In our continuing series spotlighting women entrepreneurs who are redefining their industries, we sit down with Annabelle Holmes, the visionary wedding planner behind some of New York City’s most distinctive celebrations. Holmes has carved out a unique niche in the saturated wedding market by specializing in gothic and dark romance aesthetics that maintain sophistication and emotional resonance.
Females Who Lead: Annabelle, your work in the wedding planning space has garnered attention for its distinctive aesthetic. How did you first identify this underserved niche in the market?
Annabelle Holmes: I noticed a consistent pattern while working in traditional wedding planning. Certain couples would always push for something darker, more dramatic—but they weren’t finding planners who understood their vision without turning it into something costume-like. There was this significant group of clients who wanted elegance and sophistication but through a darker lens. They didn’t want their wedding to feel like a Halloween party; they wanted it to feel like them. That gap between what these couples envisioned and what the industry was providing became my opportunity.
Females Who Lead: The wedding industry in New York City is notoriously competitive. What strategies did you employ when launching your business to differentiate yourself?
Annabelle Holmes: When I first started, I focused intensely on building a portfolio that showcased exactly the kind of work I wanted to attract. Rather than trying to be everything to everyone, I invested in styled shoots that highlighted my aesthetic—dark dahlias, black calla lilies, vintage brass candlesticks, and dramatic lighting schemes. This meant turning down work that didn’t align with my vision initially, which was financially challenging but strategically essential. I also built relationships with vendors who could execute these unconventional elements beautifully—florists comfortable working with darker palettes, photographers who understand how to capture dramatic lighting, and venues with architecture that complemented the gothic aesthetic.
Females Who Lead: Your business model seems to involve a higher-touch, more personalized approach than mass-market wedding planning. How have you structured your operations to maintain profitability while providing this level of service?
Annabelle Holmes: I deliberately keep my client roster small—I take on no more than fifteen full-service weddings annually. This allows me to provide the attention to detail these complex designs require. To maintain profitability with fewer clients, I’ve created multiple service tiers. While full-service planning is our flagship offering, we also provide design consultations and à la carte services for couples who might handle the logistics themselves but need guidance on aesthetic execution. Additionally, I’ve developed workshops for other wedding professionals looking to expand their design repertoire, which creates an additional revenue stream that doesn’t require the same time investment as full-service planning.
Females Who Lead: You’ve mentioned the importance of building the right team. What qualities do you look for in collaborators, and how have you approached growing your business beyond yourself?
Annabelle Holmes: When building my team, technical skill is obviously important, but I primarily look for individuals who have an inherent understanding of balance—knowing how to push boundaries while maintaining sophistication. My first hire was actually a former art history major who had worked in gallery curation. She inherently understood how to create atmospheric experiences and could translate clients’ sometimes abstract desires into concrete design elements.
I’ve grown intentionally slowly, bringing on specialists rather than generalists. For instance, I have a calligrapher who specializes in Victorian-inspired lettering for our hand-calligraphed love letters and place cards, and a lighting designer who previously worked in theater. This specialized approach means each team member brings depth in their particular area rather than breadth across many areas.
Females Who Lead: The pandemic forced many wedding entrepreneurs to pivot dramatically. How did you navigate those challenges?
Annabelle Holmes: The pandemic was actually a fascinating inflection point for us. While it initially brought postponements and cancellations, it ultimately accelerated certain aspects of our business. As restrictions eased, many couples were drawn to smaller, more intimate celebrations—which aligns perfectly with the atmospheric, detail-rich experiences we create. The desire for meaningful, personalized experiences intensified after people spent so much time apart.
We also used the downtime to refine our digital presence and systems. We created detailed digital showcases of our previous work and developed a more robust consultation process that could function virtually. These adaptations have remained valuable even as in-person events have returned, allowing us to serve clients who might not be local to New York during the planning phase.
Females Who Lead: You’ve become known for integrating Victorian-inspired elements with modern touches. How do you stay innovative while honoring these classical influences?
Annabelle Holmes: I’m constantly studying both historical design and contemporary art movements. I might spend a weekend visiting the Victorian wing at the Metropolitan Museum of Art, then attend a modern installation at a Chelsea gallery. Innovation often happens at the intersection of these seemingly disparate influences.
I also make it a point to explore adjacent creative fields—fashion, interior design, even film production design. Some of our most successful tablescape concepts have been inspired by costume design from period dramas, reimagined through a contemporary lens. This cross-disciplinary approach keeps our work from becoming formulaic.
