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    16 Pics Of Madonna's Fashion Evolution Over The Years

    Madonna is celebrated as a fashion icon; she's daring, she's adventurous, and she's not afraid to try out things, things that most of us would never be caught dead wearing. This approach to her clothing makes Madonna well-respected in the industry, and more often than not, her bold style pays off and she ends up looking fashion-forward and chic. She's the sort of woman who sets trends, not follows them, but fashion fails happen to the best of us.

    When you are constantly in the public eye and have attended more red carpet events than you can count, there are going to be times that you get it wrong. And when Madonna gets it wrong, she really gets it wrong! There are times when she's thought it was perfectly OK to let her lacy undergarments or lady bits hang out (it's amazing to think she's actually a mom of six), and then there are times when she has opted to dress down in oversized tracksuits and baggy clothing which made her look as though she picked them out from the nearest garbage bin. And on that note, below are 16 times Madonna's clothing left a lot to be desired.

    16 When You Cross A Disco Queen And A Cowgirl You Get This

    Madonna is celebrated for being daring with her fashion and one thing you would never call the singer is a wallflower, but sometimes she takes things way too far with her outfit and ends up looking awful, or like a Christmas bauble.

    The singer wore this bejeweled red trouser and top combination to MTV's EMAs in 2000, and it's so busy that you don't even know where to look -- although that gigantic M just below her belt buckle certainly suggests that's the spot where Queen of Pop would like to draw your attention to. The outfit cheaply made and the heavily embellished sleeves look as though they'll catch on everything.

    Of all the outfits that Madonna has worn over the years, this combination of cowgirl meets disco queen is probably the one she wishes she could forget.

    15 Madge, Michael Jackson Wants His Gloves Back

    I don't think red is Madonna's color, but that's not what's wrong with this outfit, what it is those awful black gloves (only Michael Jackson can pull off the gloves). Madonna wore this outfit in 2017 while promoting her line of skincare products, MDNA SKIN, at Barneys New York.

    The Roland Mouret 'Ardingly' dress is a flattering fit and is very feminine, plus it hugs Madonna's curves in all the right places, but the way she chose to accessorize her look is over the top. The gloves, the multi-colored bracelets, and the oversized sunglasses make our eyes hurt. Some will argue she looks chic and fashion-forward (they clearly need to get their eyes checked), others will agree that she looks as though she's trying too hard, and Madonna definitely doesn't have to try to impress.

    14 Her Met Gala Getup Was Hillbilly Chic

    Why would anyone wear camouflage unless they are a) in the military, or b) a hunter. Madonna is neither (that I know of) so it was annoying when she showed up at the 2017 Met Gala wearing this. What this is, is a full-length Jeremy Scott-designed Moschino gown complete with a utility belt and a heck of a lot of pockets. She completed the look with heavy metallic accessories, and gloves, again.

    One thing this dress does is attract attention, and the Met Gala is definitely the fashion event of the year, but is this really the sort of attention you want to be attracting? We know from the previous year's Met Gala getup that dressing for the ball is not exactly Madonna's strength because she likes to be daring but then takes it too far.

    13 Madonna Was Trying To Channel A Gothic Lara Craft

    There is definitely a line between showing enough skin to look fashionable and feminine, and then showing off so much skin that it comes across as tacky. Most of us try to adhere to this fashion rule, but at times, that line is completely invisible to Madonna, and she does whatever the heck she wants.

    In 2016, she stepped onto the red carpet of the Met Gala wearing an outfit that looks as though it was inspired by the love child of Lara Croft from Tomb Raider and a goth. The Met Gala is an event that is known for its out-there fashion, and considering the theme was Manus x Machina: Fashion In An Age Of Technology, celebs got really creative with it. However, it didn't look as though this Givenchy creation was a good fit for Madonna, and it left little to the imagination.

    12 If Only She'd Said 'No' To This Awful Outfit

    Unless you're a school girl or a ballerina, this is never going to be a good look, then again, Madonna is known for her controversial antics and it was no doubt her intention to cause shock and awe when she stepped out looking like a schoolgirl with this outfit.

