Cher Outfits That Hit All The Wrong Notes

Cher is nothing short of an icon. Over the course of her career, which has spanned six decades as of this writing, she has proven that she is the epitome of star power. The singer, of course, has famous vocal chops and seemingly endless stage presence. Beyond this, though, she is nothing short of a fashion icon and has managed to look stunning and set trends for nearly 60 years. That doesn't mean, however, that every outfit she's sported over the years has been a winner.

Cher has rocked many daring outfits and worn red-carpet dresses that left little to the imagination. Of course, with fashion risks come hits and serious misses. And, while in many ways, Cher doesn't seem like the average human, she occasionally has a style misfire just like the rest of us. In Cher's defense, most stars have had way more fashion fails in over five decades than just five. Even so, a weird outfit is a weird outfit. And, from totally baffling jeans to a clown-inspired red carpet look, Cher has had a few. So, here are some of Cher's worst looks over the years, because even the stars with seemingly flawless fashion have an occasional flop.

Are we amazed by Cher's youthful vibes in this ensemble that she sported at the "Bob Mackie: Naked Illusion" premiere in May 2024? Absolutely. Does that mean it's one of her best outfits? Absolutely not. Cher loves a daring, out-there look, and we love her for it, yet sometimes adding too many surprising elements to an ensemble can cause the outfit to get in its own way. That's definitely the case with this look. With cutouts, different fabrics, and layers, this outfit just gave us so much to look at. 

Sure — we can see the vision here. There's something about it that reminds us of a vintage superhero, Maleficent, an '80s rockstar, or some combination of the three. Unfortunately, we have no idea where to look. Removing the draping on the belt area and the jacket may have given us a chance to really understand what was going on in this outfit. As it is, though, it just looks like she grabbed too many pieces from the costume closet. 

In her early years, Cher was already the queen of iconic ensembles. She took fashion risks, and almost all of them paid off and somehow manage to still look fashion-forward today. In 1991, however, she sported a bold ensemble to the MTV Awards that just doesn't quite work. The look appears to be a pair of sheer and opaque black striped tights with a black corset and a thick matching belt. She paired this already busy look with mid-calf boots, a long purple jacket, and a big, curly red wig. 

All in all, this ensemble just had way too many details, and it left Cher looking overpowered, which of course, isn't easy for a look to do. And, we can't ignore that the whole ensemble has total circus vibes, and Cher would look so much less out-of-place if she was doing a trapeze performance under a tent than walking the red carpet. 

Back in 2002, Cher headed to the VH1 Divas event in a look that still confuses us to this day. Jeans are certainly a casual choice compared to Cher's typical style. Yet, these jeans are just plain bad. They have fraying at the hem and what appear to be faux leather inserts in abstract shapes on the thighs. Worst of all is a turquoise belt pointing downwards by her crotch. While we're not sure exactly what it may be, these jeans and how they are styled are clearly meant to make a statement. This makes it even stranger that the top half of her body felt more like a boring, everyday early 2000s getup.

Cher paired her wild jeans with an odd leopard print top, a heavy, layered necklace, and a choppy blonde wig. All of these details caught this outfit somewhere between a look someone might wear for a day out shopping and a major statement, leaving the whole thing confused.

In 2013, Cher headed to "The Late Show with David Letterman" in what would turn out to be one of her worst outfits of the decade. While that may be a strong way to put it, this getup is, in fact, particularly bad. From her worst looks to her best, no matter how wild one of Cher's ensembles appears, she seems consistently deliberate in her choices. Her looks often make statements, but that doesn't mean that they look disjointed, messy, or uninspired. This is where this particular look went wrong. She uncharacteristically piled many different pieces and accessories on top of each other, and the result was a mishmash of elements that just weren't cohesive. 

Cher wore what appeared to be leather leggings under a leather skirt. This already made for a heavy, overwhelming look, but she didn't stop there. She added clunky boots, a complicated gold belt, a printed blazer, and a multicolor scarf that totally clashed with all the other vibes she had going on in her outfit. This was all enough to make for a distracting look, but her hair, which appeared to be a layered platinum blonde wig, just added even more detail and distraction. 

Throughout her many eras, many different decades in showbiz, and many elaborate ensembles, few elicit the response: "What the heck is going on here?" In 2002, however, Cher attended the 29th American Music Awards in a complicated jeans and vest look, and all we can say is... what the heck is going on here?

Jeans and a black top make for one of — if not the — most classic outfit formulas of modern times, so we're not quite sure how Cher managed to go so awry. Perhaps it's because casual-wear simply isn't her style. The star sported light-wash jeans with black crosses printed all over them. She paired them with a distressed, off-the-shoulder black top, a busy-looking grey vest, and what appeared to be multiple different waist chains. This look just overwhelmed the star with gaudy, costumey details, and she just didn't quite look like the superstar she is in such a confusing look.