The SterlingGypsy

09/01/2026

September sippin’ just got a whole lot better. 🍂☕️

We’re officially trading summer flavors for ALLLL the cozy fall goodness. 🤎

Our September menus are loaded with brand-new milkshakes, fall lattes and cocktails — plus our new Fall Y’all Rum Punch Buckets made for sharing… or not. We won’t judge!😂

Come find your new fall obsession at The Sterling Gypsy!

Now we gotta know… which one catches your eye FIRST?! 👀👇🏼Tell us in the comments because we’re taking bets on which one becomes September’s favorite. 🍂

09/01/2026

Starting September off STRONG with this one!😻

THIS is how you mix western with a little wild side. 🐆🤠

A graphic tee + leopard maxi skirt should not go this hard… but HERE WE ARE.

We love an outfit that’s a little unexpected — because basic just ain’t our department. 😉

Shop the whole fit at The Sterling Gypsy!

08/30/2026

The always beautiful megan_anderson915 and our are favorite new tee collection 🤎✨

These aren’t just cute graphic tees — each one carries a little something extra.

Hidden along the hem of every tee, you’ll find an inspirational quote or Bible verse thoughtfully chosen to be your own personal reminder of encouragement, hope, strength, and faith.

A reminder you can carry with you throughout your day. On the good days. On the hard days. And on all the ordinary days in between. 🤍

Sometimes the words we need most don’t have to be seen by everyone else — they’re simply there for you.

Pair them with your favorite denim, layer them under a jacket, dress them up, wear them oversized… but most importantly, wear the message with you. ✨

Cute on the outside. Encouragement tucked inside.

Come see the new collection and find the tee — and the message — that speaks to you. 🫶

08/29/2026

FALL IS ROLLIN’ IN 🍂🤠

And y’all… we have a TON of new fall apparel hitting the floor! From the cutest barn jackets and sweater vests to easy transition pieces, dresses and all the layers you’re gonna want when Kentucky finally decides it’s fall. 😂

Come spend your Saturday with us at BOTH locations!

🤎 CARLISLE
📍 116 E. Main Street, Carlisle, KY
⏰ Open today 10 AM–2 PM

🩷 MIDWAY
📍 117 East Main Street, Midway, KY
⏰ Open today 11 AM–10 PM

And Midway is THE place to be today!

✨ REIMAGINED MARKET
Starting at 10 AM in the courtyard! We’ve got a Sterling Gypsy tent set up with lots of reimagined goodies, one-of-a-kind finds + a few fun extras 👀

🎶 MIDWAY BLOCK PARTY
6–10 PM TONIGHT!

Shop the market, stroll downtown, grab something to eat, come shop all our new fall arrivals, then stick around for the Block Party tonight.

Basically… clear your Saturday. Midway understood the assignment. 🤠🍂✨

Come see us in Carlisle OR make a whole dang day of it in Midway! 🩷

08/26/2026

🚨 CONSUELA IS HERE!!! 🚨

Y’all… we have been WAITING for this one. 😍🌈✨ And she is even prettier in person!

Our first shipment of Consuela has officially landed at The Sterling Gypsy, and we are SO excited for y’all to see what we’ve received so far! Handbags, crossbodies, wallets, accessories and all that colorful Consuela goodness. 💕 And yep… we’re already obsessed.

We’re kicking things off with a TWO-DAY CONSUELA TRUNK SHOW at our CARLISLE location! 🎉

Come shop the collection, try on your favorites and snag the one that’s calling your name before we pack it all up and hit the road!

