Rihanna has us questioning her judgment these days, and no, we're not (just) referring to alleged hook-ups with Chris Brown. We saw her this week in boots that had us wondering if her legs had been swallowed by boa constrictors, and silk pajamas that were one sneeze away from a wardrobe malfunction.

Elsewhere, we saw Gwen Stefani stepping out in something just plain kooky. Check out those over-the-top looks, as well as more celebrities who made our week's worst-dressed list. Let us know if you agree or disagree with us, then head over to our best-dressed gallery to rest your eyes on this week's style winners.

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  • Madonna

    Umm, OK. There's fur, garters, fishnet stockings and a really exposed bikini line. Which part of that says, "Hey, let's hit a red carpet!" Las Vegas, May 19th Photo Credit: Getty Images

  • Ke$ha

    Oh, hey Ke$ha's rear end. Showing off this much skin is brave, but it's also tacky. If you're going to dare to bare, then reveal an inch or so of your midriff with high-waisted bottoms. That's enough allure. Las Vegas, May 19th Photo Credit: Getty Images

  • Marion Cotillard

    This dress seems to be leaking. The hem can't decide whether it's short, long or in-between and it distracts from the French actress' beautiful face. Cannes, May 17th Photo Credit: Getty Images

  • Alyssa Milano and Avril Lavigne

    Alyssa's outfit is straight out of "The Golden Girls." She didn't need the transparent palazzo pants; the dress would've been perfect. A leather dress is a tricky endeavor. Go for a simple silhouette if you're going to try it, and stick to neutral accessories.  Las Vegas, May 19th Photo Credit: Getty Images

  • Alessandra Ambrosio

    The Victoria's Secret model looks like she's being choked by chiffon. New York City, May 20th Photo Credit: Getty Images

  • Carly Rae Jepsen

    A belly-button sighting is nothing new. But what is dragging behind her? Whatever that is, it's distracting. Las Vegas, May 19th Photo Credit: Getty Images

  • Melissa George

    A leather bra is OK ... if you're en route to an S&M function. If you're going to show off that much skin, well, you should be at the beach. New York City, May 15th Photo Credit: WireImage

  • Eva Longoria

    If you're going to choose a neutral shade, choose one that complements your skin tone. This fleshy hue looks like the "Desperate Housewives" actress is in a full body cast. Cannes, May 17th Photo Credit: WireImage

  • Irina Shayk

    A plunging neckline and sheer material is just cheap looking. Especially for a red carpet. Cannes, May 22nd Photo Credit: WireImage

  • Jenny McCarthy

    Upon first glance, we thought we were looking at Ke$ha. A belly button-baring outfit is really only suitable for spring break. Add a ripped skirt and sky-high boots and we are scratching our heads. Las Vegas, May 19th Photo Credit: Getty Images

  • Kathy Griffin

    We are going to make a bold, blanket statement and say that wearing feathers can be very dangerous -- the furry detail skews silly on the red carpet. Beverly Hills, May 18th Photo Credit: Getty Images

  • Tara Reid

    Here's the deal: If you're going to go for a really short hemline, go for full coverage on top. Otherwise, you're headed to another word to tacky territory, especially when bows are involved. Los Angeles, May 21st Photo Credit: Getty Images

  • Nicki Minaj

    We will never, ever, ever support furry footwear. Ever. Los Angeles, May 16th Photo Credit: WireImage

  • Natasha Bedingfield

    This outfit has us wondering if the singer put on a risqué outfit, then had second thoughts and threw on a blanket to offer some coverage. If you're going to go sheer, beware. Los Angeles, May 18th Photo Credit: WireImage

  • Milla Jovovich

    A large-scale pattern doesn't do anyone any favors, especially when it's on a maxi-dress. It has the effect of making everything look ... maxi. Moreover, you know how important it is to emphasize the waist! Ugh, no. Cannes, May 19th Photo Credit: FlimMagic

  • Eva Longoria

    Once you start to wonder if that's a case of chicken pox all over the "Desperate Housewives" chest, you really can't look away. Paris, May 13th Photo Credit: FilmMagic

  • Anne Hathaway

    The curved sleeves on this dress are over the top. They remind us of gills. New York City, May 8th Photo Credit: Getty Images

