Everyone makes poor fashion decisions sometimes. Most of us can safely say that we’re guilty of having worn something ugly or unflattering, either out of laziness or in an attempt to try something different or new. But this is a list of celebrities who demonstrate consistently awful fashion sense. It does not include stars like Lady Gaga, Nicki Minaj, and Lil’ Kim, whose outfits, though generally terrible, are clearly intended to be subversive and daring. When Nicki Minaj dresses like a Lolita-esque space alien, she’s clearly trying to attract attention, positive or negative. The worst dressed celebrities on this list are people who seem to think they’re well-dressed, or in the case of Charlie Sheen, are just inexcusable slobs. Money can’t buy taste!
Jessica Simpson is one of those people who’s rolling in money, and yet somehow still manages to look like she bought all her clothes at Sears. The boot-cut, acid-wash jeans, the sequins, the pairing of boots with shorts… why, Jessica, why? You’re so gorgeous and you have so much money. You could do better! On the other hand, Jessica Simpson is a country singer from Texas, so her style is predictably country. If you fit that demographic, maybe she’s well-dressed to your eyes. But for the rest of us, it’s not a good look.
Jessica Simpson is an interesting case. She walks the line between Christian country-bumpkin “good girl” and bodacious, bosom-bearing starlet. Jessica grew up in a Christian household and was given a purity ring by her father at the age of 13. She’s also a Republican and endorsed president George W. Bush in 2004. On the other hand, she has received considerable criticism from some country fans and stars, particularly those in the Christian country music sector, for her sexy image and provocative modeling. In my opinion, it makes no difference if you’re a sexy bombshell or a virginal Christian—both are valid choices. But wearing a crocheted poncho when you’re under the age of 40? That’s unforgivable.