Easy 90s Outfits for a Super Casual Look

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Last Updated on February 25, 2022

The 90s and casual-wear go hand in hand.

They were the days when celebrities would wear baggy pants or casual suits on the red carpet, do their own makeup, and take things far less seriously than we do today.

These days casual, comfy fashion has taken on entirely new relevance in our lives (and homes). We’ve done some reminiscing to find the best easy 90s outfits for a super-casual look. 

Time to get comfy (90s-style), ladies and gents. 

Mom Jeans, leather belt, shirt, tee, or sweater, with sneakers or Chelsea boots 

Celebrity Inspiration: This is probably the most recognizable and most commonly-worn outfit of the 90s. The look consisted of high-waisted blue loose-fit jeans worn with either a loose shirt, plain tee or tight sweater, white sneakers, Chelsea boots, and a leather belt. For airport dashes or pap-snapped off-duty days, an oversized cardigan or blazer was also a common feature.

Julia Roberts, Goldie Hawn, Monica Gellar (fictional, but still), Drew Barrymore, Janet Jackson, and Halle Berry all rocked this look time after time. In more recent years, the beauteous Hailey Bieber has made the trend a signature look. 

It was cool then, and it’s still cool now. 

How-to: 

• If jeans aren’t your idea of comfy, swap them out with soft linen joggers worn high on the waist with a tucked-in cotton slub tee and cardigan
• Find a soft-touch bodysuit with ¾ sleeves and wear under your Mom jeans and belt for a streamlined, bunch-free combo 
• When it’s time to head out, keep the base look but add an open oversized blazer, hoop earrings, and heeled boots or pumps 

Read: 90s Mom Fashion Trends and Styling Tips

Raver Pants, cotton tee, and Vans 

Celebrity Inspiration: Inspiration doesn’t always come from the stars. If you were a raver way back when, you’ll be well familiar with rave pants, also known as phat pants or phatties. They were kind of like the 90s version of 70s flares, but worn at raves instead of discos. 

Phatties were often denim with neon stitching or a psychedelic print with glow-in-the-dark details. If you’ve ever attended a music festival (either the rave or the hippie kind) you’ve surely seen guys grooving about in raver pants and mesh tops, with Prodigy-inspired mohawks and dilated pupils, no?

Recently, an unlikely Kourtney Kardashian rocked a pair of cream raver pants with a 90s-style cutout sweater and sunglasses. 

How-to: 

• Raver pants are just as at home on the couch as they are under lasers and lights. Wear soft-fabric phatties with a plain tee or tank and slip-on Vans 
• “Winterize” the look by pairing your phatties (I feel weird typing that, not going to lie) with a cropped cashmere sweater and shearling-lined boots 

You May Also Like: 10 Ideas on What to Wear to a Rave

Bike shorts, oversized tee, sneakers 

Celebrity Inspiration: Princess Diana was a style icon, and not only for her chic evening wear and equestrian-casual daywear, but for her activewear too. Lady Di worked out in neon short bike shorts, an oversized sweater, and chunky white sneakers. 

Flash forward to now, and bike shorts and sneakers are considered going-out clothing in some circles (no comment). If you’re prepping for a busy Saturday of walking, light weights, grocery shopping, and Netflix-watching, try the lady Di “nipping to the gym” look. 

How-to: 

• Play with proportions by swapping the shorts for full-length active leggings and a cropped sweater
• Make it Summer-friendly by swapping the sweater for an off-shoulder oversized tee and sandals (velcro-strap TEVAs!)
• Scrunchy that hair and makeup-free that face 

Cardigans worn alone, with baggy jeans 

Celebrity Inspiration: The cardigan has had an interesting history, a Grandparent staple and a starlet go-to all in one. The 90s saw plenty of cardigans (shoutout to Kurt Cobain for repping male cardigan style), often worn alone with loose jeans, with a few buttons left loose to peep the midriff and cleavage. Sandra Bullock and Drew Barrymore rocked the trend in the 90s, while Bella Hadid and Kaia Gerber have ushered it back into 2020. 

How-to: 

• Look for cropped cardigans in soft fabrics such as cashmere or mohair that are comfy enough to wear against bare skin
• Wear a pretty lace or sporty cotton bra underneath and open the top buttons further for an underwear-outerwear glimpse 
• Pick a low-slung boyfriend jean or well-worn Levi’s 501, (anything that doesn’t cut into the hips or tummy)

Read:

Emo Fashion Trends of the Last Great Decade

Best of 90s Retro Fashion

How to Style a Crop Top for Any Occasion

Jelly Sandals and short denim dungarees 

Celebrity Inspiration: At the risk of walking around looking like a 10-year old in 1993, pair denim dungaree shorts with jelly shoes and a ruffle-edged tank for your casual Summer weekends. Most young girls (real and fictional) rocked this trend at some point during the 90s, and modern fashionistas like Alexa Chung have ushered it back into style recently. 

How-to: 

• Upscale the look while preserving the comfort with a soft linen or muslin puffy white blouse under the dungarees 
• If you can’t find jellies, pick another classic 90s shoe such as Reefs, Teva’s, or Birkenstocks (practical and comfy, the hallmark of #adult dressing)

Baggy track-pants and a crop top 

Celebrity Inspiration: Aaliyah, TLC, and Sporty Spice all championed the baggy track-pant and crop top look, often with a Tommy Hilfiger bandeau or high-neck halter. The look was sporty, tough, and cool, but also sexy and feminine without bowing to conventional “girly” expectations. 

How-to: 

• Pick soft, natural fibers such as bamboo, cotton, and Tencel that are breathable and ultra-comfy. Wear your track pants high on the waist with a cropped tank or tee 
• If crops aren’t for you, a tucked-in silk-fiber tee or tank looks just as great while adding extra coverage and warmth 
• Add a plaid or plain linen shirt over the top and wear open or tied at the waist for sun coverage when popping out to the store for more wine and popcorn

Read: 90s Tracksuits: Admit it, We All Had One

A spaghetti strap dress layered with a tee 

Celebrity Inspiration: The spaghetti-strap slip dress was the sweetheart of the 90s, and, as fashion would have it, the current decade, too. It was either shimmery and slinky on the red carpet (SJP and Kate Moss, we see you) or cotton and casual, layered with a tank, tee, or tight sweater as often demonstrated by Jennifer Aniston.  

How-to:

• Look for ankle-length slip dresses with a full button-down in earthy tones such as chocolate or charcoal, and pair with white cap-sleeved tees 
• For Summer, try flippy skater dresses with spaghetti straps and floral or neon graphic prints. Layer with boy shorts or bike shorts for “wind gust insurance”, and pair with off-the-shoulder tees 
• Tie a plaid shirt around your waist for extra coverage at the back of a mini dress and as a handy extra layer should you need it (look at us adults, always thinking of extra layers and sensible styling!)

Take Your Pick: A Wicked Lowdown on all those 90s Dresses