18 Most Difficult Outfits Jennifer Lopez Has Ever Had To Put On

In the age of stars like Kim Kardashian and Beyonce, there are plenty of female celebs who aren’t shy about flashing the flesh on the red carpet. We see it all the time. But aren’t we forgetting something? A certain beautiful Latina pop star perfected the art of (almost) baring all in public long before Kim K even made a name for herself, and her name was Jennifer Lopez.

Throughout the late 90’s and early noughties, no music event or awards bash would go by without us seeing some kind of outrageous new outfit from J-Lo, and at nearly 50 years old, she’s still flaunting her perfect pins, cleavage, and of course, her iconic bum to the world in impossibly-tight dresses. (She still looks amazing though, so fair play to her!)

Jenny from the block may have gone from “having a little to having a lot,” but she sure as hell wasn’t talking about clothing material! J-Lo’s eye-popping red carpet looks over the years have left very little to the imagination and can probably only be described as minimal at best. Lopez has an equally gorgeous and curvaceous figure, and she seems intent on showing it at every opportunity. Here are 20 times J-Lo was pretty much spilling out of her dress.

18 Strategic Cuts

Phew! Jen was really pushing the boat out with this cut-out dress in 2017. There are more holes in this risque red carpet gown than a kitchen colander! At last year’s Billboard Latin Music Awards, J-Lo decided to rock up in this sexy cut-out creation (or abomination, depending on your definition if the word ‘sexy’). We get it, Jen, your body is incredible for someone nearing her 50’s, but maybe this is a little overboard?

The holes and cut-out panels are so numerous in this Julien MacDonald dress that we’re assuming she was just sewn into this thing or else it was spray-painted on to her body with a 3-D printing gun. It’s a mystery to us. But the biggest mystery of all is how she looks this amazing at 47 years old in something this ridiculous. #Notfair.

17 Wardrobe Malfunction On Stage

During her Dance Again World Tour, one rather raunchy performance in Italy caused J-Lo to have an embarrassing slip mid-routine. Oops! It doesn’t help that she was wearing this impossible bodysuit and bra combo at the time. While dancing energetically to one of her hits in Bologna’s Unipol arena, J-Lo’s chest almost escaped from her criss-cross bralette. But like a pro, she carried on with the routine.

One of her back up dancers took the opportunity to cover Jen up again, and by the sound of things, there might be a regular job in it for him. Apparently, she suffered the same fate with a bodysuit during the London leg of her tour as well. Sounds like the bodysuit could be cursed? Or just maybe, Ms. Lopez’s stylist needs to invest in some better quality body tape.

16 That Versace Dress At The 2000 Grammys

via:Daily Mail

We couldn’t make this list without mentioning the crème de la crème of all outrageous J-Lo dresses. Arguably her most well-known red carpet look to date (and one of her most bizarre fashion faux-pas) was this iconic Versace dress she wore to the 2000 Grammy Awards. We’re of course playing fast and loose with the word ‘dress’ here. 18 years later and this still resembles a maxi kimono at best.

Lopez must have had some industrial strength tape in place that night or nerves of steel (probably both). The look baffles us as much now as it did back in the day. Sure, she might seem covered up compared to the red carpet stylings of Kim K or Rihanna that we’re used to, but J-Lo broke fashion boundaries with this incredibly brave Versace gown and the rest is history.

15 Skintight LBD On The ‘Tonight Show’

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One of Jennifer’s hottest looks in recent years is when she appeared on The Tonight Show in 2014. The stunning singer and American Idol judge looked absolutely stunning–if a little uncomfortable–when she joined host Jay Leno for a chat in this super tight leather and lace bodycon dress. We all have that one staple little black dress at the back of our wardrobe, but none are quite as interesting as this.

J-Lo’s Ermano Scervino dress was a sexy mix of leather and lace and hugged on to her incredible curves, whilst revealing a cheeky hint of her cleavage and torso. Host Jay Leno even complimented her on the fact that she hadn’t seemed to have aged a day since her last appearance on the show... some 17 years before. It’s true, this woman does not seem to age.

14 Taking The Plunge

No stranger to a plunging neckline (see her iconic 2000 Grammy Awards dress), J-Lo went for a bold look in more ways than one in this hot vampy dress she wore to the 2012 Oscar after-party. The ultra-glam Vanity Fair party traditionally held after the Oscar ceremony always serves up a who’s who of the fashion and film world, and Lopez made sure she was noticed.

The 2012 red carpet boasted many gorgeous gowns but the standout dress belonged to our very own Jenny from the block, thanks to this knockout maroon red plunge dress. This is typical J-Lo style when it worked best—racy yet classy. Thank legendary dress designer for the stars, Zuhair Murad, for this gorgeous sequinned creation.

