar Open 10 AM – 6 PM

🎉 HAPPY HOUR • 4 PM – 6 PM 🎉
🥤 $5 Milkshakes
🍹 $5 Cocktails
☕ $4 Lattes
🍺 $2 Beer

Whether you're craving a caffeine boost, an afternoon treat, or a cocktail after work, we've got the perfect excuse to stop by!

🛍️ And don't forget our Midway location is open today from 11 AM – 7 PM for a little retail therapy! New arrivals, accessories, gifts, custom hats, and all the things you didn't know you needed. 😉

📍 Midway | 127 E Main Street

Grab a friend, treat yourself, and make the middle of the week a little more fun! 💕

☀️ Happy Tuesday, Carlisle!We're open today and ready to help you check Father's Day shopping off your list! Stop by and...
06/16/2026

☀️ Happy Tuesday, Carlisle!

We're open today and ready to help you check Father's Day shopping off your list! Stop by and see Taylor & Sydney and find the perfect gift for Dad before Sunday.

🎁 Father's Day Gift Ideas:
✔️ Custom branded wallets
✔️ Key chains
✔️ Hats
✔️ Apparel
✔️ Custom cowhide gifts
✔️ Personalized accessories
✔️ One-of-a-kind gifts made just for him

Whether he's a cowboy, outdoorsman, farmer, fisherman, or just the hardest-working guy you know, we've got something he'll love.

📍 The Sterling Gypsy – Carlisle
116 East Main Street
🕙 Open Today 10 AM – 6 PM

Father's Day is THIS Sunday... don't wait until the last minute! 🤠

☀️ Monday Check-In! ☀️Let's have a little fun this morning...If your week had a theme song, what would it be? 🎶😂💃 "Man! ...
06/15/2026

☀️ Monday Check-In! ☀️

Let's have a little fun this morning...

If your week had a theme song, what would it be? 🎶😂

💃 "Man! I Feel Like a Woman"
☕ "9 to 5"
🤠 "Save a Horse, Ride a Cowboy"
😴 "The Sound of Silence"
🔥 "Life is a Highway"

Or tell us your own! Drop it in the comments below. 👇

Bonus points if it's the first song that popped into your head this morning! 🎵✨
Ours is in the comments 🫠

☀️ Happy Sunny Sunday! ☀️What a beautiful day to stroll Historic Midway, grab a glass of wine, and do a little shopping....
06/14/2026

☀️ Happy Sunny Sunday! ☀️

What a beautiful day to stroll Historic Midway, grab a glass of wine, and do a little shopping. We have something for everyone! 💛

Our Midway location is open today from **1 PM - 5 PM**, and we'd love to see you! Stop in and browse the latest arrivals, check out our custom hats, and enjoy a relaxing Sunday afternoon with us.

📍 The Sterling Gypsy Midway
127 East Main Street
Midway, KY

Wishing everyone a wonderful end to the weekend. See y'all soon! ✨

☀️ It's shaping up to be a fun Saturday in both of our hometowns!🎶 Midway is hosting Bourbon & Blues tomorrow from 12PM–...
06/12/2026

☀️ It's shaping up to be a fun Saturday in both of our hometowns!

🎶 Midway is hosting Bourbon & Blues tomorrow from 12PM–10PM! Enjoy live music, food vendors, shopping, and all the small-town charm that makes Midway so special. Be sure to stop by and see us while you're out enjoying the festivities!

🚴‍♂️ Over in Carlisle, we'll be welcoming cyclists from all over for the Road to Nationals event! If you're downtown cheering them on, we've added extra tables to our front porch so you can kick back, sip your favorite drink, and soak up a beautiful summer day on Main Street.

Whether you're spending the day in Midway or Carlisle, we'd love to see you!

📍 Midway Location
127 E Main Street
Historic Thoroughbred Theatre
Open 11AM–7PM

📍 Carlisle Location
116 E Main Street
Open 10AM–6PM

Grab a latte, milkshake, cocktail, or a little retail therapy and make a day of it! ☕🍹🛍️

Address

116 East Main Street
Carlisle, KY
40311

Opening Hours

Tuesday 10am - 6pm
Wednesday 10am - 6pm
Thursday 10am - 6pm
Friday 10am - 8pm
Saturday 10am - 3pm

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