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!

☀️ 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! ☕🍹🛍️

🍹✨ LAST CALL FOR LLC TONIGHT! ✨🍹We've still got a few spots left for Ladies Love Cocktails tonight, and we'd love for yo...
06/11/2026

🍹✨ LAST CALL FOR LLC TONIGHT! ✨🍹

We've still got a few spots left for Ladies Love Cocktails tonight, and we'd love for you to join us!

For just $20, you'll enjoy:
🍸 4 drink tastings
🧀 Food & snacks
😂 Plenty of laughs
💕 Great company
🥂 A fun night out with the girls

Whether you're coming with friends or flying solo, there's always a seat at our table. Grab your spot and come hang out with us tonight!

📍 The Sterling Gypsy – Carlisle
🕡 6:30 PM - 8:30 PM

Message us to reserve your seat before they're gone!

New !!💖🎀Simply Southern Youth Tees
06/10/2026

New !!
💖🎀Simply Southern Youth Tees

🇺🇸🧢 NEW HATS HAVE ARRIVED! 🧢🇺🇸We're obsessed with these new patriotic trucker hats that just landed at The Sterling Gyps...
06/10/2026

🇺🇸🧢 NEW HATS HAVE ARRIVED! 🧢🇺🇸

We're obsessed with these new patriotic trucker hats that just landed at The Sterling Gypsy! ❤️🤍💙

✨ Bad Day to Be a Hotdog
✨ Oh My Stars
✨ Patriotic Flag

These custom designs were created just for us by my talented sister-in-law over at Midway Embroidery, and they are the perfect finishing touch for all your summer plans, Fourth of July celebrations, Blackberry Festival fun, lake days, concerts, and backyard cookouts!

💥 Only $15 each

🛍 Available in both locations and online while supplies last!

📍Carlisle
116 E Main Street
Tuesday-Friday 10-6
Saturday 10-2

📍Midway
127 E Main Street
Wednesday-Saturday 11-7
Sunday 1-5

Which one is your favorite? Drop a ❤️ for Hotdog, ⭐ for Oh My Stars, or 🇺🇸 for the Flag Hat!

🍹✨ LLC is THIS THURSDAY! ✨🍹Ladies, grab your girlfriends and join us for another fun-filled Ladies Love Cocktails night ...
06/09/2026

🍹✨ LLC is THIS THURSDAY! ✨🍹

Ladies, grab your girlfriends and join us for another fun-filled Ladies Love Cocktails night this Thursday from **6:30 PM – 8:30 PM** at The Sterling Gypsy in Carlisle!

We'll have drinks, snacks, laughs, and plenty of girl time. 💕 Seating is limited, so be sure to reserve your spot by commenting below or sending us a message!

And while you're making plans for Thursday, stop by and see us today! 🛍️

📍 Carlisle Location
116 E. Main Street
Carlisle, KY

⏰ Open Today 10 AM – 6 PM

We can't wait to see y'all! 🩷

Happy Sunday, friends! ☀️We're open today in Midway from 1 PM–5 PM, so stop by and see Samantha and do a little Sunday s...
06/07/2026

Happy Sunday, friends! ☀️

We're open today in Midway from 1 PM–5 PM, so stop by and see Samantha and do a little Sunday shopping! 🛍️

We’ve restocked one of your favorites — our Loves Jesus tee! ✨ This beautiful design is created locally by Doodles by Rebecca in Georgetown, Kentucky, and we couldn't be happier to have her designs back in the shop.

Rebecca's tees are always top-notch quality, thoughtfully designed, and full of charm. We love supporting fellow small business owners, and when you purchase one of these tees, you're supporting not just one, but TWO Kentucky small businesses. ❤️

Come grab yours before they're gone again and check out all the new arrivals while you're here!

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

🕐 Open Today: 1 PM–5 PM

🌾✨ Headed to Railbird in style! ✨🌾One of our favorite custom hats from yesterday's Hat Bar in Midway. This beauty starte...
06/06/2026

🌾✨ Headed to Railbird in style! ✨🌾
One of our favorite custom hats from yesterday's Hat Bar in Midway. This beauty started with a classic ivory hat and came to life with delicate vintage lace, soft pearl accents, a hand-selected vintage pin, and custom branding.
And can we talk about that vintage brooch? Absolute chef's kiss. 🤌🤍 Paired with the pearl hat band, it gives the perfect mix of western charm, vintage romance, and festival-ready flair.
Whether you're headed to Railbird, a summer concert, the races, or just looking for a one-of-a-kind statement piece, our Hat Bar lets you create something that's uniquely yours.
📍 Midway & Carlisle Locations
✨ Walk in and create your own custom hat
🤠 No appointment necessary

🐄🍀 SHOW SEASON IS HERE! 🍀🐄How adorable are these new "Show Season" Comfort Colors tees?! Featuring all the livestock sho...
06/05/2026

🐄🍀 SHOW SEASON IS HERE! 🍀🐄
How adorable are these new "Show Season" Comfort Colors tees?! Featuring all the livestock show favorites in a fun checkerboard design, these are perfect for fair season, jackpot shows, livestock judging, barn days, and cheering on your favorite showman from the stands!
✨ Available in:
• Youth XS – XL
• Adult Small – 3X
📍 Available NOW at BOTH Sterling Gypsy locations!
🤠 Carlisle Location
116 East Main Street
Carlisle, KY
Tuesday–Friday: 10 AM – 6 PM
Saturday: 10 AM – 2 PM
🤠 Midway Location
127 East Main Street
Midway, KY
Wednesday–Saturday: 11 AM – 7 PM
Sunday: 1 PM – 5 PM
Grab yours before your next show weekend and represent your livestock-loving lifestyle in comfort and style! 🐖🐐🐄🐑🍀
🛍 Also available online at The Sterling Gypsy!

✨ More New Arrivals Have Hit the Floor! ✨Y'all... the boxes just keep showing up and we're not mad about it! 😍 From cute...
06/04/2026

✨ More New Arrivals Have Hit the Floor! ✨

Y'all... the boxes just keep showing up and we're not mad about it! 😍 From cute summer outfits and accessories to boutique favorites you'll be reaching for all season long, we've got something new waiting for you.

MYSTERY GLITTER DUMPLINGS RESTOCKED!!

Grab your bestie, take a little shopping break, and come see what's new in store today! 💕

📍 Carlisle Location
116 East Main Street, Carlisle, KY
⏰ Open Today: 10 AM - 6 PM

📍 Midway Location
127 East Main Street, Midway, KY
⏰ Open Today: 11 AM - 7 PM

Can't make it in? Shop online anytime at thesterlinggypsy.com 🛍️

We can't wait to see y'all today! 💖

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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