13 Sheer Plum Dress At The HRC Dinner

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J-Lo looked jaw-droppingly stunning at the 2013 national HRC Dinner back in 2013. This gorgeous semi-sheer plum dress is a prime example of how Ms. Lopez can flaunt so much of her amazing figure whilst keeping relatively covered up. Jen turned to one of her favorite red carpet designers, Zuhair Murad, for the esteemed event in Washington, which is really close to her heart.

This Human Rights Campaign Dinner in particular was honoring Lopez with an ‘Ally For Equality’ award for all her support and work for the LGBT community over the years. J-Lo looked suitably demure yet sexy when she rocked up in this burgundy velvet number with sheer side panels. We’re getting vibes of some kind of sassy Disney villain here. Mature and elegant, yet vampy and diva-like.

12 Beyonce’s Style Inspiration?

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Beyonce and J-Lo have quite a lot in common. As well as both being feisty performers and empowering role models, the two veteran pop divas also appear to have the same taste in fashion a lot of the time—specifically a love for full-length nude gowns. A lot of people think Queen Bee kicked off the trend when she stepped out in that show-stopping Givenchy dress at the 2015 Met Gala, but J-Lo kind of got there first.

Bey may have made the sheer trend famous since she also wore that lace Michael Costello dress a year before at the 2014 Grammys, but as we can see, Lopez stunned the awards season a year earlier when she wore this romantic yet sexy lace gown for the 2013 Golden Globes. Who wore the dress better? Tough call.

11 Barely There In Vanity Fair Gown

via:Daily Mirror

Like so many of J-Lo’s outfits both on and off stage, this is that kind of outfit where it’s hard to tell where the bare leotard begins and where her skin ends. When she’s not performing in one–and almost suffering a slight wardrobe slip-up in the process–Lopez likes to bring out some of her favorite sheer bodysuits to some of Hollywood’s most glam after-parties.

She went with this mesmerizing dress and leotard combo for the Vanity Fair after-party at the 2015 Oscars, and the sheer material is so close to J-lo’s actual skin tone that it’s almost magic. The pretty rhinestones and embellishments appear to be floating near her skin as if she were really only wearing cleverly-disguised body paint instead of a genuine bodice. We wouldn’t put it past Jen to try this out for her next red carpet dare.

10 All Wrapped Up In A Bow

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What does J-Lo wear when she’s bored of wearing skin-colored bodysuits on stage? She tries out the ones that look like a gigantic bow, of course! While performing on a show in Dubai late last year, J-Lo made quite the statement when she took to the stage in this blue velvet bodysuit. Wow! The term ‘suit’ might be a little loose in this context, though (it’s a good thing the knot in the middle of her waist wasn’t).

For the fans sitting further back in the arena, we can see how J-Lo’s bow leotard (designed by celeb bodysuit extraordinaire and stylist to Lady Gaga, Bao Tranchi) might look kind of impressive, even artsy. But up close, it looks like a PR nightmare waiting to happen. Still, you have to admire J-Lo’s gutsy outfit choices at 48 years old.

9 Starry Blue Jumpsuit


This might be one of Jen’s more covered-up looks in recent years, but when she covers more flesh than usual, she tends to compensate by going with see-through material for her dress as well as making sure she has some major cleavage on show. This was another one of her outfit switcheroos at the American Music Awards in 2015, and she took a breather in-between dresses for a jumpsuit instead.

Jen’s near-transparent romper featured stars and a glitzy sparkle design which she teamed with a matching belt. (To be fair, though, nobody will have been staring that far north of her outfit!) It might have been an unusual piece of anyone else but J-Lo wears it pretty well, even if her curvaceous busty figure looks as if she’s about to burst through at any minute.

8 Barely Keeping It Together

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This angelic yet sexy wrap-around dress was so in danger of staying together that it had to be held in place by what looks like an oversized safety pin! You know Lopez is a stone cold stunner when she can make a novelty-sized safety pin work with an outfit. (Seriously, how does she even do that?) J-Lo wore this fashion faux-pas miracle at the Singapore F1 Grand Prix in 2004, seemingly to match racy cars with an even racier outfit.

Jen sported this hot cut-out number while performing her explosive set shortly before the Grand Prix took place. If it looks a little more covered up for J-Lo’s tastes, it didn’t last long as she soon lost the flowy dress part of her outfit and stripped down to a revealing white leotard, and gyrated around the stage like nobody’s business.

