1999 fashion trends of 3 different styles of women's outfits

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Let’s party like it’s 1999! Come on in.

People are freaking out about the “Y2K bug” and stockpiling survival supplies. Celine Dion is wearing a backward white suit at the Oscars and Bill Clinton is getting the chop. What a year. 

In terms of TV and movies, 1999 was colossal. We had ‘Freaks and Geeks’, ‘The Sopranos’, and ‘Family Guy’ bursting into our homes. At the cinema, some of the best-rated films of all time were being released, such as ‘The Matrix’, ‘Fight Club’, and ‘American Beauty’.

1999 though was ultimately the year of the romcom. Think about it, we had:

  • ‘Notting Hill’
  • ’10 Things I hate About You’
  • ‘Runaway Bride’
  • ‘Never Been Kissed’
  • ‘She’s All That’

How many of those do you still watch on a lazy Sunday when no-one’s watching? I thought so. 

Celebrity fashion in 1999 had some unforgettable hits. Notably:

  • Shania Twain’s full white dress at Grammys
  • Gwyneth Paltrow and Cate Blanchett’s Oscar dresses
  • Keri Russell and Debra Messing’s White Bandeau column dresses at the Emmy

The Emmys also saw one of Jennifer Aniston’s most loved looks. Her dress featured a chocolate-brown sheath skirt with a gold and red embellished sheer top with a high neckline. Her hair was twisted and twirled into beachy, messy glory, solidifying her as the bronzed, California cool-girl of the decade and beyond. 

Here are some of our favorite fashion moments and trends of the last year of our favorite decade! 

Madonna at the Grammys: a white tank and embellished trousers

One thing I love about the 90s was that the red carpets were just as fashion-forward (if not more) than today, but they didn’t take themselves so seriously. Hair was often simple, silhouettes were relaxed, and makeup was fresh. Of course, there were the ultra-styled looks, but simplicity and laid-back glamour were celebrated. 

For example, at the 1999 Grammy awards, Madonna wore a white tank top and embellished purple trousers. Her dark hair had a simple middle parting, and her bra straps were exposed. With her sparkly, beaded pants she wore white satin stilettos, and her lips were classic red. 

Try it: 

  • Search for a pair of loose-fit trousers that sit low on the hip, in a shade such as lilac or magenta. Try your hand at embellishing the pockets, hemlines, or all over with crystals and beads. Pair with a simple tank or tee, slick on a bold lip and skip to the party 
  • If the embellished trouser look is a little too far, swap it out for an embellished midi skirt but keep the white tank and pumps 

Lauren Hill’s top and skirt at the Grammys, and Halle Berry’s set at the Emmys 

Lauren Hill’s Grammy look stood out to me for several reasons. For one, her mauvey-pink makeup was so stunning it’s hard to fathom that a face can be that beautiful. And second, her flared satin skirt with tulle overlay reminded me of the outfits my sister and friends wore to the school dance in the late 90s, early 00s (I wore a 50s wiggle dress, oddly). 

The flared tulle skirt with cropped top or tank was a 90s evening wear staple. Halle Berry wore this look at the 1999 Emmy awards, with a black tulle skirt and brown, embellished tank. The style was girly and playful yet cool and deconstructed like a princess who was sick of her gown so she cut it in two. 

Try it: 

  • Not all of us are comfortable showing our midriff, and that’s a-okay because we can adjust the outfit’s proportions to fit our comfort zones. Pick a high-waisted skirt and a very slightly cropped top so only a teeny slither of the waist is exposed. Or, pick a bodysuit to go with your flared skirt for extra coverage
  • For daily wear, look for a bell-shaped midi skirt as opposed to a full maxi. Skirts that hit below the knee or where the calf tapers are super-flattering and versatile. They don’t drag in the dirt and they show off your shoes 
  • Pick a flared, bell-shaped tulle skirt and wear with a worn-in graphic tee or even a marle grey ribbed tank 

Casual But Cool: Tanks Tops from the 90s Can Still Be Worn Today

Clean white minimalism at Calvin Klein Spring Ready-to-Wear 1999

Calvin Klein is known for clean, minimal, sleek looks, worn by waif-like models and celebrities with willowy limbs. Kate Moss was the ultimate Calvin Klein model, wearing silver and white slip gowns like they were part of her body. 

 

Gwyneth Paltrow wore a white beaded Calvin Klein slip gown at the 1996 Oscars, a true representation of the CK 90s style. His 1999 Spring ready-to-wear collection featured simple white long-sleeved tops with satin pencil skirts, simple grey suits, and bandeau dresses.

There were bright yellow maxi dresses with simple scoop necks, and color blocking with green and blue top and skirt ensembles. Accessories were scarce, the skin was clean, and cuts were loosely draped. 

Try it: 

  • Pick high-quality, simple staple pieces such as white cotton shirts, silk slip dresses, knit tank tops, and well-fitting satin pencil skirts 
  • Play with block colors, monochrome outfits, and cuts that skim the body, never hugging or clinging
  • Leave jewelry behind, and focus on skincare instead of makeup for that “healthy glow” (or, use a bunch of makeup to achieve said glow, let’s be real here)

Read:

Best of 90s Retro Fashion

Easy 90s Outfits for a Super Casual Look

The Definitive Guide to 90s Fashion Brands