Most memorable fashion from the 1998 Golden Globes

By Bryanne Salazar 10:13am PST, Dec 13, 2017

On Jan. 7, 2018, the Golden Globe Awards are back for a 75th year. The ceremony, which honors the best of both TV and film, is also our chance to ogle celebrities in their designer duds as they walk down the red carpet. In celebration of the annual award show, Wonderwall.com is taking a look back at some of the most memorable fashions from the 55th Golden Globe Awards two decades ago in 1998… starting with this number. Jennifer Lopez has never shied away from making a statement on the red carpet and that was true in 1998 too. At the 55th Annual Golden Globes, J.Lo rocked a colorblocked body-con dress that showed off her flawless figure. Fresh off the fame of her breakthrough performance in "Selena," Jennifer was ready to step out in style and turn a few heads in the process. Keep reading for more…

As you look at this adorable picture of Leonardo DiCaprio and Kate Winslet at the 1998 Golden Globes, know that "Titanic" was still in theaters and the two were suddenly more famous than ever before. Leo arrived in a traditional black tux with a bow tie (and looked not a day older than 12, let's be honest) while Kate racked all the fashion musts for the '90s including a stretchy nude lace gown (courtesy of designer Pamela Dennis), a choker, a super-dark lip and a messy updo that Gwen Stefani circa No Doubt 1997 would be proud of. While the style is way not okay today, it was pretty cute back then.

Even though this is a Giorgio Armani gown, we can't help but think Angelina Jolie (who won for best supporting actress in a miniseries that night) should have worn something else, like, anything else. Her amazing figure was hiding beneath swaths of sheer curtains (okay, it was a shawl) and the glittery sequins, while nice, adorned a dress that didn't quite fit her frame. The awkward mid-calf cut and thigh-high front slit made this dress look like a maternity gown that was trying to be sexy.

Flush with shimmery satin, a flowing train and a cut that hugged every curve, Minnie Driver looked hawt in this Givenchy mermaid gown at the 1998 Golden Globe Awards.

It's like we took a trip in the way-back-when machine to a time Alec Baldwin and Kim Basinger were still married. At the 1998 Golden Globes, Alec went with a traditional black tuxedo while Kim opted for a black satin number with a fitted bodice, poofy skirt and… is that really a black cardigan? Yikes. The look wasn't bad, it was just so basic and the matching pointy-toe black heels just added to the "We're going to a funeral" charm.

Former lovebirds Tate Donovan and Jennifer Aniston hit up the 1998 Golden Globe Awards in some of the most okay-est fashion of the night. Did either look bad? No. Did Tate or Jennifer look like they put a lot of effort or thought into their looks? Definite no. Tate's basic tuxedo and Jen's even more basic slate grey sheath gave the couple a "we forgot about the ceremony until the last minute" kind of style. Like we said, it's the okay-est of the night.

Sandra Bullock killed it at the 1998 Golden Globes in this heavily embroidered black Dior gown with sheer shoulders, jeweled-chain embellishments and a soft, elegant updo. While the dress was totally 1990s, the detail and drama made her pop on the red carpet (in a sea of solid colors) while adding a softer, feminine touch to her look.

Julia Roberts, who arrived at the 1998 Golden Globes with her "My Best Friend's Wedding" co-star Rupert Everett, also donned an embroidered gown, but hers was even more interesting than Sandra Bullock's. Julia's halter-style Todd Oldham column dress with bright, bold embroidery covering every inch made her stand out in the best way possible. While we think she could have had more fun with her shoes (plain black with that dress just won't do, honey) we think this was a major yes moment on the red carpet. Rupert didn't look so bad himself with his Miami-cool open neckline and loose-fitting suit that whispered, "I didn't try hard but still look fine."

This picture of Winona Ryder and Gwyneth Paltrow at the 1998 Golden Globes reminds us all that they used to be friends! But what the heck were they wearing? The actresses were in their mid-20s at the time and both were established in Hollywood, which means they knew better than to throw on what amounts to a slip (Gwynnie) and the same outfit one would wear to an interview for an office job (Winona). At least they've learned how to dress better for award shows nowadays!

We couldn't track down the designer of this gorgeous, shimmery taupe gown but we can comment on how Jada Pinkett Smith (who had just tied the knot with hubby Will Smith a few weeks prior) was clearly feeling herself in this dress. It wasn't just the gown that was making her glow either. Look closely at her tummy and you'll see a barely perceptible baby bump. Jada was a little more than three months pregnant with her first child, son Jaden Smith, at the time this photo was taken. With her hand placed on her belly, we're sure she knew and was basking in the joyful news.

We love Julianne Moore (we really do) but we just don't know how it's possible that 20 years ago she looked 20 years older than she does today. The frumpy navy blue Richard Tyler gown wore her to the awards show, not the other way around. We're going to cut the famous redhead some slack though, because she'd just given birth to her first child a little over a month earlier and still looked better than any of us on our best day.

