Charming boutique storefront with open doors, striped pillows on wooden benches, and warm lights illuminating the entrance.

Apparel & Accessories Gifts & Housewares Personalization

Headley Hat Co

Headley Hat Co, formerly part of the Pop-Up District, is proud to welcome customers to their new storefront in Seaside’s Four Corners. Browse from a wide selection of men’s and women’s hats and make them your own at their custom hat bar with branding, hand-stitching, charms, ribbons, and more. You’ll also find a wide selection of Tecovas western boots, custom trucker hats, and a curated collection of home goods. Visit them everyday from 10am to 7pm.

Website

https://www.headleyhat.com/

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Stylish hat boutique interior with illuminated “Headley Hat Co” sign, neatly displayed hats, and mirror.

Shelf displays Ralph Lauren book, three white candles in black box, bracelet, and cowboy photograph in frame.

Shelves stacked with neatly arranged wide-brim hats in various colors and styles.

Charming boutique storefront with open doors, striped pillows on wooden benches, and warm lights illuminating the entrance.

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For generations, love stories have unfolded here.

For generations, love stories have unfolded here.

From intimate ceremonies on the beach to joyful celebrations on the Lyceum Lawn, weddings in SEASIDE® have always carried a certain kind of romance that is timeless, personal, and rooted in place.

Over the years, we’ve witnessed vows exchanged, first dances, and families gathered from near and far. Each wedding feels different, yet each belongs here.

If you’re dreaming of beginning your next chapter in #SeasideFL, comment WEDDINGS for more information. 🤍

A new addition to our beloved Post Office. 🇺🇸

Our community gathered this morning to dedicate our new flagpole, a detail imagined and thoughtfully brought to life by our team and the Davis family. To honor both our past and our future, the area was intentionally designed to reflect the original flagpole that once stood at the Post Office.

Our community is built on intention, and even the smallest additions carry meaning to us. This one rises with gratitude, for tradition, for service, and for the neighbors who continue to gather beneath it. #SeasideFL

We are honored to share that @usnews has recognize

We are honored to share that @usnews has recognized SEASIDE® as the #1 spot for Best Family Beach Vacations in the nation, a celebration of sun-soaked days, bike rides, and traditions that bring families back generation after generation. #SeasideFL #BestVacations

Today, we remember Elizabeth Campbell, a gracious

Today, we remember Elizabeth Campbell, a gracious presence and an early contributor to the entrepreneurial spirit that helped shape our community.

In 1994, alongside her husband Bill, Elizabeth began McCaskill & Company with a small kiosk in Seaside. What started as a modest storefront grew over time, moving to new locations and becoming our area’s destination for fine jewelry. During their years in Seaside, they were part of a generation of Merchants who believed deeply in the vision of this special place, creating shops that invited gathering, conversation, and connection.

We are grateful for the season she shared with Seaside and for the lasting friendship that followed.

Our thoughts and prayers are with Bill, their family, and all who loved her.

SEASIDE® is designed for families to come togethe

SEASIDE® is designed for families to come together and create lasting memories, and we are committed to preserving that experience. As part of these efforts, SEASIDE® will enforce a 7:00 PM CST curfew for unaccompanied minors (under 18) without parental supervision from March 1 through April 19.

We kindly ask that parents and guardians accompany their children during their visit. While we understand the excitement of independence, Seaside is best experienced as a family. Visit seasidefl.com/curfew to learn more. #SeasideFL

Lunch, but make it poolside. ☀️ The West Side

Lunch, but make it poolside. ☀️ The West Side Grill reopens March 1st and will be serving up seasonal favorites and handcrafted cocktails daily from 11 AM to 4 PM. Settle in, soak up the sun, and enjoy an easy afternoon by the pool in #SeasideFL.

Some gatherings are meant for sunset skies and the

Some gatherings are meant for sunset skies and the sound of the Gulf in the background. A beach bonfire in SEASIDE® turns family reunions, milestone celebrations, and time together into something unforgettable. As the sun goes down and the fire begins to glow, conversations linger a little longer, and memories seem to make themselves. Learn more about gatherings in #SeasideFL through the link in our bio.

A perfect day spent in SEASIDE®. What’s on your

A perfect day spent in SEASIDE®. What’s on your itinerary? #SeasideFL

Sending love from SEASIDE®. Happy Valentine’s D

Sending love from SEASIDE®. Happy Valentine’s Day! ❤️ #SeasideFL

Photos and balloons by @mingle30a. ❤️

17 years of @shrimpshackseasidefl in SEASIDE®. 🦐

Since 2009, The Shrimp Shack has been a go-to for fresh seafood and easy afternoons. From casual lunches to gatherings at the Boardwalk Bar, it’s become part of the familiar rhythm of #SeasideFL. We’re proud to have them as part of our community and grateful for the memories made here year after year. ❤️

Love, SEASIDE® 💌 #SeasideFL is best enjoyed l

Love, SEASIDE® 💌

#SeasideFL is best enjoyed leisurely with time to notice the details, share moments, and let the town unfold around you. Built for connection and designed with intention, every path invites discovery. Find an itinerary that fits your mood and follow it at your own pace. There’s always something familiar to return to and something new waiting to be found. Explore more at the link in our bio!

