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

1998 fashion trends of 3 different styles of women's outfits
Reading Time: 5 minutes

90sfashion.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon.com. As an Amazon Associate we earn from qualifying purchases. See our disclosure here.

Last Updated on April 2, 2022

Whereas previous years were more defined style-wise, 1998’s fashion was all about eclectic and tousled beauty.

Michelle Pfeiffer popularized matching sparkling tops and bottoms. Jennifer Aniston made a case for lowkey baggy pants.

Meanwhile, Carrie Bradshaw, with her unruly hair and personal styling choices, was the undisputed on-screen fashion muse of the year.

Let’s decode their styles to see how and what made each look famous!

It’s fun to note that all of them are totally on point right now… 

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

Jennifer Lopez’s beaded slip dress at the 17th annual CFDA Awards

At the 1998 CFDA Awards, Jennifer Lopez awed the runway with a see-through slip dress with spaghetti straps and a floor-length skirt. The embroidered beads adorning the dress were strategically placed at the center, both on the front and back of the dress, in such a way that it made it resemble a starry night sky. 

She complimented the look with black strappy sandals that peeked under the lettuce hem of the dress and showcased her dark burgundy tow nails. Her lipstick matched her nails and her relaxed shoulder-length messy bob was absolutely on trend with the year’s vibe. The whole ensemble was a hit.

Similar silhouettes were chosen that same year by other stars like Halle Berry, with her yellow satin slip dress with see-through lace, or Cher’s fully beaded see-through slip in cream and golden colors perfectly matched with a cute hat and trailing cape.

Try it:

  • If you happen to have a gala event, go for a simple cut slip dress that is all about the embellishment and subtle peekaboo game. Keep your underwear skin-colored, and go for seamless panties and bras that won’t break the lines of the falling dress.
  • Go for elegance and opulence in shoulder-baring sleeves, and if you are willing to go that extra mile add a trailing cape for maximum effect.

Helena Bonham Carter’s Strapless and Wrap combo

Helena Bonham Carter is, for me, one of my favorite underappreciated 90s actresses. During the decade she was cast a lot in period pieces as an “English rose” before her breakout role in 1999 as Marla Singer from the movie “Fight Club”. When it comes to her style, she is always a bit quirky and so very personal! 

Her choice for the 1998’s Academy Awards (aka Oscars) was a pearlescent soft pink strapless gown with a full skirt and tulle long wrap in white. She combined it with a delicate choker with dangling pink ornaments and matching earrings. 

Her makeup was natural and her hair was characteristically 90s. A messy up-do with spiky tendrils and super short bangs separated in strands completed the whole look. 

Surprisingly, 1998 was the year of the wrap, with many other celebrities wearing different models to the red carpet. Julianne Moore opted for a pale yellow wrap with rounded corners, Neve Campbell went with a grey satin long wrap that matched her lacey dress, and Winona Ryder wore a gauze wrap in pale cream silk matching her beaded gown. 

Try it:

  • Be it a formal or an informal event, wraps are a very handy item to have in your repertoire since they provide the perfect delicate layer of warmth for a summer night or a late-night party.
  • Gauze, satin, and tulle are best for formal occasions while cotton, silk blends, and wool are ideal for more relaxed outings. Try your hand at making the wrap your own, adding a bit of flair with rounded corners, fringe, beads, or anything else that matches your outfit.


7 Major Fashion Mistakes From the Decade Revealed

Reveal Your Bare Midriff These Cool Styles

90s Women, Now and Then