The 25 Best Prince Fashion Moments, and The Eras That Went With Them

We first met Prince in 1978 as a 20-year-old with his debut studio album Soft and Wet. With that debut also came luxurious silky afro that was poofed to perfection. Even back then Prince never had a hair out of place, giving us one of the most symmetrically perfect afros we've ever seen. Shoutout to that leather jacket too—it was smooth.

Enter the jerry curl. Everybody who was somebody had a jerry curl at some point in the 1980s, and Prince hopped on the trend relatively early. While Controversy wasn’t his breakout album (that would come the following year with 1999), the cover captured attention with Prince wearing a taupe sequin jacket over top of a tuxedo vest and tie. 1981 was also the first year (at least from a national standpoint) where we saw Prince rocking his signature heavy eyeliner.

Only Prince could have gotten away with an outfit like this and only he could have made it iconic. Look at it—the man is wearing a bandana in place of a shirt, thong underwear, and thigh high boots. We do have to add that Prince originally started the performance with a green ensemble (still no pants though), but eventually decided that the shirt wasn't needed.

Purple Rain is what officially catapulted Prince to mega-superstar status with its legendary songs and accompanying movie. It was also this era that people would forever begin associating Prince with the color purple. No other artist can claim purple as their identity now, and nobody will ever forget the many different variations of his glittery purple sequin jacket.

And even though Purple was his signature color, let's forget instances like these where he would bust out the red velvet. You know what? That's exactly what we're going to call this outfit—The Red Velvet.

Leave it to Prince to go in a completely different direction than expected. By the time 1986 rolled around, the then 28-year-old was far removed from his Purple Rain persona, making it clear that he didn’t want to get stuck in a cycle where he was doing the same thing over and over again. For his Parade tour and album, Prince took on a smooth, suave modern-day 1950s look, ditching his rockstar outfits for oversized suits, and switching the jerry curl to a slicked-back short haircut. 

The 1950s look, however, didn’t last very long, as Prince opted for a “nerdy rockstar” style to go along with the release of his newest album Sign ‘o’ The Times, which was released in 1987.

Fast forward to 1989, Prince was back to his long luscious waves and glittery outfits during the course of his Batman Soundtrack promotional campaign. He continued to sport a similar look in the year 1990, which also included him starring in the film Graffiti Bridge.

Ah, the good ole assless chaps. Everything about Prince’s performance at the 1991 VMA’s tested the limits of early 90s broadcast television. For starters, Prince was performing his hit single “Gett Off,” which is about… never mind you guys are gonna have to listen to it. The lyrics alone probably had the men in suits at the VMA headquarters wincing, and I’d have to imagine that their anxiety got even worse when they saw his stage set up and background (again you have to see for yourself).

If their blood pressure was already rising at the beginning of the performance, they probably had a full meltdown when Prince turned around and revealed his…bare butt cheeks. To this day, Prince’s costume is still talked about whenever classic VMA moments are revisited.

Sidenote: Take a look at the sign Prince flashes at the end of this performance. Wild.

I’m including this because the year 1993 for Prince was a transformative one—not just in style but personally and professionally as well. During this time, Prince began going by an unpronounceable symbol (which was a blend of the male and female gender signs) that would often be worn on his clothes, in the background of his performances, and branded on his albums. You see, it was this era where Prince began battling his record label Warner Bros. for the rights to his masters. As such, Prince quit going by the name “Prince,” and began only using the unpronounceable symbol.

However, since the symbol was unpronounceable, if you were talking about him, let's just say on tv, you would have to refer to him as “The Artist Formerly Known As Prince.” The symbol stuck with Prince for the remainder of his life (even after he went back to using his name) and in the years since his fans have started using the symbol in their profile pictures, have had it tattooed onto them, and have essentially made it their own too.

You know how it is when you’re going through a rough time—you cut all of your hair off. That’s exactly what Prince did in the mid-1990s when he chopped the bouffant he had been rocking the previous year, into a shortcut with a bang. His style also became noticeably darker, with the incorporation of a lot of black into his wardrobe. Prince would pretty much keep slightly different variations of this look for the next four years, even dying it a lighter brown color in 1997.

Because only Prince would show up to a basketball game with an all-glitter top, matching trousers, matching boots, and a pimp cane.

Whenever anyone talks about Prince’s best style moments, this is always included. I’m not sure how exactly to describe this other than angelic. Only Prince could pull off a fit like this, and the response of the crowd still proved the power that he possessed more than twenty years into his career.

In my opinion, Prince did an excellent job maturing his style. It was still very “Prince,” and very “Rockstar,” but at no point did it look like he was trying to hold onto the younger variations of himself. The sharp suits and short cut were a very smooth look.

In what may or may not be ironic, Prince ended his life fashion-wise the same way he started—with a 1970s afro and bohemian style, which was similar to how he looked when he released his debut album For You in 1978. Life truly is full circle.