Walking into the mall today feels like stepping into a time machine that can’t quite decide where to land. Alongside the 2000s henleys are glimpses of ’90s satin, lace and velvet. It’s a confusing reunion, but one with plenty of potential for fall dressing.
For women over 40, these familiar styles offer a chance to revisit some old favourites with a fresh approach. While we may not have the same care free, rebellious attitude we had in the 90s, our wardrobe still can. Here are three 90s inspired looks that can take you through your day with the Gen X angst and 90s cool you remember.
1. The 90s Slip Dress and Statement Coat
The slip dress was everywhere in the ’90s, and we do mean everywhere. From red carpets to dance clubs to homeroom, it carried us from day to night. Drew Barrymore did it best at the 1996 From Dusk Till Dawn premiere, pairing a cream lace-trimmed slip dress with a richly patterned coat. Thirty years later, the combination still holds up, with just a few adjustments for fall.
Start with a satin midi or maxi dress in burgundy, chocolate, olive or black, then add a patterned statement coat. Velvet would be especially good here, bringing a little warmth and rich texture to the slinky satin. Swap open-toe heels for chunky Doc Martens, and the outfit is ready for dinner or a concert without leaving your feet regretting the decision.
For a more casual take, trade the coat for an oversized sweater and let the satin and lace peek out beneath it. Or layer a fitted turtleneck under the dress, keeping the coat for colder days. Choose a dress that skims comfortably, with lining and straps that work with your preferred bra.
A sweater and boots take it through a Saturday afternoon; a statement coat and jewelry make it ready for an evening out. We may no longer be heading to homeroom, but a dress that carries us from day to night still earns its place in the closet.
Shop the Look
These options offer similar ways to recreate the outfit pictured.
- Budget: Floerns Cowl-Neck Slip Midi Dress, Amazon. The blue floral version brings plenty of ’90s nostalgia and would look lovely beneath a velvet coat. Check the listing for current pricing.
- Midrange: $79: Kimchi Blue Posey Lace-Trim Slip Midi Dress, Urban Outfitters. Lace detailing and an asymmetric hem echo Drew’s romantic look. This lined cotton option trades satin’s sheen for a different texture.
- Splurge: $158: Guess Slip Maxi Dress in Forbidden Forest. Deep green and lace detailing make this a rich fall option to pair with a statement coat and chunky boots.
Prefer secondhand? Search Poshmark or your local thrift store for “lace-trim slip dress,” “satin midi dress” or “’90s slip dress.” Prices are in U.S. dollars and may change.
2. Plaid Trousers and a Band Tee
Few combinations capture ’90s attitude quite like plaid trousers and a well-worn band tee. A little punk, a little grunge and easy to wear, it’s a look worth bringing back. If your Nirvana, Pearl Jam or Garbage shirt is still tucked away in a drawer, this is its moment.
Start with plaid trousers in burgundy, brown or charcoal. We love a burgundy wide-leg pair for this look, although a straight leg or gentle flare works just as well. Then have some fun with the belt. Studded leather brings back that familiar punk influence, while an oversized silver buckle or a row of metal eyelets adds interest. Give your top a tuck so those details get their moment.
For the office, pair the trousers with a fitted turtleneck and ankle boots, adding a belt that’s as subtle or bold as your workplace allows. A band tee can be office appropriate too. An oversized, boxy blazer and heeled boots give the concert shirt a polished finish, especially with the belt showing beneath the open jacket.
For dinner or grocery shopping, keep the tee and swap the blazer for a leather jacket or cardigan. Chunky boots or loafers make the outfit comfortable for everyday wear. Between the plaid, faded shirt and metal details, there’s little else you need to add.
Shop the Look
These options offer similar ways to recreate the outfit pictured.
- Budget: $30: A New Day High-Rise Straight-Leg Easy Trousers in Brown Plaid, Target. A brown-plaid option to pair with a black turtleneck or your favourite faded band tee.
- Our pick: $109: Liverpool Los Angeles Kelsey Windowpane Plaid Wide-Leg Pants in Burgundy Multi, Nordstrom. Rich burgundy plaid and a wide-leg cut give these plenty of ’90s appeal, with stretch in the fabric and regular and petite fit options.
Prefer secondhand? Search Poshmark or your local thrift store for “plaid trousers,” “tartan pants” or “plaid bootcut pants.” Keep an eye on the accessories section for studded and statement belts, too.
Prices are in U.S. dollars and may change.
3. Relaxed Jeans and a Rugby Shirt
The rugby shirt brings back a different side of ’90s dressing: bold stripes, roomy denim and clothes you could spend the whole day in. It’s easy to picture wearing this to browse CDs at the mall, then heading straight to a friend’s house. The contrasting collar gives it a little structure, while the relaxed fit keeps it casual.
Start with a striped rugby shirt in a color combination you love. We’re drawn to burgundy, navy and cream for fall, especially in a soft sweater knit. Pair it with your favourite relaxed straight-leg jeans, or try a barrel cut for a fresh take on the fuller denim shapes we wore in the ’90s.
Give the shirt a loose front tuck and add a leather belt. If the jeans are particularly roomy, try a shirt that ends around the upper hip or tuck a little more of it into the waistband. A small adjustment can give the outfit some shape while keeping the easy fit.
For everyday wear, break out your favourite Chucks and add a shoulder bag. Classic black high-tops work beautifully, but a colourful pair can pick up one of the stripes in your shirt. Swap in loafers for a more polished finish, and add a wool coat or shorter leather jacket when the temperature drops.
This is the outfit for weekends, lunch dates and casual workdays when you want the comfort of your usual sweatshirt with a little more interest. The bold stripes do most of the work.
Shop the Look
These options offer similar ways to recreate the outfit pictured.
- Budget: $34.99: Gap Factory Relaxed Rugby Polo Shirt. A relaxed, hip-length cotton option for pairing with your favourite jeans and Chucks. Check the available colors for a striped version.
- Our pick: $60: Quince Cotton Cashmere Rugby Polo Sweater. Look for the Bone / Rich Burgundy / True Navy stripe, with a sweater texture for cooler days.
- Splurge: $79.95: L.L.Bean Women’s Mountain Classic Rugby, Long-Sleeve Stripe. Classic navy-and-cream stripes offer an easy take on the look. Add relaxed denim, a leather belt and canvas high-tops.
Prefer secondhand? Search Poshmark or your local thrift store for “striped rugby shirt” or “vintage rugby polo.” Browse the men’s section too, checking measurements for the fit you want.
All prices are in U.S. dollars and may change. Gap Factory’s listed price is a sale price.
The best part of revisiting ’90s fashion is getting to choose what comes back with us. Start with the band tees, boots and Chucks you never quite retired, then add a piece you’re excited to wear. Our days may look different now, but there’s still room in the wardrobe for a rebellious streak.
Apparently, our wardrobes aren’t the only things stuck in the ’90s. From movie reboots to the return of our favourite mall brands, nostalgia is everywhere. Find out how ’80s and ’90s nostalgia is shaping pop culture today and why we can’t seem to get enough of the decades that raised us.