  • Kerry Washington

    The "Peeples" actress has us scratching our heads. Why is she wearing her nightie on the red carpet? Los Angeles, May 8th Photo Credit: WireImage

  • Mariska Hargitay

    What do we need to say here? The "Law & Order: SVU" actress looks like she has a full diaper perched on her back. New York City, May 9th Photo Credit: WireImage

  • Jada Pinkett Smith

    We love menswear-inspired fashion on women. However, when there is shiny material involved, the look quickly takes a turn for the cheap. Los Angeles, May 9th Photo Credit: WireImage

  • Debra Messing

    The "Smash" actress' look is a lesson that wide-leg pants should be worn with caution. The volume in these pants adds width in unintended places. New York City, May 9th Photo Credit: Getty Images

  • Michelle Trachtenberg

    One of the style tenets that we always observe is to emphasize your waist. So you can imagine our disappointment upon spotting the actress in this blousy maxidress. Moreover, Trachtenberg added red carpet accessories to a dress that looked better suited for a day at the beach. Color us confused. Los Angeles, May 9th Photo Credit: Getty Images

  • Diane Keaton

    Leather and fishnet stockings are not what we expected on the "Annie Hall" icon. Then, throw a bowler hat into the mix and we really don't get what's going on. Los Angeles, May 10th Photo Credit: Getty Images

  • Demi Lovato

    Shiny leggings are totally cool ... if it's 1980 and you're on a pair of roller skates. A simple pair of skinny jeans or leather pants would've done nicely here. Los Angeles, May 11th Photo Credit: Getty Images

  • Avril Lavigne

    Shiny leggings are never OK, especially when paired with a sequined vest. Los Angeles, May 11th Photo Credit: FilmMagic

  • Chloe Sevigny

    The actress is wearing a dress with a serious split personality. The frock really can't decide if it's going to yoga (hello, Spandex!) or to a bohemian-themed soirée. New York City, May 13th Photo Credit: Getty Images

  • Minka Kelly

    There's a vine crawling up the actress' crotch, for starters. Once you've seen that, you can't un-see it. New York City, May 13th Photo Credit: WireImage

  • Lauren Graham

    The "Parenthood" actress took a serious style misstep in this tea-length dress. The longer hemline tends to have a shortening effect, especially when paired with shoe booties. A knee-length hem and strappy stilettos would have been aces. New York City, May 13th Photo Credit: Getty Images

  • Zoe Saldana

    The actress is usually on our <em>other</em> list, but this look is a fail. The color falls flat against her skin tone and the chiffon looks like a flimsy nightie. We are just glad that she lined the bottom half of the dress. Los Angeles, May 14th Photo Credit: Getty Images

  • Diane Kruger

    The German actress seems to be missing something ... about a foot of material in the mid-section of her top. Cropped tops are back, no doubt, but in a classy, '50s-style way where only an inch or so of skin is exposed. Los Angeles, May 13th Photo Credit: Getty Images for MAC Cosmetics

  • Phoebe Price

    We can always count on the actress to bring a healthy dose of questionable style to the red carpet. This gown clearly doesn't offer her any support, since it's sagging and heading into wardrobe-malfunction territory. The floral pattern would be OK on a flirty summer dress, but here it comes off looking like grandma's couch. Lastly, those accessories were a poor choice and the tiara is overkill. Cannes, May 15th Photo Credit: WireImage

  • Florence Welch

    Someone just stepped out of their boudoir and forgot to take off her dressing gown. The lesson here is to be very wary of pink satin. And absolutely steer clear if polka dots are involved. Cannes, May 15th Photo Credit: WireImage

  • Paz Vega

    A leotard with a crochet scarf on top is not what we expect to see on a red carpet. Cannes, May 15th Photo Credit: WireImage

  • Mia Moretti

    Pattern-clashing is a big trend right now and there are a few stars who do it really well (think: Solange Knowles). The key is to choose a really simple silhouette -- a slim pair of pants and a classic blouse work well -- and keep the rest of your look really neutral. The DJ layered so many prints and patterns that the outfit became a morass of fabric. The heavy accessories are distracting. New York, May 15th Photo Credit: Getty Images

  • Rihanna

    If you consider walking out of the house with your belly-button exposed, repeat this mantra, "It is not Spring Break and I am not 16." New York City, May 15th Photo Credit: Fame Flynet

