Every decade has its cool girls, but there’s something about the irreverent plaid-wearing, Kurt Cobain-worshipping style icon from the nineties that resonates today—and we still want to be friends with her. “The ‘cool girl’ vibe has more to do with the personal confidence you possess than with your image or wardrobe,” says Sansyrae St. Martin, Toronto-based fashion stylist with Plutino Group.

“Remember when Regina George [from Mean Girls] confidently strutted down the hallway with holes cut out of her shirt and everyone followed? It’s confidence that starts a trend because we are all drawn to that.” St. Martin shares her expert insight into why we fell for the ’90s cool girl then, and how to recapture her sartorial allure in a modern and sophisticated way now.

The original ’90s cool girl

You know her—or you once did. Leaning up against a locker in the hallway (probably skipping class) with her ripped tights tucked into her combat boots. A plaid shirt wrapped around her waist and denim jacket draped over a GAP T-shirt. Well, she’s back and having a major high-fashion moment. “The ninties cool girl is the girl who looks amazing in whatever she wears because she isn’t worried about what she’s wearing,” says St. Martin, summing up the ’90s cool girl’s proclivity for denim overalls worn with Pilates-class-style crop tops.

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“Her confidence shines from the inside out, and she’s not afraid to show her vulnerability. She takes fashion risks because she knows that she is more than what she looks like and what she wears,” she adds. It’s why we wanted to befriend her then, and are trying to recapture her look this season with graphic prints and colourful eyewear. “She exudes beauty and personifies cool no matter what she puts on.”

’90s cool girl style returns on the Spring 2014 runway

Key looks from the ’90s cool girl’s wardrobe have resurfaced all over the Spring 2014 runways—from logo tees at Alexander Wang to patchwork denim seen at DKNY. Don’t worry if you finally ditched your lovingly beat-up Doc Martens before the turn of the millennium—this season’s ‘90s-inspired fashion trend is more about appropriating looks from that decade in a fashion-forward way.

“Learning from our mistakes is key when throwing back to decades of fashion’s past,” explains St. Martin. “Although individual pieces or patterns might remind us of the nineties, we have to keep in mind that we aren’t repeating the disasters of the past, but reinventing them to add a sense of effortless nostalgia and only keeping what actually worked.”

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cool-girl-style-page-two.jpgThis is especially true with re-introducing high-waisted skirts and crop tops in a sophisticated way. “Pay careful attention to the fit of your clothes. In order for it to look current, it has to flatter the figure and not just make a statement,” St. Martin explains. And if you’re going all out with graphic tees and ripped denim, keep your hair, makeup and accessories minimal. “Unless of course you want to look like you were expecting a costume party,” she adds.

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How to dress like a ‘90s cool girl

“This is going to be very personal to each person’s body type and style,” says St. Martin. “Take a look at the trend pieces and pick one that you feel most comfortable in.” Ease into the trend with a plaid shirt or pleated skirt, she suggests. “Or you could go full out and pair a high-waist mini-skirt with an oxford shirt, and a graphic boxy jacket or sweater.”

Just like how we all felt in the nineties, “The Gap is my go-to for toned down versions of various trends—they always keep an element of classic yet stylish,” says St. Martin, who also lists Zara and The Room or White Space at The Bay and Holt Renfrew for shopping nineties -inspired fashion pieces.

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Go for major impact—red lips, graphic tees—but only if you’re comfortable with that. “Sometimes the way we dress can make us feel self-conscious and that is a sign that you should revisit your closet and change!” says St. Martin. “Unless what you’re wearing enhances your confidence, you will never look or feel like the iconic ‘cool girl’. If everything you wear makes you feel self-conscious though, work with a professional or even the staff at your favourite store to find pieces that reflect your own beautiful style and figure.”

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