These Were the Best Celebrity Outfits From December 1998
Fun fact: Some of the most stylish celebrities two decades ago are still some of the most stylish celebrities today. Take, for example, Jennifer Lopez, whose wardrobe is still breathlessly covered as often as it was in the '90s. Just for fun—and because '90s nostalgia is kind of the best nostalgia—we took a trip back to December 1998 in search of the best celebrity winter outfits of the '90s. The likes of Gwyneth Paltrow, Julia Roberts, Jessica Biel, and more were quite busy with movie premieres, travel, and holiday-season events that month, so our search proved quite fruitful.
Two decades ago, as is the case in December 2018, the celebrity set flaunted many "extra" looks and, unlike in 2018, lots of all-black outfits. With plenty of holiday parties and gatherings with family and friends on the horizon, you're sure to gather some inspo from the following 20 standout celebrity outfits from December 2018. Keep scrolling to see what we mean. FYI: They're mostly in random order, but we saved the best for last.
I dress worth showing off, indeed, Salma.
We're re-creating this exact outfit combo for our next holiday party.
Dave Benett/Getty Images
Jessica Biel pulled off the '90s grunge look with aplomb.
Twenty years later, Jennifer Lopez is still knocking it out of the park at every event.
This minimalist look will never go out of style.
We're pretty sure Madonna could and would still rock this today.
We want to wear this jeans-and–ankle boots combo stat.
Julia Roberts's off-duty style may be simple, but then she steps onto the red carpet in looks like this.
Leather coats are back, and this may be exactly why.
That purple coat, though.
So, Angelina Jolie's style clearly hasn't changed much.
Proof of the power of a good statement coat.
Note the headband, which is a '90s trend that's back in a big way.
The sweater styling, leopard-print bag, and patent leather shoes are all very 2018.
Turquoise jewelry is another accessory trend that's making a comeback.
Nineties outerwear inspo.
We just had to include this over-the-top look.
The bag, the shoes, the furry straps… It's all just too good, and we'd wear it tomorrow.
Next up, what cool girls were wearing in fall 1998.
Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
This Sweater Will Never Go Out of Style—Here's How French Women Are Wearing It Now
Effortless and chic? Oui!
By Jennifer Camp Forbes
-
I Know You're Stylish If You Tuck Your Jeans Into Boots Like These 5 Chic Women
Don't be scared.
By Nikki Chwatt
-
New Yorkers Will Wear This Celeb-Concocted Ankle-Boot Outfit for the Next 3 Months
Sydney Sweeney just modeled it for us.
By Allyson Payer
-
If You're Anti–Skinny Pants, This Is the Outfit That'll Make Baggy Trousers Look Current in 2025
Hailey Bieber knows the way.
By Allyson Payer
-
The Elegant Outfit Hailey and Zoë Pack for Every Destination, From London to NYC
No matter what.
By Eliza Huber
-
This Cheap Shoe-Styling Trick Is How to Keep Cropped Jeans From Looking Dated in 2025
Putting this one in my back pocket.
By Allyson Payer
-
This Is How to Wear Chunky Sneakers in Paris Without Looking Like a Tourist
Aka, how to blend in with the French citizens.
By Allyson Payer
-
I'm Sorry, or You're Welcome—2025 Marks the Skinny-Pant Era, so Here Are 8 Looks to Try
So chic they just might change your mind.
By Anna LaPlaca