5 Worst Dressed Celebrities

There are some celebrities that look amazingly put together whenever they step outside, carrying off any style with elegance and grace. And then … there are those celebrities that don’t!

Instead of focusing on the red carpet events, I chose to pick the celebrities as they go casual. Because then you can’t really blame their stylist!

Here are my top five worst dressed celebrities:

Kim Kardashian recently found herself on the Grammy Awards worst dressed list, but I think Kim fails when it comes to casual wear as well. She and Kourtney were spotted getting their nails done in Beverly Hills earlier this year and Kim’s shirt didn’t quite cover her leggings. She has to keep pulling it down, and I don’t even want to know what the view from behind looked like! Maybe the outfit looks better with those boots she’s carrying, but somehow I doubt it.

Amy Winehouse is always a train wreck, so it’s no surprise that her wardrobe leaves us cringing! What can I say about this particular outfit, other than it looks like she yanked most of the items from a poor, unsuspecting, homeless person. And her headwear keeps reminding me of I Love Lucy. The only thing she has going for her are those brand new ballet slippers that she picked up that very day, and they’re already starting to look trashed.

Courtney Love is another one of those celebs who finds herself on every worst dressed list imaginable! Whether she’s heading to the red carpet or headed to the store, Courtney just can’t seem to get it right. Perhaps that’s what we love about her? I happen to particularly love this ensemble. The purple crown makes me think she’s headed off to Chuck E. Cheese!

Mary Kate Olsen can be oh-so-adorable when she wants to be. But she only gets it right about half of the time! I’m not sure what is up with this dress, but she lost her neck. I think she forgot the shoulder pads went down with the 80s – and these ones look like they belong on a football player.

Lindsay Lohan was spotted leaving Samantha Ronson’s house earlier this year in an outfit that makes me cringe! Lindsay has also made her fair share of worst dressed lists, and I have to admit to being sick of seeing her in black leggings and baggy shirts. And honestly – that jean vest has to go! I realize the 80s are coming back in style, but this is about as unflattering as it gets.

Images Credited to INF, splashnewsonline.com, and Bauer Griffin