Michelle Pfeiffer Hasn't Had The Easiest Ride To Becoming A Fashion Icon

Michelle Pfeiffer has been a staple in Hollywood for decades now. She's seen the ups and downs of plenty of fashion trends, but that doesn't mean she always had a grasp on what was in and out. Nowadays, she's an undeniable fashion icon with a chic and sophisticated style, and she shows it off whenever she attends a promotional event or red carpet. But that wasn't always the case. While Pfeiffer was making her name in the entertainment industry, and even as a successful star, she's participated in a few fashion faux pas, just like anyone else. 

From her first credited role in "Fantasy Island" in the late 1970s to now, Pfeiffer has tried out a slew of style fads. Some worked out, while some were major fails. This included interesting headwear, bold patterns, and odd-fitting outfits. Meanwhile, Pfeiffer has worn some pretty iconic outfits on screen. This includes her "Batman Returns" catsuit, her sharp bob and sleek dresses in "Scarface," and her Pink Lady attire — which might be the only thing she doesn't regret about her role in "Grease 2."

Through the good and the bad, there were plenty of memorable ensembles for Pfeiffer. Of course, even when her fashion was at its worst, she's still Pfeiffer. So she could usually pull it off no matter how bad it was. But we can't deny that it took her quite some time to develop her stunning personal style. Here's a peek at some of her worst fashion moments over the years before she truly earned her style icon status. 

For the premiere of Martin Scorsese's 1993 adaptation of "The Age of Innocence," the book by Edith Wharton, Michelle Pfeiffer wore an odd all-black outfit. It included a velvet beret with her hair tied back, paired with a long black skirt and structured jacket.

She also wore the jacket buttoned all the way up, adding to the severe look. While the ensemble fit well with the old-fashioned style of the movie, it was a strange choice for a high-profile movie premiere and felt out of place next to Scorsese's tuxedo. 

Another odd red carpet ensemble came a few years later when Michelle Pfeiffer attended the 1995 Emmys with her husband, David E. Kelley. They were there as a couple, but they definitely didn't consult with each other when getting dressed for the night.

Pfeiffer wore a light brown silk outfit, with loose pants and a long jacket top buttoned to her neck. The style didn't suit her very well, and she really blended in with everything around her while wearing the outfit. 

Another questionable ensemble was this 1997 look from Michelle Pfeiffer. With her partner David E. Kelley by her side, she attended a Fox event wearing what seemed to be a brown suit with a button-up shirt underneath that featured a green, white, and brown geometric pattern.

She completed the outfit with oval sunglasses with orange-tinted lenses. It seems safe to say that she was feeling inspired by '70s fashion. But this is a good example of why some styles should stay in the past. 

Michelle Pfeiffer and her husband, David E. Kelley, attended the premiere of "Cast Away" in 2000 in attire that finally felt coordinated. But even then, Pfeiffer's outfit was a bit of a miss. It seemed like she was trying her best not to stand out. 

Her tan dress featured a leafy pattern that sort of hinted at a tropical vibe, probably a reference to the setting of the movie. But unfortunately, it also looked like a curtain you might find in someone's house in the 1990s. 

In 2003, Michelle Pfeiffer was one of a bunch of celebrity guests at a special Rodeo Drive fashion event. For the occasion, she wore a black sparkling dress with spaghetti straps and a white floral pattern all over. 

While the idea of the dress was definitely fitting for the night out, the execution was another story. With the weight placement of the pattern and the random ruffled fabric on the neckline, the dress truly wore Pfeiffer, not the other way around. 

While attending the premiere of her film "Stardust" in Los Angeles, California, in 2007, Michelle Pfeiffer wore a navy blue sleeveless dress. It featured unique embellishments on the neckline and tiered ruffles down the entire garment.

She added a black clutch and black peep-toe heels to complete the outfit. But instead of looking like a movie star, the attire made Pfeiffer look like she was going to an office party or corporate conference. Probably not the effect she was going for. 

In 2012, Michelle Pfeiffer tried her hand at some popular trends with this sequined tank dress and strappy wedges. Let's just say, it wasn't her best look. 

The dress itself featured a strange pattern with pink, silver, and yellow colors, while she topped it off with a long chain necklace and a bunch of cuff bracelets. This is around the time that she started perfecting her style, but a few fails were bound to happen.

There's so much about this ensemble that could have gone right. But altogether, it was another story. Michelle Pfeiffer has always looked great in classy menswear-inspired attire, so a suit like this should have been a perfect fit.

But with the deep purple, the velvet pattern, and the dark floral shirt underneath, it had way too much going on. And the dark accessories also didn't help. Still, we'd love to see her give this suit another go if it was styled a little differently.