Jessica Ashley: A Visionary Wedding Planner Who Blends Design and Emotion

AUTHOR: Natali Grace Levine

READING TIME: 4 min 52 sec

PUBLICATION DATE: 02/25/2025

UPDATED: 02/25/2025

Content

“My soul ignited when I planned my own wedding, sparking a lifelong passion that turns work into pure joy.” This is how Jessica Ashley, the visionary behind Jessica Ashley Events, describes the moment that changed everything for her. Unlike many traditional planners, Jessica is entirely self-taught, embracing a fresh perspective that merges wedding planning with interior design.

“I sidestep the outdated methods often seen in hospitality-trained planners. Instead, as both a planner and interior designer, I bring a fresh perspective and a vibrant eye to every detail.”

Since 2017, Jessica has been curating stunning weddings in Washington DC, Florida, and destination locations, crafting experiences that leave guests in awe. “My goal? To deliver a 5-star luxury experience that leaves you and your guests in awe, with jaws still dropping weeks later.”

The First Wedding: A Lesson in Intimacy and Detail


Jessica’s journey into wedding planning began with a heartfelt backyard tented wedding in Maryland. Though small in scale, it was an experience that shaped her approach to planning. It wasn’t a grand ballroom affair, but it taught her early on that the best weddings are not about the venue, but about the emotions and experiences created within it.

Crafting Experiences That Tell a Story

“What I love most about wedding planning is the opportunity to tell each couple’s unique story through design and experience,” Jessica explains. “Every wedding is a reflection of who they are.” Her approach is deeply personal, ensuring that no two events ever feel the same. “Most of all, I love the joy of seeing my clients and their guests completely immersed in the magic of the moment, knowing they feel celebrated and cared for at every turn.”

A Philosophy Rooted in Artistry and Excellence

Jessica Ashley Events thrives on curating weddings that defy convention while embracing individuality. “We love planning weddings that challenge convention and embrace individuality,” she shares. “Whether it’s a bold and fashion-forward celebration, a destination wedding infused with cultural significance, or an intimate affair with layered details, we thrive on creating events that are as unique as our clients.”

One of her greatest passions is crafting immersive guest experiences. “We particularly enjoy designing weddings where we can elevate the guest experience—ensuring every detail, from the decor to the entertainment, creates a five-star atmosphere.”

Tailored Services for Every Couple

Jessica Ashley Events offers a full-service approach to wedding planning, ensuring that every element of the event is handled with precision. “Our services include full-service planning, event design, and comprehensive coordination, ensuring every aspect of your wedding is meticulously managed from start to finish.”

In addition to traditional planning, Jessica offers interior design services, virtual wedding design for couples planning remotely, and mentorship for aspiring planners and designers. “While full-service planning is our specialty, we understand that every couple’s needs are unique. We’re happy to work closely with you to tailor a package that aligns with your vision, priorities, and wedding day goals.”

A Wedding That Stood Out: A Bold and Artistic Affair

“One of the most memorable weddings I’ve ever planned was an eclectic celebration inspired by the bold, vibrant aesthetic of Farm Rio at Glenstone Gardens,” Jessica recalls. “The bride, also an interior designer, brought a shared passion for layered details and thoughtful design, making this collaboration incredibly meaningful.”

The wedding was a masterclass in design storytelling. “We began with a serene neutral palette for the ceremony, creating a calm and timeless foundation. As guests moved into the cocktail hour, pops of vibrant color and fresh citrus were introduced, signaling the start of the celebration. Finally, the reception tent burst into an explosion of bold, vibrant hues, reflecting the couple’s joyful spirit.”

A Thoughtful and Strategic Approach to Planning

Jessica emphasizes the importance of collaboration and communication. “I start by getting to know them on a personal level—learning about their style, what inspires them, and the experiences they want to create for themselves and their guests.” She works closely with her clients to ensure that their vision is fully realized. “From there, I guide them through a tailored planning and design process, ensuring every detail aligns with their desired outcome.”

Expertise in Estate and Destination Weddings


Jessica specializes in private estate tented weddings, which allow for complete customization and flexibility. “These events allow us to create truly one-of-a-kind celebrations, blending natural beauty with bespoke design.” One of her favorite venues is Glenstone Gardens. “Whether it’s a private estate, a luxury garden venue, or a unique destination, we love working in spaces that offer the flexibility to craft an unforgettable experience tailored to our clients.”

Facing Challenges with Creativity and Grace

Every wedding planner encounters unexpected challenges, and Jessica is no exception. “One of the biggest challenges I’ve faced is navigating unexpected changes or limitations while ensuring the wedding still feels flawless and intentional.”

Weather unpredictability is one of the biggest hurdles. “Outdoor weddings often come with weather unpredictability, and I’ve had to pivot quickly—rearranging layouts, adjusting timelines, or enhancing decor elements to accommodate last-minute shifts.” The key, she says, is adaptability. “The key in those moments is staying calm, thinking creatively, and leaning on my trusted vendor team (including a personal meteorologist) to execute a seamless solution.”

Budgeting with Transparency and Strategy

Jessica believes in educating couples about the budgeting process. “We approach budgeting as a collaborative and educational process, ensuring our couples feel confident and informed every step of the way.” She emphasizes the importance of prioritization. “Having this clear from the start allows you to allocate your budget accordingly and ensures your planning is guided by what truly matters to you as a couple.”

Words of Wisdom for Couples Planning Their Big Day

Jessica encourages couples to focus on what truly matters. “My biggest advice for couples planning their wedding is to start by creating a list of priorities or non-negotiables. These are the elements that matter most to you—whether it’s the venue, food, entertainment, or design details.”

She also stresses the importance of perspective. “Planning a wedding is about balance, and prioritizing what’s meaningful will help you feel confident in your decisions while still creating a celebration that feels uniquely yours.”

Advice for Aspiring Wedding Planners

Reflecting on her own journey, Jessica offers advice for those entering the industry. “If I could give advice to my younger self, I’d say to embrace every opportunity and use it as a stepping stone to refine your craft.”

She also highlights the value of self-discovery. “Each experience, no matter how small, was a chance to learn, grow, and build confidence in my abilities.” Jessica urges new planners to lean into their strengths. “Once I identified my passion for luxury, design-driven events, I leaned into those strengths and worked to elevate myself within the wedding world.”

A Dream Wedding Destination

Jessica dreams of planning weddings at some of the most luxurious locations in the world. “My dream wedding venue would be The One&Only Palmilla in Cabo—it’s such an extraordinary location, blending stunning coastal views with an unparalleled sense of luxury.”

Another dream destination? Lake Como. “The breathtaking scenery, timeless architecture, and romantic atmosphere make it the perfect backdrop for creating a truly unforgettable wedding.”

With a passion for storytelling, design, and unforgettable experiences, Jessica Ashley Events continues to redefine luxury wedding planning, creating celebrations that leave lasting impressions on couples and their guests alike.

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