Grammy Awards: Worst/Best dressed!

It's that time of year again! When music's biggest and most talented stars flock down the red carpet wearing wild takes on high fashion. In many ways, the Grammy's is the most entertaining of the award shows because it takes expressive individuals and asks them to dress nicely. That always results in a healthy amount of awesomely confusing looks! Here are my picks for the worst best dressed of the Grammy Awards! I mean, we all can agree right - when it comes to the Grammy Awards, we prefer strange!

ariana grande, aldo, grammy awards 2014
Ariana Grande in Aldo

Now that Katy Perry has left her kitschy side behind, I'm happy to see Ariana Grande continue in her wake. First, I've never seen Aldo on the red carpet. So that's worth a mention - this was customized for Ariana. But she's wearing flesh tone panty hose. That always ruins a look for me! Come on girl, it's not 1990. I do find her level of cute is starting to weigh heavily on me. I'd really love to see Ariana rock an edgy, or at least normal (for a change), look.

We all know where this goody two-shoes act is going right... (See Lohan, Miley, etc.)

cyndi lauper, alexander mcqueen, 2014 grammy awards
Cyndi Lauper in Alexander McQueen

When I say the worst is actually the best when it comes to the Grammy Awards: see Cyndi Lauper. Short of the hair, this is really working for me. Sure it's over-the-top and costume-y, but that's perfect for the Grammy's. Cyndi's hair looks like a Disney Princess Ariel wig after a few rounds in the dishwasher. But I love how stately and regal this Alexander McQueen is, albeit in a very campy way. Lauper's a true icon and I find it appropriate she came with a cape.

katy perry, valentino, grammy awards
Katy Perry in Valentino

When this gown opened Valentino SS 2014 Couture in Paris last week, I thought it had Katy Perry at the Grammy's all over it. Sure enough, here she is. I debated between putting this on the worst and the best dressed list for some time, but put it here because I think it was such an obvious choice. If Perry wants to mix up her image, she needs to reinvent herself but not making the obvious choices. And a cutsey, musical print at the Grammy's isn't exactly setting off in a new direction.

Also, and this is not Perry's fault, I loathe the wings that come on the shoulders and wrists of this. I'm not a fan of tulle and this gown takes tulle too far. When I think of couture, notably Valentino couture, I think of fine fine craftsmanship and this one seems very thrown together and sloppy to me. (Although I'm sure everyone else would completely disagree with me.) Let's just say, I love to hate this! ;)

madonna, ralph lauren, grammy awards
Madonna in Ralph Lauren

I love this! Madonna takes herself so seriously and I never tire of it. She looks like she's the ring leader of the big event. And really, she kind of is. It's the Grammy Awards and that's Madonna's stomping gown. Madonna brought her son with her as a date, and they both wore head to toe Ralph Lauren - cane included. In her red carpet interview, you also realize that Madonna is sporting a Grill. Yes, an actual grill. This is over-the-top perfection.

sara bareilles, bluemarine, grammy awards 2014
Sara Bareilles in Bluemarine

This final look on Sara Bareilles isn't a worst-but-actually-best-look. Nay, it's full on worst. Can we officially retire the mullet dress? Please! Especially ones that look like they were tarred and feathered. Suddenly I'm having visions of that dining room Home Alone scene where Kevin adorably fanned down feathers all over the burglars. Great movie and scene, not a great fashion moment.

Contributor: Kelly Lund