7 Cheeky Met Gala Gown

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The annual Met Gala in New York is the definitive place to be seen in a show-stopping dress. Beyonce stunned photographers with her nude figure-hugging gown a few years back, and we’ve lost count of how many years Kim K has walked down those red steps with an eye-popping outfit on. As evidenced by this photo, the 2015 Met Gala was J-Lo’s time to shine, and she certainly did that.

The then-45-year-old Jen looked absolutely stunning in a ruby Versace gown that exposed so much of her bare hips and backside that you could pretty much count the birthmarks. Her dress was covered in fiery red sequins in the shape of a dragon, but it barely covered her chest and bum. There aren’t many women who can look classy while half-bare on the red carpet, but J-Lo’s definitely one of them.

6 Donna Karan ‘Cape’ Gown

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Compared to a lot of her other dress choices on this list, J-lo’s curvy figure isn’t quite on full display here (but the way this outfit is put together suggests that could all change if someone stood on her train). For the 2014 Billboard Awards, J-Lo paired a cute Ariana Grande-style hairdo with this fiery red cape dress by Donna Karan, and in our opinion, she looks too amazing for a woman in her mid-40’s.

She certainly has the pins and body to carry off this kind of hot superhero look, but the high slits are kind of making us nervous (or rather, we’re imagining what would inevitably happen if we tried wearing something like this). If it weren’t for the belt essentially tying together the red panels of chiffon, this would be wardrobe malfunction city.

5 The Britney-esque Bodysuit

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Britney Spears was the first to rock the embellished skin-color bodysuit (both on stage and famously in her video for ‘Toxic’), but no hate on J-Lo for trying this one out too as she looks stunning and it’s a look that obviously works just as well for her. The problem with wearing these kinds of bodysuits on stage is that a raunchy performance is often in danger of showing the crowd your real “bareness.”

This almost happened to Lopez one night during a performance in Miami back in 2015. She was wearing a similar skin-color and bejewelled bodysuit and was dancing a little too ferociously when her zipper came undone at the back. Ever the pro, J-Lo kept on dancing. But had her set gone on any longer, this could’ve made Janet Jackson’s famous slip-up look modest!

4 Covering Her Globes In Gold

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Three guesses where J-Lo was when she sported this appropriate dress? Jen debuted this precarious-looking gown at the 2009 Golden Globes, and it’s not the most flattering (nor supportive) thing she’s ever worn. The flimsy halterneck of gold material kind of looks as if it’s hanging down freely without the aid of any kind of modesty tape. But even with some, this kind of looked like a malfunction waiting to happen.

There’s no denying that J-Lo doesn’t look stunning as always and it does a great job of flaunting her glorious curves, but the longer you look at this thing, it kind of resembles more of a skirt and matching scarf than it does an awards gown. Maybe this wasn’t difficult to put on, but Jen probably struggled to keep it on for the rest of the night!

3 What Is Actually Going On Here?

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Anyone can see that Jen from the block has a body to die for and one of the most enviable booties in the business, but that doesn’t necessarily mean everything looks good on her. Does it? As part of her many wardrobe changes during the 2015 American Music Awards, J-Lo donned this incredibly bizarre dress that technically shouldn’t even be called a dress.

And how did she even get in this thing? It looks like she was attacked by neon Spiderman. In a bid to show off literally every inch of flesh she has, Jen changed into this powder blue monstrosity that seems to resemble dyed sailing rope and curtain cords than actual clothing. Perhaps it does have one thing going for it though—this would’ve made one heck of an artsy tan line.

2 Figure-Hugging Mermaid Gown

via:Daily Mail

The 2015 American Music Awards was not only a big night for J-Lo’s music career, but it was also a chance for her to debut some of the most risque fashion statements we’ve seen her in to date. Throughout the course of the awards show, Lopez made an epic total of 11 costume changes in-between performing and presenting the songs, and one of them happened to be this look. The Little Mermaid who also wore very little.

As you can see, the silver beading embellishment barely conceals the outline of her lady bits and the sheer dress–while flaunting her fabulous hourglass figure–is more trying-hard than sexy. We’re trying to figure out how she actually got into this dress in the first place without tearing the sheer part in half.

1 Barely There In Silver Couture

Ms. Lopez certainly seems to have a fondness for full-length gowns that leave nothing to the imagination, and this eye-catching number at the 2015 Billboard Music Awards is no exception. Here, J-Lo wears a very sheer and silvery Charbel Zoe Couture gown, and no diss to her designers, but they missed a spot up top. Quite a big spot to be exact!

For somebody who loves to wear dresses with intricate jewels and embellishments, Jenny from the block doesn’t seem to care about their real purpose—a way to cover your modesty. The art of a sexy dress should surely be one that puts all the embellishments in the right places. Let’s get real, though. When you look as good as this woman does, why not flaunt it?

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