The resurgence of overalls—both long and short (shortalls)—is a cornerstone of the "New Vintage" movement, driven by a global desire for durable, gender-neutral, and comfort-first apparel. During the 1990s and early 2000s, overalls transitioned from functional blue-collar workwear to a high-fashion and pop-culture phenomenon, famously styled by icons like TLC, Will Smith, and Jennifer Aniston. The 90s aesthetic was defined by an oversized, "anti-fit" silhouette often worn with one shoulder strap unbuckled to signal a rebellious, laid-back attitude, while the Y2K era introduced more adventurous iterations including color-blocked fabrics, corduroy, and even cargo-pocket styles.
The popularity of overalls in these decades was anchored by a specific group of heritage and streetwear brands that remain highly collectible today. Carhartt stood as the gold standard for rugged authenticity, becoming a staple in the NYC hip-hop scene and skateboarding subcultures due to its heavy-duty duck canvas and triple-stitched seams. For those seeking a more fashion-forward or preppy look, Tommy Hilfiger and Polo Ralph Lauren dominated with designs featuring large, embroidered logos and vibrant primary colours. Levi's and Lee remained essential for classic denim enthusiasts, while OshKosh B'gosh (especially their "big kid" and adult lines) and Dickies offered a practical, utilitarian edge. In the mass market, Old Navy and Gap produced millions of light-wash shortalls that defined the quintessential suburban summer look of the late 90s.
