Local Spotlight: Southern Sunday

At HeyNeighbor, we believe every small business has a story worth sharing. Our Local Spotlight series highlights the people and passion behind the storefronts, studios, and services that make our neighborhoods special. This month, we’re featuring Southern Sunday, a women’s boutique in Naples bringing approachable style and Southern charm to the local fashion scene.

About the Business

Tell us about your business — what do you do and who do you serve?
Southern Sunday is a ladies’ clothing boutique located in Naples, Florida. We serve women looking for classic casual clothing and resort wear at an accessible price point.

How did you get started, and what inspired you to launch your business?
My family has a history in retail—my great-great-grandfather founded the Smithey’s Department Stores in North Carolina. After working in equestrian retail after college, I decided to take the leap into entrepreneurship and launched Southern Sunday in September 2017.

What’s your favorite part about running your business in this community?
I love the sense of camaraderie and support here in Naples. I’ve never experienced a place where women come together so easily and readily to support local businesses.

The Local

What makes your business unique in your neighborhood?
Southern Sunday offers great pieces for everyday wear across a variety of age groups. From classic casual styles to resort-inspired looks, our selections are wearable, approachable, and sustainable.

How do you stay connected with the local community?
I’m a member of various networking groups, participate in pop-up events, and host events in my shop space.

What local partnerships or collaborations have been meaningful to you?
I’ve loved hosting other small businesses in my shop for collaborative events. We’ve had flower bouquet arranging, a wine and dessert pairing class, and a textured art experience. It’s rewarding to work with fellow small business owners, and I enjoy seeing our customers have a great time. I also love hosting sip-and-shop benefits for local schools and nonprofits.

Challenges & Wins

What has been one of your biggest challenges, and how did you overcome it?
Fashion is fast-moving, and it’s easy to chase trends. I’ve had to train myself to stick to our brand voice and stay true to our identity. Honing in on what makes Southern Sunday special—and staying committed to that—has been both a personal and professional win.

What moment or milestone are you most proud of?
I’m proud of Southern Sunday being featured in two fashion shows at the end of the 2025 season—one at Gallery One on Fifth Avenue and the other at the Ladies Power Lunch. We were also named a finalist for Gulfshore Life’s “Best Of” in women’s apparel.

Marketing & Growth

How have you used local advertising (like HeyNeighbor) to grow your business?
To be honest, most of my local advertising has been through events and social media collaborations—so I’m excited to see what HeyNeighbor can do for Southern Sunday!

What’s one marketing tip you’d give to another small business owner?
Don’t be shy about promoting your business! People need to see something at least seven times for it to stick, so be consistent and stay visible. Also, focus on what’s working for your business rather than trying every single marketing method. There’s no one-size-fits-all approach—invest your energy in the areas that give you the best return.

Just for Fun

What’s your go-to lunch spot or coffee place around here?
For lunch, I love Food & Thought 2 or Slicer’s. I’m not a big coffee drinker, but I enjoy Kaleidoscope or Bad Ass Coffee for a refreshing drink and a good place to work.

If your business had a theme song, what would it be?
I play K-LOVE Christian radio in the shop every day, so our theme song would be whatever’s at the top of that station’s chart!

Any funny or surprising story from working with local customers?
Nothing too surprising, but I always smile when I see customers wearing Southern Sunday around town. It brings me so much joy to see them enjoying what they’ve purchased.

Looking Ahead

What’s next for your business — any exciting plans or projects coming up?
I have several exciting events and collaborations in the works as we move into the fall and gear up for the season. I can’t reveal all the details just yet, but they’ll be a fun way to stay connected with the community.

How can people best support you right now?
Spread the word!

Supporting local businesses starts with getting to know the people behind them. At HeyNeighbor, we’re proud to celebrate the entrepreneurs who shape our communities through hard work, creativity, and connection. Know a local business owner whose story deserves the spotlight? Nominate them here and help us share more of what makes our neighborhoods shine.