  • Katy Perry

    Perry looks like a cartoon in this rose-adorned gown. Between the throne, bouquet in her hand and all the royal paraphernalia surrounding her, the dress is just another prop for the pop star. New York City, May 2nd Photo Credit: WireImage

  • Paloma Faith

    If you're going to experiment with outrageous details (sequins! Opera-length gloves! A fascinator!), then it's smart to choose one accessory and keep the rest of the outfit as minimal as possible. New York City, May 6th Photo Credit: Getty Images

  • Nicole 'Coco' Austin

    Where to start? It's one thing to emphasize your best assets (which we highly recommend), but on a red carpet it's important to stick to a certain dress code that is generally <em>not</em> short and tight. Las Vegas, May 4th Photo Credit: WireImage

  • Bjork

    The Icelandic singer is known for her quirky style, and this is no exception. Bright leggings and a floral dress are bound to clash, but throw an olive-colored poncho on top and you've got a clothing catastrophe on your hands. New York City, May 6th Photo Credit: Pacific Coast News

  • Kylie Minogue

    Wearing patterns from head to toe is a big trend this spring, but there are guidelines to follow, unless outlandish is the look you're attempting. It's imperative that you keep the silhouette classic and simple. Minogue's bell sleeves make her outfit look over-the-top. New York City, May 5th Photo Credit: Getty Images

  • Ashley Greene

    We are really struggling with the fit of this gown. The dramatic bust line, coupled with the overly voluminous skirt (what is under there?) makes for a costume-y look that overwhelms the pretty actress. New York City, May 6th Photo Credit: Getty Images

  • Rihanna

    The pop star evidently didn't get the memo that it's no longer 1995 and it's not OK to tie up your sweatpants and wear them out in public. Though really, when was it ever appropriate to do that? New York City, May 7th Photo Credit: WireImage

  • Julianne Hough

    A below-the-knee hemline is tricky territory for the diminutive celebrity. Moreover, the gathered fabric at her waist comes off as wrinkled and sloppy, and the shiny fabric looks like it could be highly flammable. Los Angeles, May 2nd Photo Credit: FilmMagic

  • Sue Wong

    Feathers are a daring style choice. But when paired with a top hat and off-the-shoulder gown, the outfit becomes comical. Los Angeles, May 3rd Photo Credit: WireImage

  • Kylie Minogue

    Exercise caution when wearing stripes. A bateau-neck T-shirt is perfect, but when it comes to dresses, stick to thin stripes for the most flattering effect. New York City, May 4th Photo Credit: Getty Images

  • Valerie Simpson

    Hats are de rigueur at the Kentucky Derby. But when wearing a large headpiece, it's important to keep the rest of the outfit minimal, since the hat will be the center of conversation. This particular look is having several conversations at once, and we can barely make sense of it all. Louisville, May 4th Photo Credit: WireImage

  • Eve

    The rapper's bizarre neckline has us scratching our heads. New York City, May 5th Photo Credit: Getty Images

  • Solange Knowles

    Wide stripes, a plunging neckline, a peplum and red shoes all add up to a very busy outfit. Solange is normally the queen of pattern clashing, but all the different aspects of this look have us bewildered. One issue is that the deep V meets the stripes at the singer's middle and diminishes any notion of a waist. New York City, May 5th Photo Credit: Getty Images

  • Alice Eve

    We have mad love for an illusion neckline, but this outfit has us wondering if the actress realized a little too late that her top was transparent, grabbed her sports bra and headed out the door. If you're going to try the see-through trend, make sure your underthings are pretty and offer full coverage. Mexico City, May 7th Photo Credit: WireImage

  • Vanessa Hudgens

    The "Spring Breakers" star loves a bohemian vibe. But between the patterned pants, crop top and fringed bag, it's overload. A chambray shirt would have toned this outfit down a notch. Los Angeles, May 3rd Photo Credit: Pacific Coast News

  • Rihanna

    Oh, RiRi. Didn't we all learn from Anne Hathaway's turn in these boots? If you're going to dare to wear outrageous footwear, then you have to keep the rest of your outfit bland so that the elements aren't fighting each other. New York City, April 30th Photo Credit: FilmMagic

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