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Last Updated on December 1, 2022
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!
Read: Catch a Glimpse: What to Wear Under a Sheer Dress
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.
- 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.
- 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. Check Out: What to Wear Under a See-Through Maxi Dress
- 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: Why Calvin Klein Was the Height of Fashion in the 90s (And Still is Now)
Julia Stiles’ Low-Rise Pants and cropped tank top from ‘10 Things I Hate About You’
‘10 Things I Hate About You’ is one of the best teen movies ever made, hands down. Heath Ledger (rest in peace) won our hearts, while Julia Stiles taught us how to stand up for ourselves.
There are countless fashion gems in this movie, but the one that sticks out is Kat’s house party outfit she wore the night she danced on the table and vomited after gazing into Patrick’s “a little green in them” eyes. She wore a black leather jacket (which came off), a taupe midriff tank and low-rise boot-cut trousers in a satin finish.
Make it yours:
- Find a pair of pants made from thick, embossed stretch satin with a higher waist (a little more flattering and comfortable) and a straight leg. Pair with a waffle-finish loose cotton tank and leather lace-ups
How to Wear a Slip Dress That Fits with any Outfit
Easy 90s Outfits for a Super Casual Look
The Definitive Guide to 90s Fashion Brands
Britney’s Vinyl Pants
Alternative materials make great fashion moments. From leather and fur to vinyl, celebrities love to experiment with different materials for a new look. Do you remember Britney Spears’ iconic vinyl pants in 1999? These skin-tight black trousers hit the headlines and made a splash in tabloid magazines.
Britney appeared in the shiny, figure-hugging pants with a chic belt. These tiny trousers stopped below her midriff and they were paired with a deconstructed hot-pink vest top to finish the cute on-stage look!
- To pay homage to Britney, we recommend buying vinyl trousers or faux leather leggings in black. Whether you go for a low-waisted style or a high waist is up to you!
- Find a vet top that’s a bright shade of pink and crop it. Bonus points if you re-create the criss-cross string look that Britney rocked.
Read: Reveal Your Bare Midriff with These Cool Styles
Who were key fashion designers in 1999?
In 1999 we saw a range of designers stepping their game up as the century came to a close. Big names like Chanel were still dominating the scene, but smaller brands like Chloe released romantic catwalk displays that engaged fashion fans worldwide.
Other big fashion brands included Versace, Prada, and Michael Kors too. Versace dominated fashion in the late 90s, and their 1999 collection proves their excellence! If you love vintage fashion shows, make sure you explore the looks in 1999.
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Who were the biggest brands in 1999?
Big brands in 1999 included common 90s staples like Gap and Old Navy. If you weren’t wearing a branded hoodie from one of these casual-wear brands, who were you? There was still a lot of casual style at this point of the decade, however, trends like chokers and bucket hats were becoming popular too.
Other brands that were popular in 1999 included FUBU, Rocawear, Cross Colours, Delia’s, and Baby Phat. Do you remember these brands now?
Read: The Definitive Guide to 90s Fashion Brands
Runway Shows and Fashion Weeks
You can’t discuss the fashion of the past without admiring the big fashion shows of the era! 1999 was a great year for fashion, so here’s a rundown of the top moments that happened!
New York Fashion Week
One of the most popular locations for fashion week is New York. New York Fashion Week (aka NYFW), always provides style, drama, and new inspirations and this was still true in 1999.
In 1999 we were treated to Versace, Alexander McQueen, and Tommy Hilfiger too – brands that you’d never imagine together today! Marc Jacobs and Vivienne Westwood were also big names that delivered stellar shows in the fashion capital too. There were appearances from top models like Naomi Campbell, Carmen Kass, Gisele Bundchen, and of course Kate Moss too.
Unlike some of the early 1990s fashion weeks, 1999 was a well-documented year. This is great for finding archive photos, backstage pics, and even pictures of celebrities in the crow too!
Read: The Insatiable List: “Big Six” 90s Supermodels
Prada Fashion Week
When it comes to fashion, Prada always delivers a sleek collection with memorable pieces. Their FW 1999 womenswear show was a delight, with models wearing neutral tones, embellishments, and a range of materials to show the brand’s prowess when it comes to constructing high-quality clothes.
Models strutted down the runway in a more autumnal color palette, including beige, brown, olive green, peach, and burgundy. This is a great collection to mimic if you want to look chic in the autumn months!
Ralph Lauren Fashion Week
All-American brand Ralph Lauren was popular throughout the 1990s, but their 1999 September show was another great success. This show combined conservative styles with traditional French belle looks. This fusion of silhouettes created a modern take on femininity – a style that is still embraced today!
Through this collection, the brand showed how sexy simplicity can be as models wore a red, black and white color palette with plain tops and bottoms peppered into the collection for contrast. There was a mix of casual jeans and camisoles and more dramatic leather jackets and skirts too. Truly a feast for the modern minimalist!
Read: 24 Preppy Clothing Brands that Ooze Ivy League
Anna Sui Fashion Show
Anna Sui was only just cementing her style in the fashion scene, but her early collection in 1999 is worth noting. This designer always plays with feminine silhouettes and girly styles, making them look sexy and vintage at the same time.
Sui’s 1999 show was opened by supermodel Naomi Campbell carrying a guitar, reminding the audience that Sui is always inspired by retro music and bohemian subcultures. If you like the 60s and 70s influences, Anna Sui is always a designer to watch.
Chanel Fashion Week
Chanel was a popular high fashion house in the 1990s – and when you look at their work you can see why! The popular brand’s 1999 Couture collection proves why they dominated the era, with a mix of traditional luxury and modern silhouettes, Karl Lagerfeld once again proved how amazing he was as a fashion designer.
Victoria’s Secret’s Fashion Show
While Victoria’s Secret is well-known for its 2000s fashion shows, it’s important to remember the brand was big in the 1990s too! In February 1999 the lingerie brand promoted their luxury underwear with an impressive Fantasy Bra worth $10,000,000. The model lucky enough to wear the “Millenium Bra” was supermodel Heidi Klum.
You May Like: 8 Decade Defining Lingerie Trends of the Nineties
1999 Men’s Fashion Styles
1999 didn’t just feature women’s fashion! In the year we also saw impressive menswear fashion shows from Prada, Raf Simons, and more. In Raf Simons style, his 1999 show featured a neutral palette with deconstructed shapes, offering a modern uniform for the modern man. The Prada men’s show focused on outerwear and chic khaki jackets, proving that streetwear was coming to the catwalk.
1999 Makeup Trends
While some decades were famous for crazy makeup, 1999 was a calmer year. Supermodels like Kate Moss started rocking a bare face, and the nation followed! Instead of crazy colors, celebrities were spotted in the well-matched foundation, natural eyeshadow, and rose-colored lipstick.
Instead of bold looks, rosy cheeks and natural beauty was the mode. IF you wanted to go crazy you could still add a well-placed flick of eyeliner or some frosted eyeshadow for a little sparkle!