    This what was Madonna wore to Cannes Film Festival in France back in 1991 (when she was aged 31, so definitely not anywhere close to a school girl). Designer Jean-Paul Gaultier, who Madonna has a great relationship with, created the white and black tutu, which she paired with thigh-high white stockings and a gray blazer. But her outfit choice at the time was not that shocking considering Madonna had previously proven she was a big fan of tutus when she wore one in 1987 film, Who's That Girl.

    11 This Happens When Christmas Is Your Favorite Time Of The Year

    When people say you should “go natural,” they don't mean attend an event looking like you've pulled out your lawn and transformed it into a dress, but it seems Madonna didn't get this memo. In 2008, when she rocked up at Gucci's launch of the Tattoo Heart Collection at New York City's Plaza Hotel, she did so wearing this dress. This dress is surprisingly not a Gucci creation (which is pretty nervy), instead, Madonna arrived wearing head-to-toe Louis Vuitton from the brand's Spring 2009 collection. And oh, do we wish she didn't because she looks like a Christmas tree thanks to all those green feathers.

    The aim of the Gucci Campaign was to Benefit UNICEF, so Madonna wore this piece for a good cause, but unfortunately, there is nothing good about this outfit.

    10 Madonna Was Into Athleisure Before It Was Cool (And It Wasn't)

    If you want everyone to know you're the biggest star in pop, you don't wear this.

    The positive about this look is it's actually affordable because it was designed by high street retailer H&M, but there is nothing remarkable about it. This was reportedly a collaboration between the singer and the brand, but it was one that was not loved by the general public, and according to PopSugar, despite a lot of advertising, this tracksuit failed to impress.

    It was reported that no one was buying the outfit, and after three months of them being on the racks, the retailer was forced to reduce the cost in hopes of boosting sales. In addition this report, they are also claiming that H&M even resorted to giving away some of these tracksuits on their Myspace page!

    9 When You Try To Tone Down Your Look, But You're Madonna

    Madonna doesn't know what toned down means, I say this because she either goes all out (and more often than not this works for her), or she goes super casual and ends up looking sloppy. This outfit is definitely one of those that grabs attention, but then again, when have we known Madonna to not want all eyes on her?

    She rocked this jacquard pantsuit by Gucci when she attended Billboard Women in Music 2016, and although the fabric is bright and bold, the fit of the suit actually works for Madonna. Here's what doesn't work; the awful glitzy accessories. Someone thought it would be a good idea to complete an already out-there look with bold accessories, including gold earrings, bracelets, and then an oversized gold bow necklace. Ugh!

    8  Unfortunately Coral Is NOT Madge's Color

    You may look at this outfit and think that it doesn't deserve criticism, and maybe you're right in some ways because the actual style of the stress (minus the neckline) is pretty great, the color, well, not so much!

    This coral hue is bright and bold, so it's right down Madonna's alley, but it's a color she should definitely avoid because it makes her look so pale and washed out. The shoes do nothing for her, and then there's the fact that the dress' fabric looks clingy, and when she does this pose, it really strains on her arms. But the absolute worst thing about this dress is that neckline! It looks like something a woman twenty years older than her would wear, and what the heck is happening with that bow? Dreadful.

    7 We Are Drawn To This Outfit, Like A Moth To A Flame

    Remember back to when you were a kid and your mom told you to hold your tongue if you didn't have anything nice to say? This is one of those times, the difference is I'm now an adult and have become a lot more opinionated when it comes to people's clothing than I should be. Also, it's hard to hold your tongue when you see this Vionnet gown, which Madonna wore to the Venice Film Festival while promoting her film W.E.

    Giving credit where credit is due, the style and the color of the gown are a win and the pale gray looks really great on Madonna, but the red butterfly details are not only a color clash but also an eyesore. She chose to play into the red accents by pairing the look with red sunglasses (it looks as though this photo was taken at night) and red gems. Well, at least she left the gloves at home.

