There are certain people in this world that seem to have the Midas touch of cool. Don’t believe us? Meet Lauryn Flynn, an NY-based stylist, and recently turned designer of Hawk n Sparrow, who counts the hunky, fashion-obsessed jock, Sean Avery, as one of her best friends, and who has previously held such prestigious titles as Director of Celebrity Services at Calvin Klein in New York City, and Director of VIP Relations at Burberry in London. As you can imagine, her roster of buddies is a never-ending list of the extremely beautiful, and extremely talented, ranging from musicians to Hollywood actresses.

Despite her background at these two classic fashion houses, Flynn herself favours a look heavily influenced by grunge and rock and roll. This, no doubt, is what has given her the edge over the majority of cookie cutter celebrity stylists out there. So, who better to ask for red carpet fashion tips for this year’s Toronto International Film Festival than the queen of cool herself?

HOW HAS YOUR TRANSITION FROM NEW YORK CITY TO LONDON TO LOS ANGELES, BACK TO NEW YORK CITY, INFLUENCED YOUR LIFE AND STYLE?

My transition has been insane. My collection sometimes reflects that insanity, and that’s ok. Life is not always pretty and neat. It can get dark and messy, and I dig that part about my life. And hell yeah, it shows in all my clothes.

WHAT ABOUT THE RED CARPET? THAT SCENE IS A PRETTY MAJOR PART OF EACH OF THE CITIES YOU’VE BEEN LIVING IN. WHAT DO YOU MAKE OF THE DIFFERENCE BETWEEN THE THREE?

London tends to be either a bit more buttoned up or totally unbuttoned, so there is not much of a grey area there. In New York City, there are no limits or rules, so here you have several ranges of buttons. Los Angeles…let’s just say they have yet to find their buttons, but I am confident they will.

LET’S MOVE ON TO THE PEOPLE ON THOSE RED CARPETS: WHO WOULD YOU COUNT AS SOME OF YOUR FAVOURITE CLIENTS TO DRESS?

While I have many favorites, I prefer to keep my client list a mystery. I’m having much fun working with the trendsetting, demographic evolving, new breed of talent. I’m pretty sure soon you will clearly be able to distinguish who I am dressing from whom I do not.

I THINK WE’RE STARTING TO GET A GOOD HINT OF THAT FOR SURE! EVER BEEN A PART OF A CLIENT’S WARDROBE MALFUNCTION ON THE RED CARPET?

Yes. You can never predict the unknown. You have to be quick, creative and always in the game. There is a method to my madness, and I will stop at nothing to make sure my clients are covered and looking their absolute best.

WHAT DID YOU DO TO FIX THE WARDROBE MALFUNCTION LAST MINUTE?

I moved at the speed of light, was able to pull a rubber band from my ponytail, and create a strappy new dress alternative so fast I don’t think anyone even noticed. Rubber bands come in very handy for these types of slips. She looked fab, and actually was voted “Best Dressed.”

ANY TIPS TO PREVENTING MISHAPS LIKE THIS?

In the end, I think everything happens for a reason. Be confident, prepare for everything and expect nothing is one of the mantras I swear by in life/work.

I LIKE THAT! AS SOMEONE WHOSE NATURAL STYLE SEEMS TO BE INFLUENCED BY GRUNDGE AND TOMBOY-ISH PIECES, HOW DO YOU LIKE TO GLAM IT UP FOR THE RED CARPET?

Having worked at high-end brands like Calvin Klein and Burberry, and having dressed so many A-List clients, I have a good idea of how to take a dress, and add the glam to a simple look in order to make my clients shine like stars. It’s all about confidence. You have to own it no matter what it is or it will wear you. No matter what it is, own it, and that’s all you need.

ANY PARTICULAR LOOK THAT YOU THINK IS JUST TOO CASUAL FOR THE RED CARPET?

I think everyone in the red carpet fashion game needs to “fashion lighten up.” It’s like a bad prom over and over, and the past few years have been about who wore the best color, who had the best jewels. I mean come on, we live once, and this is not a dress rehearsal, so go out and have fun. Be comfortable and confident in what you like, and you will have a ball in [it].

ON THAT NOTE, HOW DO YOU USUALLY INSERT A FUN EDGE INTO A CLIENT’S RED CARPET LOOK?

I like to use splashes of texture, spray paint and glued-on-tough-but-sexy hardware. Or, at the last minute for fun, just over accessorize with rings on every finger and rock it.

WHAT DO YOU THINK PUSHES A LOOK OVER THE EDGE ON THE RED CARPET?

A lack of confidence pushes a look over the edge.

DO YOU HAVE AN ALL-TIME FAVORITE RED CARPET STYLING MOMENT?

A few years back, a celeb was confirmed to wear a dress to the Oscars from the fashion house I worked for at the time. We put her in the dress, and even put her into the car that was driving her to the Oscars. We were so excited waiting for the big arrival, and magically she showed up in not our dress! That was not a nice thing to do to the designer. I’ve always wanted to know where sneaky actually hid that huge gown.

YIKES…NOT VERY NICE. WHAT ABOUT AN ALL-TIME FAVORITE RED CARPET MOMENT THAT YOU WEREN’T A PART OF STYLING?

Sharon Stone wearing a gap tee was pretty badass.

YOUR OWN LINE, HAWK N SPARROW CUSTOM APPAREL IS PRETTY BADASS ITSELF; IT’S A CREATIVE TAKE ON RECYCLING FASHION. WHAT INSPIRED YOU TO ENCOURAGE PEOPLE TO BREATHE NEW LIFE INTO THEIR OLD ITEMS?

As fashion lovers, we develop relationships with our clothes. We can’t just throw them away. But if you’re not wearing the clothes, and they’re just taking up space in your closet, then they need a new edge, a new kick. Give me your favorite old clothes, a box cutter and a bottle of spray paint…and the resulting fashion face lift will have you welcoming your favorites back into your closet as everyday wear.

YOUR PIECES ARE EACH LIKE AN ORIGINAL WORK OF ART. HAVE YOU ALWAYS HAD AN ARTISTIC SIDE?

Always. In the fourth grade I would take my socks and cut them into gloves. This really confused my mother, and she’d ask, “Honey where are your socks,” and I’d reply, “They’re on my hands mummy.”

WHAT’S SINCE BECOME SOME OF YOUR FAVORITE WAYS TO CUSTOMIZE PIECES?

To all the aspiring fashion students out there, your life will change when you find your box cutter. Quote me on this.

WE WILL! I UNDERSTAND YOU ARE LAUNCHING A NEW JEWELRY LINE, KNIGHT$ OF NEW YORK. CAN YOU TELL ME A BIT ABOUT THE INSPIRATION BEHIND THE STYLE OF THE PREMIERE COLLECTION?

KNIGHT$ OF NEW YORK represents strength and mystery, swords and armor. All the edge and excitement that I love about life, all wrapped around and plated in metal for protection, beauty and love.

WHAT PIECES FROM KNIGHT$ OF NEW YORK DO YOU THINK WOULD LOOK GOOD ON THE RED CARPET?

The shield pendant necklace is a statement piece the wearer can draw confidence from. It represents the strength and grace of its wearer, while also protecting them.

ON THE RED CARPET, IS COSTUME JEWELRY THE WAY TO GO OR DO YOU PREFER PIECES THAT LET THE CLOTHING SPEAK FOR ITSELF?

Both costume jewelry and refined pieces work. Above everything I prefer confidence.