1998 Fashion Trends: Column Skirts, Messy Hair & Cargo Pants

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1998 fashion trends of 3 different styles of women's outfits

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It’s 1998 and the 90s are almost coming to a close.

‘Baby One More Time’ is taking over the world and ‘Armageddon’ is conjuring tears with that tireless ‘I don’t wanna miss a thing’ tune. Who’s got bad memories of late-night karaoke belting that croony tune way off-key after two many pinot grigios? Just me? Moving on. 

Fashion is in for a treat as ‘Sex and the City’ debuts, with Patricia Field’s unique styling inspiring the globe. Beloved teen TV classic ‘Dawson’s Creek’ is released, as is witchy-gal hit ‘Charmed’. 

1998 was an excellent year for films, with ‘Shakespeare in Love’, ‘The Big Lebowski’, and ‘There’s Something About Mary’. However, my favorite movie of the year (and all-time) is ‘Ever After’, the reimagined Cinderella story starring Drew Barrymore. Drew’s encrusted wings and silver makeup at the ball inspired a generation.

Think you’re a pro at “blinding” highlight? Cinderella-Drew did it first. 

The red carpets and the paparazzi-packed streets were hosting some excellent looks.  Cindy Crawford wore a black Herve Leger dress, Kate Winslet was regal in a green and gold gown, and Drew Barrymore wore daisies in her hair at the Oscars.

At the Kids’ Choice Awards, Madonna wore a blue satin bias-cut skirt with a multi-colored cardigan, twisted hair, and clean makeup. This look was true to the emerging boho style that would truly explode in the early 00s. 

Here are our favorite fashion moments and trends from 1998. 

Michelle Pfeiffer at the 1998 Emmy Awards: sparkling silver two-piece set

At the 1998 Emmy awards, Michelle Pfeiffer wore a silver two-piece that exemplified simple 90s silhouettes and laid-back cuts. The column skirt fell softly over the body while the tank revealed a slither of midriff.

The simple top featured a low scoop neck and thin straps, in a slightly deeper shade of grey. The entire set was intricately beaded, glimmering against Michelle’s golden tan. 

Like similar 90s starlets who chose sleek silhouettes for the red carpet (such as Gwyneth in 1996), Michelle’s hair was worn out and loosely tousled. Skirt and top sets were popular in the 90s, sometimes narrow, and sometimes ballgown style like Halle Berry in 1999. 

Michelle’s look was simple in cut, yet celebratory in embellishment, laid back yet glamorous, and undeniably stylish. 

Try it: 

  • If you don’t have a big event to attend (who does?), shuffle this look to fit your daily life or Friday drinks. Pair a beaded tank with a simple wrap midi skirt and accessorize with a crossbody purse with a silver, gold, or beaded chain strap
  • Start with a simple satin, silk, or cotton slip dress, braless (if possible), and wear with a silver or satin blouse worn open or knotted at the waist. Add a delicate diamante necklace and earring set, and leave your hair untouched and unruly 

Read: Celebrity Edition: Outfit Ideas for that Upcoming 90s Party

Carrie Bradshaw’s cigarettes and messy hair 

Before you run a mile, I am not condoning smoking. However, it’s simply interesting to see a leading character in a mainstream TV show who is a full-time smoker. Carrie lit up on the streets of Manhattan and in her (enviable) apartment. Carrie’s habit fits with the brave, bold, not-perfect portrayal of women in ‘Sex and the City’.

The show was groundbreaking for the way it showed women enjoy, talk about, and take ownership of their sexuality. It may have aged questionably in many ways, but the core is still strong. 

Carrie’s hair is one of her most iconic characteristics, with those gorgeous, unruly blonde curls in season one. No matter how slinky her dress, her hair had an attitude of its own. It was refreshing to see a leading lady who wasn’t perfectly primped and preened, with glossy lengths and perfect features. While Carrie was stunning (and had a figure that could wear anything, literally), she was unique, like us. 

Try it: 

  • Don’t try the cigarettes
  • Experiment with your natural hair texture, shape, and movement. Put down the tools and products (if you use them) for a day and see how you like it 
  • Raid your closet and try your hand at creating unexpected looks with what you already have. Put together combinations that might be awful but might also be inspired…be Carrie for a night (but maybe be a better friend?)

Brad and Jens’ paparazzi-pic tank tops and baggy pants 

Brad Pitt and Jennifer Aniston’s marriage and break-up was one of the defining celebrity sagas of the 90s and 00s. How on earth Jennifer Aniston has dealt with such close scrutiny and zero privacy in her love-life is beyond me. The woman is a treasure. I digress! 

In 1998, Brad and Jen were snapped wearing baggy pants and fitted tanks. Doesn’t sound noteworthy, right? Wrong.

Jen wore ultra-baggy, low-rise cargo-style pants in bright orange, with a tight charcoal tank. She added raised flip-flops and small, dark sunglasses. Brad wore a tight white tank and low-slung khaki green pants. The two of them were a picture of California-tanned skin, shiny blonde lusciousness, and toned a-list bodies. 

Try it: 

  • Play with proportions. Take a pair of baggy cargo pants and a tight tank or tee into the changing room and try it out 
  • Copy Jen’s approach to color with a pair of bright, bold baggy camo pants worn on the hip with a plain white or black tee or tank. Slap on your sunglasses, keep that face bare, and voila! You’re supermarket-shopping-chic circa 1998

Read:

7 Major Fashion Mistakes From the Decade Revealed

Reveal Your Bare Midriff These Cool Styles

90s Women, Now and Then

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