This is Summer in SEASIDE®. We’re counting down

This is Summer in SEASIDE®. We’re counting down the days to sun-soaked mornings, long afternoons by the water, and evenings that linger just a little longer. ☀️ #SeasideFL

What began as a simple roadside produce stand has

What began as a simple roadside produce stand has grown into a beloved Saturday ritual. The Seaside Farmers Market is now something locals and visitors alike look forward to, an easy gathering place where community, conversations, and fresh finds come together week after week. Join us every Saturday from 9 AM to 1 PM and stroll through a vibrant selection of local vendors offering fresh produce, baked goods, and more.

*Please note there will be no Farmers Market on 2/14 due to the Seaside Neighborhood School Race Weekend.* #SeasideFL #45YearsOfSeaside

As we welcome the Spring Break season in SEASIDE®

As we welcome the Spring Break season in SEASIDE®, we want to take a moment to celebrate what makes our community so special: our commitment to family values and the welcoming atmosphere we extend to all who visit. We are honored that so many families choose Seaside as their Spring Break destination, and we deeply appreciate that tradition.

We want to reiterate our stance on unaccompanied minors to maintain the family-friendly environment that makes Seaside such a cherished place. Seaside is designed for families to come together and create lasting memories, and we are committed to preserving that experience.

In preparation for the upcoming season, SEASIDE® hosted collaborative town hall sessions with neighboring communities, including Rosemary Beach, Alys Beach, WaterColor, and Old Seagrove. These discussions also included the SEASIDE® Town Council, the Walton County Sheriff’s Office, and representatives from short-term rental companies. Together, we established measures to ensure a safe and enjoyable atmosphere for all visitors and locals.

As part of these efforts, SEASIDE® will enforce a 7:00 PM CST curfew for unaccompanied minors (under 18) without parental supervision from March 1 through April 19. We kindly ask that parents and guardians accompany their children during their visit. While we understand the excitement of independence, Seaside is best experienced as a family—exploring our beautiful beaches, enjoying our locally owned shops and restaurants, and making memories that last a lifetime. #SeasideFL

Step inside @headleyhat and discover a space where

Step inside @headleyhat and discover a space where craftsmanship and personal style come together. Browse the selection of hats, then settle in at the custom hat bar to make one entirely your own, from hand-stitching and ribbons to charms and branded details. You’ll also find Tecovas boots, custom trucker hats, and a curated collection of home goods! #SeasideFL

In celebration of the month of love, we’re shari

In celebration of the month of love, we’re sharing the love stories that have shaped the heart of SEASIDE®. ❤️

SEASIDE® Founders, Robert and Daryl Rose Davis, are the love story that started it all. They married at the Tupelo Street Gazebo, with their loyal dachshunds, Bud and Guinness, right by their side. It was simple, personal, and full of meaning.

From the beginning, #SeasideFL has been a place where love shows up in real ways, between people, families, and the community they build together. Have a SEASIDE® love story to share? Send us a message for a chance to be featured. #45YearsOfSeaside

With its striking minimalist design and open-air f

With its striking minimalist design and open-air form, the SEASIDE® Pavilion stands as one of the town’s most architecturally significant and beloved public spaces. It has become a central hub for community life, serving as the starting point for morning yoga classes and a favorite spot to unwind in the evenings. Guests often gather here with al fresco drinks and bites from @pickles_sandbar, settling in for the show that is the sunset over the gulf. Its thoughtful design doesn’t demand attention; it simply enhances everything around it. #SeasideFL #45YearsOfSeaside

Discover an idyllic group getaway where room to ex

Discover an idyllic group getaway where room to explore meets space to connect. In #SeasideFL, gatherings feel effortless, whether for a wellness retreat, a corporate meeting, private celebrations, or life’s meaningful milestones. Gather with intention in a place that encourages connection, collaboration, and lasting memories.

Comment MEMORIES to receive a link to inquire about your next group getaway. #SeasideFL

As one of SEASIDE’S® more decorative beach pavi

As one of SEASIDE’S® more decorative beach pavilions, the Tupelo Street Pavilion is adorned with intricate latticework and pergola-style detailing that casts soft, ever-changing patterns of light throughout the day. Romantic yet refined, its layered design feels both dreamy and intentional, where architecture, sunlight, and the rhythm of the Gulf come together in a quietly beautiful moment. #SeasideFL #45YearsOfSeaside

In #SeasideFL, gatherings unfold in a setting shap

In #SeasideFL, gatherings unfold in a setting shaped by timeless architecture, coastal air, and a deep sense of place. From intimate moments to larger celebrations, each occasion is framed by thoughtful design, open spaces, and the easy rhythm of life by the water.