📍 Carlisle — Wednesday + Thursday
👜 Consuela Trunk Show

Then on FRIDAY, Consuela is headed to MIDWAY for a BIG weekend! 🙌

Midway is gonna be THE place to be with:
✨ Reimagined Market
✨ Midway Block Party on Saturday
✨ Shopping, food, music & all the small-town goodness

And now… a whole lotta CONSUELA. 🌈🤠

Come see what all the fuss is about — because these bags are definitely not made for blending in. And neither are we. 😉

📍 The Sterling Gypsy
Carlisle + Midway, Kentucky

08/25/2026

Life without her will never be the same 🦋

Love is like a butterfly
As soft and gentle as a sigh 🎶🦋

08/24/2026

🤠✨ WE’RE REIMAGINING WESTERN! ✨🤠

We are SO excited for Midway’s Reimagined Market this Saturday, August 29th! We’ll be there ALL DAY from 11AM–10PM in the Downtown Midway Courtyard—and we’ve been working on something extra special for you. 🐎🌵

For this market, we’re creating our very own “REIMAGINED” WESTERN BOOTH… and we seriously cannot wait for you to see it! 👀✨

We’ve been taking pieces, ideas, and western favorites and giving them a whole new life. Think western charm, one-of-a-kind finds, unexpected details, repurposed treasures, and pieces that have been completely REIMAGINED. 🤎

This market is all about celebrating the art of repurposing • refurbishing • reviving, so of course we had to put our own western spin on it!

Come spend your Saturday in Midway, shop our booth, explore all the amazing vendors, and see what we’ve been busy “reimagining.” 😉

🌵 Midway’s Reimagined Market
📅 Saturday, August 29th
⏰ 11AM–10PM
📍 Downtown Midway Courtyard

And don’t head home too early—the Midway Block Party kicks off at 7PM with live music from Five Below Band! 🎶✨

Grab your friends, throw on your favorite western outfit, and make a day of it. We have SO many fun things planned for our booth and we can’t wait for you to see what we’ve REIMAGINED! 🤠🪩🌵

SEE YOU SATURDAY, MIDWAY! 🤎

08/23/2026

Happy Sunday, y’all! ☀️🤠

It’s gonna be a BEAUTIFUL day in Midway, and we’re open **12–5 today!**

Grab some lunch in historic downtown Midway, stroll around town, then come shop with us! 🛍️ We’ve got new arrivals, fall favorites, game day goodies, hats, accessories & plenty more waiting on ya.

Good food + cute shops + a sunny Sunday in Midway? That’s hard to beat. 💙

📍 The Sterling Gypsy — Midway
⏰ Open today 12–5

Come make a day of it! ✨

08/22/2026

WESTERN MEETS COMFORT 🤠👖✨

Our NEW Judy Blues just landed and y’all… YES PLEASE.

Western-inspired details + that famous Judy Blue stretch + TUMMY CONTROL = the jeans we’ll be living in all fall. 🙌

These are made for real women, real curves, and real life — comfy enough to wear all day but cute enough to make the whole outfit.

Pair ’em with your favorite boots, a graphic tee, or throw on a cute sweater

Come try them on and see what the Judy Blue hype is all about!

Available now online and at The Sterling Gypsy 🤎

Open today 10-2 in Carlisle & 11-7 in Midway!

08/22/2026

Okay all my fellow pickers… we’ve been MAKING something new at The Sterling Gypsy and you are going to LOVE these! 😍

Introducing our NEW handmade Picky Pads!

These little sensory pads are filled with beads tucked inside soft silicone for the most satisfying picking experience. They’re perfect for keeping busy hands occupied and for a little calming, stress-relieving downtime.

But here’s the BEST part…

♻️ THEY’RE REMELTABLE!

Once you’ve picked all the beads out, save everything! Put the silicone back into the included silicone mold, remelt it, add your beads back in and make your Picky Pad all over again.

Pick it. Melt it. Refill it. Repeat. 🙌

We’re making these ourselves in all kinds of fun bead mixes, and honestly, making them might be almost as satisfying as picking them. 😂

⚠️ Contains small beads and small parts. Recommended for ages 6+. Not intended for children under 3 due to choking hazard. Adult supervision recommended for children.

Coming soon to The Sterling Gypsy! 🤎

Okay, be honest… who’s a picker?! 🙋‍♀️