Madonna's Best-Dressed Moments In Her Most Iconic Style Decade: The '80s

Madonna is one of the few pop superstars who has managed to stay in the spotlight for over 40 years — not an easy feat! The musical icon truly has something special — she's constantly reinventing herself. While our plastic surgeon has confirmed that Madonna's face has transformed over the years, it's her epic style moments that we seem to remember time and time again. She's had many incredible decades filled with out-of-this-world fashion choices, but nothing brings us back like revisiting her roots. The 1980s were when things really took off for Madonna, thanks to the release of her iconic album "Like a Virgin." The release cemented that time as a pivotal moment in her career.

This was when Madonna proved that she wasn't interested in being like everybody else — especially when it came to her fashion choices. She even paved the way for future generations. Many craze we see in the current decade (like the 2023 lingerie trend making underwear undeniably chic) stemmed from a time when Madonna wore things like boudoir-inspired tops, vintage DIY fashion, and boundary-breaking award show ensembles. Many of these outfits continue to live rent-free in our brains.

While posing for a portrait in Los Angeles, California, in 1989, Madonna was seen wearing this to-die-for cropped white blazer and pants set. This look is so fashion-forward yet quintessentially '80s. Boxy blazers with shoulder pads were en vogue back then, and we imagine Madonna took notes from other pop superstars like Prince while keeping her finger on the pulse. She's always been known for keeping ahead of the curve with her music — it's nice to see that attitude also extended to her fashion choices.

While many singers transition into acting work later in their career, Madonna made her acting debut right alongside the start of her music career. The above photo was taken of Madonna on set of her movie "Who's That Girl?" in 1987 where she played ex-convict Nikki Finn. "I liked her dual personality — her tough side and her sweet side," Madonna said of her character in a 1987 interview. This outfit definitely mirrors that energy. The look featured a grungy, vintage-looking oversized coat and newsboy cap, and Madonna finished it off with a bold, feminine red lip.

In August 1986, Madonna and her ex Sean Penn were seen in New York leaving a rehearsal of a play they starred in together called "Goose and Tomtom." Madonna was all smiles in another quintessentially '80s 'fit. The belted dress and leggings combo was such a classic sign of the times. She looked so effortless yet incredibly fashion-forward at the same time. Madonna also told Refinery 29 in a 2018 interview that she was broke early in her career, so we imagine she was a serious thrift store queen, and called upon that influence when styling outfits like this.

In 1987, Madonna was seen rocking this sleek monochrome 'fit while out prowling the streets of Los Angeles, California. The superstar was seen often wearing all-black ensembles at various airports during her 1985 "Virgin" tour, so this wasn't a one-off. She always managed to look effortlessly cool and this black leather jacket and pants gave Marilyn Monroe energy. Both women were (and still are) icons and had a knack for dressing smart and sharp while ultimately breaking boundaries (see the Marilyn Monroe outfits that meant more than you knew).

Long before lingerie bodysuits and tops were trending in the 2020s, Madonna wore this style while performing in Los Angeles, California, in 1989. According to Vogue Mexico, Madonna frequented the New York club Fun House early on in her career and she built many of her iconic looks in the '80s around New York club culture. This meant many a lingerie-inspired outfit which she would often pair with other streetwear items, like Nike biker shorts, for an added edge. 

In addition to her love of a good lingerie bodysuit or top, Madonna also loved adding tons of accessories like chunky jewelry, belts, and lace gloves. One of her most memorable looks was this white outfit she wore to the 1984 MTV Video Music Awards. The standout accessory here was her cheeky belt that said "boy toy." It really goes to show the pop musician wasn't ever interested in blending in — she wanted to disrupt the industry with her heavily New York-influenced, street-style outfits.