Across town, a collection of distinct venues offers different ways to mark life’s most meaningful moments. Each venue has its own character and sense of story. Whether it’s a quiet ceremony on the beach or a full weekend of celebration, SEASIDE® provides a backdrop where architecture, nature, and community come together naturally, allowing every gathering to feel personal, intentional, and uniquely you.

Comment VENUE to learn more about our venues and start planning your perfect celebration.

Simple, warm, and quietly integrated into its surr

Simple, warm, and quietly integrated into its surroundings, the Savannah Street Pavilion reflects the understated charm of its street. Designed with natural materials and an unpretentious structure, it serves residents and guests of Savannah Street with a humble but thoughtful beach entry. Its breezy, wood-framed design is as timeless as it is functional. #SeasideFL #45YearsOfSeaside

Long before SEASIDE® became the beloved beach tow

Long before SEASIDE® became the beloved beach town it is today, a small group of creative visionaries gathered after hours, sketching, debating, and dreaming late into the night. Known as the “Night Crew,” they helped imagine and shape a town built on ideas, thoughtful architecture, intentional planning, and the belief that community matters.

Today, we welcome hundreds of thousands of visitors each year, but at our core, we remain rooted in those early evenings of collaboration, where design, culture, and shared experiences were woven together to create something lasting. #SeasideFL #45YearsOfSeaside

The East Ruskin Beach Pavilion feels like a piece

The East Ruskin Beach Pavilion feels like a piece of art set against the shore. Light and shadow move across its geometric form throughout the day, creating moments that feel different each time you pass through. It’s a favorite stop for those who love thoughtful design, lingering sunsets, and seeing the beach from a fresh perspective. #SeasideFL #45YearsOfSeaside

Join us in wishing a Happy Birthday to SEASIDE® c

Join us in wishing a Happy Birthday to SEASIDE® co-founder and @theseasidestyle founder, Daryl Rose Davis! Her creativity, leadership, and dedication have helped shape #SeasideFL for decades, and we are endlessly grateful for the impact she continues to make. ✨

Each door in #SeasideFL has its own story to tell.

Each door in #SeasideFL has its own story to tell. ✨

A stroll through SEASIDE®. #SeasideFL Photos by

A stroll through SEASIDE®. #SeasideFL

Photos by @whit.jpg_.

Rising from the dunes with its unmistakable obelis

Rising from the dunes with its unmistakable obelisk form, the Coleman Pavilion stands as SEASIDE®’s most iconic gateway to the Gulf. As the town’s central beach access, it sets the scene for sun-filled beach days, beach bonfires, quiet moments, photographs, celebrations, and golden-hour sunsets. #SeasideFL #45YearsOfSeaside

Meet Desiree and Whitley, the faces and heart behi

Meet Desiree and Whitley, the faces and heart behind @drome_seasidefl.

Their story began in China, where they met, and eventually led them back to the U.S., settling together in Whitley’s hometown of Auburn, Alabama. From there, they launched a food truck serving the flavors of Desiree’s Northeast China roots, while experimenting with creative twists that blended Chinese street food with American favorites. The response was immediate and overwhelming. That creative spark grew into a beloved Auburn restaurant, and in 2025, their journey brought them to SEASIDE®.

Today, Drome is a reflection of their story: bold, thoughtful, and rooted in connection. We’re grateful their path led them to SEASIDE® and proud to have Desiree and Whitley as part of our community. 🤍 #SeasideFL

The West Ruskin Street Pavilion offers a more inti

The West Ruskin Street Pavilion offers a more intimate approach to the Gulf, one rich with meaning and craftsmanship. Designed by New York–based architect Michael McDonough, its layered wooden details draw from Southern traditions like quilting, lumber yards, and even the American flag. The structural elements and subtle architectural illusions invite residents and guests alike to pause, look closer, and consider the story unfolding around them, reminding us that in SEASIDE®, the journey to the beach is as intentional as the destination itself. #45YearsOfSeaside #SeasideFL

For two unforgettable days the @30afest brought to

For two unforgettable days the @30afest brought to SEASIDE® world-class artists and storytellers. Our community became a place where songs found their way into the evening air, carried across the Lyceum Lawn, @budandalleys, @centralsquarerecords , @pickles_seasidefl, and echoing through the Amphitheater.

From Margo Price’s powerful presence on Friday afternoon in the Amphitheater to intimate, story-driven sets by Darrell Scott, Josh Rouse, and Chris Stills, each performance felt personal. On Saturday night we gathered once more for incredible moments from Lera Lynn, Rhett Miller, David Ryan Harris, and a breathtaking close with I’m With Her, reminding us why songwriting is best experienced up close. Thank you to every musician, storyteller, and guest who turned our community and stages into something unforgettable.

Until next year, @30afest. 🎶

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