Leopard Pillbox Hat Worn by Pamela Anderson Emerges as Unexpected Fashion Trend of Autumn
In a surprising turn of events, the pillbox hat - once a staple of mid-century fashion - is making a notable resurgence in popularity in 2025. This revival can be seen prominently on runways and streets alike, aligning with a broader nostalgic turn in fashion.
The small, flat-topped, and brimless pillbox hat, while an unlikely choice for some, has found favour with PR professional Pirrie Wright, who notes that about 1 in 100 people she encounters wear pillbox hats on the street, signaling a marked surge in everyday wear.
This comeback is not a solo attempt by any fashion icon. Fashion consultant and content creator Leila Kashanipour has been championing vintage headwear, showcasing a variety of turbans and pillbox hats to her 140k+ following. Kashanipour's advocacy includes the revival of pillbox hats, which are often paired with romantic, pastel, and sporty fall collections.
The trend appeared strongly at Copenhagen Fashion Week and is linked to the revival of retro beauty and fashion elements such as head scarves and oversized scrunchies. For fall 2025, pillbox hats are integrated into ensembles including knit twinsets and skirt suits reimagined with modern fabrics and sporty touches, aimed at practical yet stylish "on-the-move" women.
While specific brand names were not detailed in the search results, the context implies that both luxury designers and vintage/vintage-inspired labels are likely part of this trend. The emphasis on vintage shops and reworked classic pieces suggests that capsule collections or retro-inspired lines from both high-end fashion houses and contemporary boutiques contribute to the pillbox hat's comeback.
One notable example of this revival can be seen in Pamela Anderson's recent styling. Anderson, known for her unique hats, has been spotted wearing a leopard-print pillbox hat, reminiscent of Jackie Kennedy's style. The leopard-print pillbox hat was styled with a black wool faille cape dress, a leather 'Hug' belt, matte black leather 'F-buckle' pumps, and face-framing curls.
This places the pillbox hat as a key accessory that blends heritage with contemporary styling in the current fashion landscape. Fashion, as mentioned by Leila Kashanipour, is cyclical in nature, suggesting that trends may repeat themselves. This places the pillbox hat as a key accessory that blends heritage with contemporary styling in the current fashion landscape.
It is worth noting that this resurgence in the pillbox hat's popularity is not limited to Pamela Anderson. Other vintage-inspired pieces Anderson has worn include cat-eye sunglasses, a pussy-bow blouse, and a flowing lemon maxi skirt with a matching Ralph Lauren cable-knit sweater. Pillbox hats have made a notable appearance on the Spring/Summer 2025 runways of Chloé, Loro Piana, and Valentino.
The pillbox hat historically gained fame in the 1960s, particularly through iconic figures like Jackie Kennedy, symbolizing sophisticated and polished femininity. Its small, flat-topped, and brimless design makes it a distinctive, structured accessory.
In conclusion, the pillbox hat is making a comeback in the fashion world, with a notable resurgence in popularity in 2025. This revival aligns with a broader nostalgic turn in fashion, drawing on timeless, elegant styles reminiscent of mid-20th century glamour. The pillbox hat is often paired with styles that evoke romanticism and femininity, featuring sheer fabrics, ruffles, pastel hues, and soft textures which reflect current fashion movements toward softer, nostalgic aesthetics.
- Leila Kashanipour, a fashion consultant and content creator, has been promoting vintage headwear, such as turbans and pillbox hats, to her 140k+ following, contributing to their resurgence in daily wear.
- The current reemergence of the pillbox hat in the fashion world can also be attributed to celebrities like Pamela Anderson, who has been spotted wearing this nostalgic accessory, such as a leopard-print pillbox hat, echoing Jackie Kennedy's style.
- These retro-inspired pieces, found on the Spring/Summer 2025 runways of numerous high-end brands such as Chloé, Loro Piana, and Valentino, demonstrate the growing interest in the blend of heritage and contemporary styling that the pillbox hat represents.
- This revival of the pillbox hat signifies more than just a standalone trend, but a broader shift in fashion towards romantic, nostalgic aesthetics that sit well with today's lifestyle and entertainment influences.