We have no idea who the beauty on Djimon Hounsou's arm was at the 55th Annual Golden Globes but together, they were a vision of perfection. At the time of this photo, Djimon was one of the biggest breakthrough stars of the year thanks to his incredible performance in the historical drama "Amistad" (which had been released just three weeks earlier). The combo of their super-sexy style (her ruched green-gold dress and his sleek black tuxedo were everything) and gigantic smiles made them one of the best dressed couples on the red carpet.

When talking about fashion from two decades ago, it's important to remember that hemlines and style trends were different (at least that's what we're telling ourselves about Brooke Shields' 1998 Golden Globes dress). While the color looked stunning on the former "Suddenly Susan" star, the boxy lower half of the dress didn't accentuate her killer figure. Plus the elongated matching wrap only served as camouflage, hiding her toned arms and enviable waistline. What she got right was the bold red lip, loose hair and the fact that she was Brooke Shields (meaning she could wear whatever she wanted and still look fierce).

Just 10 days before the 1998 Golden Globes, most of America didn't know the names Matt Damon or Ben Affleck. All that changed with the Jan. 9 release of "Good Will Hunting" — the film the duo wrote and starred in that launched their careers. The boys, riding high on their success, showed up the Globes looking dashing and dapper in matching black tuxedos. Ben opted for a long tie while Matt sported a more traditional bow tie. Our only complaint? Ben's pants were MC Hammer big and could've been taken in a few dozen inches.

Quirky British actress Helena Bonham Carter is as authentic and original as they come when it comes to fashion, so we weren't surprised by her 1998 Golden Globes look. The loose-fitting, sheer-sleeved, matronly black gown was actually pretty tame in comparison to some of Helena's other red carpet looks over the years. We loved her spiky short hair that subtly told onlookers "I don't give a f— what you think."

In January 1998, Ellen DeGeneres had only been out as a gay women for around nine months and her romance with actress Anne Heche was one of the most talked-about relationships in Hollywood. When the lovebirds arrived at the 55th Annual Golden Globes in color-coordinated outfits, the world let out a collective sigh because, how cute could they be? In retrospect, Anne's bulky crushed velvet, layered look and awkward evening shades were in stark contrast to Ellen's elegantly tailored suit. Sure, the colors were complementary, but Anne looked like she wasn't even sure where they were that night.

In this outfit, Alfre Woodard proves that no matter the decade, she's a stunner. The former "Miss Evers' Boys" star (who won the Golden Globe that night for best performance in a TV movie) arrived on the red carpet in a floor-length beaded gown with metallic embroidery that sparkled as she moved. The dress was sexy in 1998 and would still be sexy in 2018.

We're giving mad props to movie star Jack Nicholson's 1998 Golden Globes attire. The acting legend (whose movie "As Good as it Gets" was still in theaters) was as suave as they come in a tailored blue tuxedo he accessorized with jet black shades and a hefty cigar. Classy, Jack, really classy.

Although actress Lara Flynn Boyle and Jack Nicholson weren't yet a couple at the 1998 Golden Globes, we can't help but wonder if her shimmery white satin bias-cut gown and frothy feather boa might have caught his eye? The actress went for full Old Hollywood drama on the red carpet, and we think it worked.

What we love about Jenna Elfman's 1998 Golden Globes gown is that it refused to conform to the fashion standard of the era. The late '90s were all about dark colors and grunge. Jenna's gown was the complete opposite. The chartreuse green V-neck gown featured sheer black lace trim at the bottom as a sort of early homage to hombre. While we're not crazy about the color combo or how it overpowered Jenna's fair complexion, we do respect her red carpet bravado.

We're in love with Gillian Anderson's edgy black gown with a scalloped neckline and corset waist. Pairing the dramatic look with a bold red lip (to complement her gorgeous red hair) was a genius choice as Gillian looked like a vintage Hollywood starlet with a touch of '90s angst.

Shame on Prada for allowing Sigourney Weaver to arrive at the 1998 Golden Globes in nothing more than a slate gray slip with a pink net on top. The awkward hoop around her calves made the actress look like her body was caged in the oddly short (and wrinkled!) dress. We're also not sure what she was going for with the black shades, but they didn't help pull the look together. On a brighter note, we think she killed it with her pink shoe game.

At the 1998 Golden Globes, Madonna channeled her inner emo goth vixen with this jet black Balenciaga gown and we're as confused as you are about the look. Her messy, flowing hair and long-sleeved, low-bodice dress were uncharacteristically demure and at the same time shocking. Could Madge really not find a comb or a dress that didn't make her look like the bride of Count Dracula?

Awkward pose aside, we think "Just Shoot Me" star Laura San Giacomo's 1998 Golden Globes little black dress was an excellent fashion statement. Featuring playful fringe, glistening beadwork and a sassy side train, the look was less "cocktail hour" and more "red carpet ready." Plus, we loved her choice to keep the jewelry simple.

We're not going to hold this 1998 Golden Globes look against "ER" actress Gloria Reuben for the sheer reason that her fashion game has improved by leaps and bounds since this unfortunate dress. The deep-V neckline could have worked (as it showed off her amazingly toned arms) but as the dress faded into a deep blue, it caused her lithe frame to look blocky and square-ish, making her waistline all but disappear while exaggerating her shoulders.