Females Who Lead: What have been some of the most significant challenges you’ve faced as a woman entrepreneur in this space?
Annabelle Holmes: The wedding industry is female-dominated in many ways, but there are still challenges. One of the most persistent has been being taken seriously when pushing for unconventional approaches. There’s sometimes an assumption that feminine aesthetics must be lighthearted and pretty in a traditional sense. Creating spaces that are feminine but also dramatic and sometimes even slightly macabre challenges certain preconceptions.
From a business perspective, securing financing for growth was challenging. Despite having a proven track record and reliable profit margins, traditional lenders often seemed uncomfortable with a business model focused on “dark” weddings. I eventually found success with women-led investment groups who understood the vision more intuitively.
Females Who Lead: How do you handle the emotional aspects of wedding planning while running a business? These are high-stakes events for your clients.
Annabelle Holmes: This is where keeping our client list small becomes crucial. Each wedding receives my full attention, and I build genuine relationships with my couples. I’ve structured our planning process to include regular check-ins that go beyond logistics to address how clients are feeling about the process. Before making any major design decisions, we discuss not just how something will look, but how it will feel emotionally when experienced.
The business side requires a different mindset, so I’ve established clear boundaries around when I’m working on creative aspects versus operational tasks. Monday mornings, for instance, are dedicated exclusively to business operations—reviewing finances, addressing team needs, and strategic planning. This compartmentalization helps prevent burnout and ensures neither aspect suffers.
Females Who Lead: Your work emphasizes sophisticated gothic aesthetics. How do you help clients navigate family expectations when they’re choosing a non-traditional approach?
Annabelle Holmes: This is such an important aspect of our work. We actually build family communication strategies into our planning process. First, we help couples identify which traditional elements hold personal meaning for them versus which ones they’re considering solely for others’ expectations. Then we explore ways to honor meaningful traditions through our aesthetic lens.
I remember working with a bride whose grandmother was concerned about the black wedding dress she wanted to wear. We invited the grandmother to a private design session where we showed her the exquisite craftsmanship and incorporated family lace into the veil. Seeing the thoughtfulness behind the choice completely changed her perspective.
We also create visual presentations for families that help them envision the final result. Often, their hesitation comes from simply not being able to picture how elements will come together with sophistication rather than looking theatrical.
Females Who Lead: What advice would you give to women entrepreneurs looking to establish themselves in saturated markets?
Annabelle Holmes: First, specificity is your friend. Don’t try to appeal to everyone—identify the clients who aren’t being served well and focus intensely on meeting their needs. Second, document everything beautifully. In visual fields especially, the quality of your portfolio will speak volumes about your capabilities.
Third, build a network of peer entrepreneurs rather than viewing everyone as competition. Some of my most valuable business insights have come from relationships with planners who serve completely different markets. We can share operational challenges and solutions without competing for the same clients.
Finally, know your numbers intimately. Creative entrepreneurs sometimes shy away from the financial aspects of business, but understanding your profitability at a granular level empowers better decision-making. I review my business metrics weekly and make adjustments accordingly, which has allowed me to grow sustainably rather than in unsustainable bursts.
Females Who Lead: Looking toward the future, how do you see your business evolving?
Annabelle Holmes: I’m currently developing a limited collection of physical products that embody our aesthetic—custom candle vessels, textile pieces, and paper goods. These allow clients to bring elements of their wedding into their homes, extending the emotional connection to the day.
I’m also exploring opportunities to share our approach through educational content for other wedding professionals. There’s significant interest in understanding how to create these atmospheric experiences, and developing this knowledge-sharing aspect of the business allows our influence to extend beyond the number of weddings we can physically produce.
Ultimately, I see us continuing to refine rather than expand. I’m interested in creating increasingly distinctive experiences for our select clientele rather than scaling to serve more couples. This commitment to depth over breadth has guided our growth so far and will continue to shape our future.
Females Who Lead: Thank you for sharing your entrepreneurial journey with us, Annabelle.
Annabelle Holmes: Thank you for the opportunity to discuss the business aspects behind our creative work. Building something that honors both artistic vision and sound business principles has been the most rewarding challenge of my career.
This interview is part of our ongoing Females Who Lead series, profiling entrepreneurs who are bringing innovation to established industries through distinctive vision and strategic execution.