STYLE EVOLUTION

Jennifer Lopez’s Boy Toys, from Diddy to Drake, Have Never Been Able to Measure Up to Her Style

The 2000 MTV Video Music Awards
WireImage/Getty Images

Jennifer Lopez‘s daring, curve-baring dresses on the red carpet since she stepped into the spotlight in the ’90s haven’t just proved JLo likes to keep it glitzy; they’ve also put the various boy toys that have appeared alongside her throughout the decades to shame. That started out all the way back with her first love, David Cruz, whom she dated for 10 years in a variety of ’80s and ’90s fashions before moving on to the likes of Wesley Snipes, Diddy, Ben Affleck, and Marc Anthony—and outfits that have involved fur jackets, bandanas, sequins, and crop tops, the latter of which were most memorably showcased alongside Affleck in the video for “Jenny from the Block.” Three husbands, two twins, and a handful of much younger beaus—from her backup dancer Casper Smart to Drake—later, JLo still hasn’t found her style parallel, though she’s definitely still pulling out all the stops for new flings like A-Rod. From the iconic Versace dress she wore to the Grammy Awards with Diddy in 2000 to the bling that made it through her blurry Instagrams late last year with Drake, take a look back at JLo’s style throughout the years—plus all the men she’s made pale in comparison—here.

1
Jennifer Lopez and David Cruz (1984-1994):

JLo may have started seeing David Cruz when she was just 15, but she went on to date her first love for a full decade, making for plenty of ’90s fashion moments even after they split up, like this tank dress in 1995.

2
Jennifer Lopez and Wesley Snipes (1994-1995):

Even though JLo met the actor Wesley Snipes when filming a sex scene she later publicly called “horrible,” she went on to date Snipes briefly after filming wrapped, this time keeping showcasing a bit more demure ’90s fashion.

3
Jennifer Lopez and Ojani Noa (1997-1998):

Long before JLo’s first husband Ojani Noa threatened to release a sex tape of her last year, the pair met in a Cuban restaurant where he was a waiter, making for a year-long marriage that saw JLo in body con dresses and blue eye shadow while he opted for hot pink button-ups.

4
Jennifer Lopez and Tommy Mottola (1998):

Fresh from divorcing Noa, JLo broke out the thigh-skimming dresses and started straightening her hair for her fling with music executive Tommy Mottola—also a recent divorcé, who was rebounding from Mariah Carey.

5
Jennifer Lopez and Diddy (1999-2001):

In their two years of dating, JLo and Diddy hardly shied from the opportunity to coordinate outfits, matching in white (but sadly not in crop tops) for events like the 2000 VMAs.

6

Diddy reprised the all-white look at the Grammy Awards later that year, while JLo busted out a green Versace dress now so iconic, it has its own Wikipedia page.

7
Jennifer Lopez and Cris Judd (2001-2003):

Cris Judd was the first of several back-up dancers JLo ended up having flings with, and definitely the first she married, marking a two-year relationship full of early aughts style and hairdos like a mop of floppy curls.

8
Jennifer Lopez and Ben Affleck (2002-2004):

Bennifer met on-set of Gigli in 2002 and dated for the next two years, until calling off their engagement in 2004—a time full of plenty of t-shirts and off-color ties for Affleck, and fur and floor-length, high slitted gowns for JLo. (Not to mention all her crop tops alongside Affleck in the video for “Jenny from the Block.”

9
Jennifer Lopez and Marc Anthony (2004-2011):

Post-Ben, JLo found her groove with Marc Anthony, whom she was married to for seven years, having twins named Max and Emme before divorcing in 2011, a year that nonetheless saw JLo looking her best in silver Emilio Pucci sequins at the Grammy Awards.

10
Jennifer Lopez and Rodrigo Santoro (2011):

That same year, JLo was rumored to have had a fling with another mustachioed man: her What to Expect When You’re Expecting costar Rodrigo Santoro, whom she made plenty of red carpet appearances with, like in this sheer gown at the film’s L.A. premiere.

11
Jennifer Lopez and Bradley Cooper (2011):

Other than a few sneaky dinners, JLo and Bradley Cooper were rarely seen in public together, but they made enough appearances together—even front row at Tommy Hilfiger—for JLo to bring out the thigh-high boots.

12
Jennifer Lopez and Casper Smart (2011-2016):

JLo’s real beau post-Marc Anthony, though, was another, much younger backup dancer named Casper Smart, whom she dated all the way up until 2016, when she wore this much more sophisticated take on her Diddy-era head-to-toe white.

13
Jennifer Lopez and Maksim Chmerkovskiy (2014):

Though things were never confirmed between the pair, it’s hard to imagine there wasn’t tension (or at least plenty of sweat) between JLo and the Dancing with the Stars star Maksim Chmerkovskiy. (As her first husband Ojani Noa can attest, JLo does seem to love a hot pink button-up.)

14
Jennifer Lopez and Drake (2016):

It seemed entirely possible that JLo and Drake’s much buzzed about relationship had continued into 2017 until this week, when the first song on Drake’s new album made it pretty clear things have ended with the lyrics “I drunk text J. Lo / Old numbers so I bounce back.” Still, the Instagrams of their short-lived time together live on, blurry as they are, but clear enough to show the pair at least shared a love for bling.

15
Jennifer Lopez and Alex Rodriguez (2017):

Things appear to still be starting out for JLo and Alex Rodriguez, which seems to be why the pair left dinner separately in Miami—and why JLo pulled out an eye-catching, tight-fitting dress in what now seems to signal a serious move for her: all-white.