    6 I Know This Is The 80s, But My Eyes Hurt

    Madonna rose to popularity in a big way in the '80s and her looks were bold and ever-changing. This is the period which set her apart from the rest and made her a fashion icon, but almost four decades later we look back at the '80s and wish we had sunglasses to protect our eyes from the fluorescent shades.

    This was a time that focused on colorful, eclectic garments, so we have to partly forgive Madonna for this outfit because we can blame it on the decade, but there is just so much going on in this image that we have to comment on it. The studs, the gloves, the yellow nail polish, and the beaded rosaries and peace sign are things that you would never wear together (and you can see why. And then her outfit has a combination of mesh as well as lace which makes it far too textured.

    5 Flashing Your Lacy Undergarments Is Not Advisable

    If you've got it, flaunt it, right? Well, that statement may be true most times but there is a difference between showing off your assets and letting them hang out all over the place, and the latter is definitely not advisable. If only Madonna understood this because there has been more than one occasion when she has shown off her lacy undergarments, and now that she's a mother of six, she'd do well to tone it down a bit.

    Putting her lack of modesty aside for a hot minute, it's not just the bra that's a problem; a corset may be a style that Madonna looks good in but combined with the out-dated skirt, it just doesn't work. And then there are those lace-up shoes, which make us think of Kim Kardashian's bloated feet during her first pregnancy. No, just no!

    4 Oversized Clothing Is Never Flattering

    No one wants to travel in clothing that's uncomfortable, especially when it's a long haul trip, so you can understand why Madonna wanted to dress down and wear something she would feel relaxed in. The problem is that her outfit has crossed the line of casual, and has become sloppy and unflattering.

    Another reason for her baggy clothing, scarf, and hoodie, could be because she didn't want people to recognize her at JFK airport, and was hoping that if she wasn't showing skin (which is characteristically Madonna) then she could fly under the radar. That's never going to work because fans can always spot their idols from miles away, and the second reason why it didn't work is that all eyes would be drawn to her because of her awful outfit.

    3 It Looks Like The Designer Just Crumpled Some Fabric

    There have been times when Madonna has taken a break from her grunge style and ditched the leather, the black lace, and the gloves in favor of something a little more glamorous. This is one of those times.

    When Madonna attended the Vanity Fair Oscar Party at Morton's in West Hollywood back in 2006, she wanted to wear something that was uncharacteristic, and she ended up choosing a pink Versace dress, which is too reserved for her. Not only that, the ruffles on the dress look as though the designer took a piece of material and just crumpled it a bit, then gave it to Madonna to wear.

    When you see this pink dress, you have to wish she didn't ditch her usual getup in favor of it, but at least her jewelry is nice.

    2 This Would Be Cute, If It Was The 1920's

    When I look at this outfit it reminds me of something someone on the set of The Great Gatsby would be wearing, and if Madonna was wearing it on the red carpet in the 1920s, then it would actually be a pretty cute look. Unfortunately for her, she's just a few decades late.

    This was the outfit that Madge wore to the premiere of I'm Going To Tell You a Secret, a documentary of her world tour in October 2005. The pants are flattering and we know Madonna is a fan of black so it's in keeping with her usual style, but then she decided to pair these pants with awful gold shoes, a headband that would be at home on a flapper, and a sequin hoodie (unless it's Christmas time, sequins should be left at home).

    1 What Is This Look, Bag Lady Chic?

    There is so much wrong with this look, and even though it's designer clothing it just looks tacky because of all of the layering. Layering is great for cold weather or transitional dressing, but it's not so great when you throw on oversized pieces that look as though they've come out of the garbage bin.

    This photo was snapped when Madonna walked the streets of New York City in 2016, and people really loved her choice of bag, which happens to be Gucci's Dionysus bag, but that's probably where the love stops. Although her asymmetrical cropped jacket is cute, in combination with leather shoes, a dress, and stockings, it's all just a bit too much and she looks as though she belongs in a dungeon rather than at a fashion show. Sorry, Madge!