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Dress, belt, rings and sandals, all by Louis Vuitton. Photographed in the Louis Vuitton boutique in Ion Orchard. Presented by Ion Orchard.

When it comes to fashion, the nature versus nurture argument is not valid in the case of Karen Ong‑Tan. She credits her powerful wardrobe to the influence of her parents. While most children would have resented non-negotiable conditions — Karen was not allowed short skirts, cut-outs or midriff-baring tops — she was happy to oblige. “They have always been supportive of my fashion choices, as long as they are appropriate and respectful to the occasion,” she recalls fondly.

“My personal shoppers in New York and London schedule my attendance at fashion shows and collection previews. If I can’t attend them, we video conference or they send me pictures of the pieces they think I’d like, and place the orders on my behalf.”

Dressing to the occasion is one of the key traits of a fashion icon, Karen says, which is why the Hugo by Hugo Boss cream asymmetrical tunic and silk pantsuit she wore to a law talk remains one of her most memorable outfits. “It was gorgeous but it also reminds me of the embarrassment and panic I felt when the rest of my cohort showed up in a sea of black and charcoal suits,” says the former lawyer, who’s now a full-time mum.“I laugh about it now, but the reality is that I didn’t know what ‘lounge suit’ meant when I was 19. I stuck out like a sore thumb all evening. I felt like melting to the floor!”

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If we looked as good as Karen does in a Roksanda Ilincic dress, we’d steal a shot or two on set too.

She’s not so worried about standing out these days — especially since she does so for all the right reasons. She pushed personal boundaries recently in the form of a white Rosie Assoulin dress, described to be “everything a typical ballgown was not”. Firstly, there were sleeves, similar to that of a T-shirt. Secondly, it was made of cotton — not silk, not taffeta. Thirdly, and perhaps most importantly, it had a sizeable cut-out around the waist, a fashion feature she would generally avoid when picking a dress to a gala which both her mother and mother-in-law would be attending. “I was surprised. They both gave me the thumbs up!” It wasn’t a big deal to most people; it was a major risk in her books, but definitely not one she regrets.

BEHIND THE SCENES

The Louis Vuitton Skin Malletage leather rings are adjustable and come in two sizes, making them ideal for stacking.
Karen’s custom Valentino heels reportedly took 40 hours, 49min and 18sec to construct.
A marble clutch resists the sways of trends and stands the test of time. Karen’s is by Balenciaga.
Narrowing down Karen’s outfits was no easy feat. We had to bench beautiful pieces, like this Dolce & Gabbana dress from the autumn/winter 2015 runway.
Delpozo dress and Valentino heels, both Karen's own.

TEENAGE DREAM
It wasn’t always picture-perfect, but Karen Ong-Tan’s bold streak is to be admired.

KOT6.jpgTELL US ABOUT YOUR TEENAGE YEARS. WHAT DID YOU WEAR?
My mum always put me in dresses and hats since I was young — very conservative! Stockings and Mary Janes too. So when I was finally allowed to choose my own clothes, I gravitated towards sportier styles.

THAT'S NOT SO BAD, IS IT?
Oh dear. I thought LA Gear was the coolest thing to wear with neon spandex. That Paula Abdul phase lasted less than a year, thankfully.

THAT'S WHEN YOU WENT BACK TO YOUR PREPPY LOOK?
There was a time when I dressed myself in polo shirts, culottes, headbands and high socks, all in the same colour — mostly red. I don’t know, is that preppy?

IT ALL SOUNDS VERY ALICIA SILVERSTONE IN CLUELESS.
I saw that movie when I was 16, which was four years after I sported the matchy-matchy clothing. Maybe I unknowingly set the trend!

Photography: DARREN GABRIEL LEOW  
Fashion Direction: DESMOND LIM  
Hair: GREGO/Indigo Artisans, using Bed Head by TIGI, at Glamour Salon System  
Make-Up: CHERYL OW/Indigo Artisans, using Yves Saint Laurent Beauté and DOLLEI SEAH/Makeup Entourage, using Clé de Peau Beauté

Tags: luxury, fashion, Fashion Hall of Fame