Top 10 Best Jennifer Lopez Fashion Moments

#10: Baby Pink Velour One-Piece Tracksuit Total Request Live (2002)

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Everything about this outfit is so 2002, in the most amazing way. From the oversized hoop earrings and the color coordinated cap, to the stiletto and sweats combo, this ensemble just screams early aughts. J Lo was perfectly on trend in this baby pink lounge suit that helped set the standard for cool girl outfits for years to come. In retrospect, it’s hard to explain the one leg slightly rolled up look, but if you were a teenager in 2002, you’ll remember that this was totally a thing.

Many of Jennifer Lopez’s most iconic looks are on this list because they left a lasting impression by pushing boundaries, but this one is memorable because of how timelessly elegant it was. When Lopez attended the Golden Globe Awards in 2011, she wore a white Zuhair Murad dress that made her look like she was walking on air. She paired the gown with a sparkling capelet that takes the whole outfit over the top. And never one to be too understated, she paired the outfit with oversized earrings for a little extra bling.

At the height of the Bennifer era, Jennifer Lopez attended the Oscars on the arm of Ben Affleck but totally stole the show in this Valentino gown. The one shoulder design looked timeless and yet still of the moment in 2003. Jennifer sure knows how to pick outfits that are flattering to her; the pale green shade of this dress perfectly complements her bronzed skin. She looks simply statuesque, even when standing beside Oscar himself! This is one of her more demure looks, which just goes to show that this multi-talented performer can shine in just about any style.

When Jennifer attended the Academy Awards in 2015, she managed to pull off not one but two incredible dresses. For the ceremony itself, she wore a stunning nude/blush colored ball gown by Elie Saab Couture. When the big event was done however, she put on an equally show stopping dress for the Vanity Fair after party. She went a little sultrier with this Zuhair Murad Couture number that unabashedly showed off all of Lopez’s best assets. The white fur stole added an extra fashionable touch to the overall look.

Undeniably one of the most risque dresses Jennifer has ever worn to a major awards show was this Chanel gown that she chose for the Oscars in 2001. While the skirt was full and even described as “frumpy” by at least one critic, the asymmetrical top was very sheer, shocking many in a pre-”free the nipple” time period. Whether you loved it or hated it, it was undoubtedly one of the most talked about looks of the night. Today? We doubt anyone would have even batted an eyelash.

Not everyone can pull off a bright yellow gown on the red carpet, but if anyone can do it, it’s Jennifer Lopez. Not only did this Giambattista Valli gown have a striking color, but it also had an unusual silhouette. The top was fitted with draping that flattered her figure, and the skirt had a sky-high slit that let Lopez show off her incredible legs. On top of that, she went all out with the sparkle in her accessory choices. Even in her 40s, Lopez does not shy away from making bold fashion choices, and they keep working.

Jennifer Lopez has been called a golden goddess on more than one occasion, but she perhaps never more accurately embodied that descriptor than at the 2009 Golden Globes. The intricately draped gown by Marchesa was called one of the best Golden Globes dresses of all time by Glamour Magazine and we tend to agree. It was undoubtedly a daring choice, and we can’t even imagine how she avoided a wardrobe malfunction all evening considering how precarious the fabric seemed in terms of its placement. She certainly isn’t afraid of making a statement!

Jenn surely knows how to work her curves, and this dress from the 2002 Oscars might just be the best example of her pulling it off flawlessly. She chose a pink Versace gown fit for a princess that had a sculptural design that felt distinctly modern. Despite the wow-factor of her dress, she opted to go big with her hair as well, with voluminous curls giving an extra “va va voom” to the finished look. Whether she’s aiming for sexy or elegant or something in between, Lopez always manages to pull it off.

Certain award shows tend to call for more outside the box outfits, and the VMAs are definitely one of them. You won’t be seeing your typical elegant ball gowns here! In 2000, for her 3rd VMAs, J Lo was already one of the most anticipated arrivals on the red carpet. She came with her boyfriend at the time Puff Daddy, and wore a Sean John crop top to show her dedication to him. From our modern perspective, the belly baring all white outfit may seem a little bit shocking, but hey, this was the height of style at the turn of the millennium! Is the red carpet bandana back yet? Before we unveil our top pick, here are a few honorable mentions. Vintage Green Gown by Rita Watnick at Lily et Cie 78th Academy Awards (2006) Bright Orange Grecian Style Dress by Michael Kors 61st Golden Globe Awards (2004) Light Blue Sheer Cape Gown by Valentino Met Gala (2017)

… Could our number one pick have possibly been anything else? There is no more iconic look in Jennifer Lopez’s repertoire than this head turning number that she wore to the Grammys in 2000. She made headlines with the ultra deep plunging neckline that went below her bellybutton. It’s difficult to imagine anyone else pulling off a dress like this one, or honestly even putting it on in the first place! In fact, this Versace gown was so buzzed about that it is credited with being one of the reasons that Google Images was created!