The ‘Shady Lady’ of hats turns from TV producing to fashion

Based in Fairfield, Allyson Mandelbaum transitioned from a reality TV producer to a milliner with a distinct vision. After 20 years in the television industry, working on series like “My Super Sweet 16” and “90 Day Fiancé,” she has redirected her focus toward a long-standing passion – fashion.

The concept of Shady Lady Hats, she told the Westfair Business Journal, was anchored in innovation and practicality. As a busy mother of two, Mandelbaum had noticed a gap in the market for well-fitting, stylish baseball caps, having observed that caps were generally designed for men but knowing that men’s and women’s skulls were differently shaped.

This unmet need drove her to establish a business that would combine fashion with functionality.

If “shady” as a description can be ambiguous, Mandelbaum was resolute that “Shady Lady” carried no negative connotations. The word, she said, was “strategic” – capturing the essence of style and intrigue as she saw it. This branding decision was informed by feedback from trusted colleagues, aligning with Mandelbaum’s own vision for the product line.

Building a foothold in the competitive fashion industry demanded careful financial planning. Mandelbaum started the business using her own capital, developing an initial inventory of 2,000 hats in 2020. Lean operations, complemented by advice from local mentors and resources such as the Women’s Business Development Council in Stamford, fostered a sustainable growth trajectory.

Still, the business faced several operational challenges, including high shipping costs, which led to early policy adjustments, such as requiring a minimum purchase for free shipping. The entrepreneurial journey, she said, had been unpredictable, demanding resilience and a supportive network to navigate the fluctuations typical of solo-led businesses.

Mandelbaum’s creative process involves converting spontaneous ideas into vivid sketches, reflecting influences from 1960s symbols like the peace sign (actually Gerald Holtom’s iconic sign for the British Campaign for Nuclear Disarmament) and versatile patterns like camouflage and leopard print. The black-and-white yin and yang symbol is another easily recognized motif she unashamedly incorporates into her designs – which offer an alternative to standard choices and, most important, appeal to customers, she said.

She added that Shady Lady Hats aims to be recognized not only for its creativity but also for its focus on community engagement and sustainability. The company, having achieved a consistent annual sales growth of 50%, was already commited to donating a portion of profits to initiatives for environmental restoration, particularly in marine areas.

Looking forward, Mandelbaum’s strategy involves expanding Shady Lady, which is limited at present to baseball and trucker hats; “statement” beanies in bold colors (the pink, navy and neon green winter beanie stating “It’s cold” has already sold out); kids beanies and a selection of totes. She said she wants Shady Lady to become a preferred brand for women’s hats, distinguishing products by their specificity to women’s sizing. Collaborations with women-centric organizations, she hopes, will further bolster this vision and set some new industry standards along the way.

The takeaway? In an industry driven by transient trends, Shady Lady Hats exemplifies the potential for small businesses to blend a gap in the market with strategic innovation, offering products that serve practical needs while yielding sufficient profits to give something back to the community.

Hats off – or rather on, we say – to that.