From high school sweethearts to a decade-long love story, influencer Mason Oglesby and Zachary Annis have truly grown up side by side. On April 18, 2026—a date chosen with intention and meaning—they officially began their next chapter. “We started dating when we were 17,” Mason shares. “After ten years together, you don’t always expect moments to feel entirely new—but our wedding day did.”
California has always held a quiet significance in Mason’s life. After briefly living in Orange County post-grad, she and Zack created a ritual of driving along the Pacific Coast Highway, something that made the West Coast feel like home. Even after moving to Chicago, they returned often. In 2024, what Mason thought was a work trip turned into something much more. Zack orchestrated a surprise proposal disguised as an influencer event in Malibu, enlisting her closest friends and even flying in her best friend from home. “When I walked inside, the first thing I saw was a dress I had mentioned months earlier,” she recalls. “That’s when I realized what was happening.” As the sun set over the Malibu hills, Zack proposed. The celebration that followed—In-N-Out, Champagne, and a weekend overlooking the coast—set the tone for everything to come.
When it came to the wedding, Mason always knew she wanted to be married along 30A, a place that had long felt like a second home. Finding the right venue, however, required patience. That patience paid off when her family discovered Kaiya Beach Resort, a property still in development at the time. “We were one of the first couples involved in conversations about how the space could host weddings,” she explains. “Watching it come to life while planning our wedding there felt like a dream.” With Carolyn Touchette Events leading design and planning, the vision came together seamlessly with an aesthetic that felt like a European garden layered with coastal ease.
Fashion became one of the most meaningful parts of the entire experience. Mason documented her year-long dress search online, trying on nearly 100 dresses before finding the one with Netta BenShabu during New York Bridal Fashion Week—exactly one year after her engagement. “When I put it on, there was a sense of clarity I hadn’t felt before,” she says.
Her dress featured a basque waist with lace and pearl detailing, finished with a soft tulle overskirt that allowed for multiple looks throughout the night. The pearl elements carried into her custom jewelry by Gage Diamonds, the same team Zack worked with on her engagement ring, adding a layer of continuity to each look. Hair by Reese Bond Hair and makeup by Kiss and Makeup by Steph completed Mason’s look with a timeless feel, including a soft side part that nodded to how she wore her hair when they first met.
Mason's fashion story extended throughout the weekend. For the rehearsal dinner, she worked with Mira Couture to create a custom Old Hollywood–inspired dress with silky textures and feather detailing. Later in the night, she changed into the “Mason Mini,” a pearl dress named after her, which set the tone for a more relaxed, after-hours feel. Zack’s wardrobe, curated with Suitsupply, reflected the same balance of timeless and personal, from his custom tuxedo on the wedding day to lighter, patterned looks for the weekend’s earlier events.
The wedding weekend began with a rehearsal dinner at Raw & Juicy Alys Beach, where décor and catering by CC Boone created a setting that felt both elevated and welcoming. Custom stationery by Artfully Overjoyed and music by Blaine Holcomb added thoughtful, personal touches that carried into the wedding day.
Captured by Masters & Masters Weddings, the celebration at Kaiya Beach Resort unfolded in a setting that was both intimate and expansive. Officiated by their close friend Luke Corbett, the moment was deeply personal from the start. “The second I saw Zack, everything else faded,” Mason shares. “It truly felt like it was just the two of us.”
After the couple was announced as officially wed, guests were welcomed into cocktail hour with elevated comfort food by Townsend Catering Company: truffle fries, mac and cheese bites, and salmon. One of Mason’s favorite details was the tray service, where waiters passed Champagne and Coca-Cola on vintage silver trays sourced by friends and family.
Flowers from Florals by the Sea and rentals from HM Event Rentals and Longleaf Events brought the bride's vision to life with tables that felt simple, timeless, and ethereal. The cake by Sweetly Sisters 30A added a final, delicate touch to the design.
As the night unfolded, heartfelt toasts from family and close friends set the emotional tone before the dance floor opened with music by Mr. Evan Howard. Their first dance to "Coastline" by Hollow Coves reflected their journey—one built on change, movement, and choosing each other through every phase. “My favorite part was watching Zack completely let loose,” Mason says. “It changed the energy in the room—everyone fed off of it.”
The night transitioned naturally into a more intimate after-party, with guests gathering at nearby villas on the property. Mason changed into her Mason Mini, and the celebration continued with pizza, cake, Pop-Tarts, and wine by the pool. “It felt less like a formal event and more like a late-night hang with all of our favorite people,” she says. “Exactly how we wanted to end it.”
While the couple is saving their full honeymoon for next year—planning a return to Europe with stops in France and Rome—they began married life with a mini-moon in the Cayman Islands, already looking ahead to their next chapter together.
