What The Leading Ladies Of Who's The Boss? Look Like Now
Whether you were drawn to corporate ad exec Angela (Judith Light), trendy teen Samantha (Alyssa Milano) or flirty age-knows-no-bounds grandmother Mona (Katherine Helmond), there was plenty to attract folks to the leading ladies of the '80s TV hit "Who's the Boss?" Helmond, who earned two Emmy nominations and a Golden Globe for her role as the free-spirited grandmother, passed away in 2019, at age 89. Looking back at pics from the show's heyday in the '80s and '90s, Helmond's aesthetic has arguably aged the best with her sexy-meets-sophisticate vibe. Her on-screen daughter Angela, played by Light, has had more of an extreme transformation through the years, however.
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Judith Light has left Angela Bower's voluminous '80s feathered hairstyle behind. Pictured in May 2026 at age 77, Light now wears her blond hair in straight layers, which is one of the long hairstyles that are so flattering on older women. "The Terror" actor is also still playing with makeup, including an edgy take on an amplified lower lash line, heavily lined and fringed with mascara.
Despite still looking fabulous in her 70s, Light says she has embraced aging. "If I'm the same as I was yesterday, then I'm not really learning anything," she told Salon in 2022. "These are the wise years."
Like Judith Light, Alyssa Milano's hair has also taken a chill pill since the '80s
From her time on "Who's the Boss?" to her years on "Charmed" through to now, Alyssa Milano has had a stunning style transformation. She's gone from America's favorite '80s sitcom daughter-of-a-single-dad to an elegant 50-something (she hit the half-century mark in 2022) who is still acting. Thanks to that transformation, Milano is one of the '80s child stars that are practically unrecognizable now.
Back when she was playing leading young lady Samantha, despite having naturally straight hair, Milano sported many era-defining hairstyles, including bouncy ponytails, full curls, and "mall bangs," all courtesy of copious doses of hair spray, undoubtedly. Fast-forward to the 2020s when Milano makes elegant beauty statements appropriate for the times. For example, at a movie screening in June 2026, she had a strong makeup look with defined eyes, brows, and lips, which she balanced with a deep side-part and low ponytail. In May of the same year, she wore a halo braid and raspberry lips. In the fall of 2023, she sampled bangs and a fuchsia lip, showing that this Brooklynite has versatility in spades.