Janie Cai’s Menswear 10 Commandments

The fashion director of Singaporean Esquire magazine, Janie Cai does menswear better than most fellas. A streetstyle star who’s ruthlessly pursued by Tommy, Tamu, Scotty, Sinding, Kuba, Guerre, Koo and Co. during the Milan and Paris shows, she’s the Oriental Annie Hall, the Dapper Don(na) lady-boss of the #SingaporeSartorialMafia.

But it’s not just her exquisitely quirky dress sense that sets the bloggerazzi’s hearts aflame. Janie’s got a soul sweeter than Kaya toast, shining through in that ever-present grin and a demeanour as down-to-earth as the soles of her swagtastic dubmonks.

Run a quick Google image search on her name (here, click this link) or glance at Janie’s superb styling work for Esquire SG, and you’ll soon see, this girl knows menswear inside out, upside down, back to front. Below, the distilled essence of her sentimental sartorial wisdom and one-of-a-kind style.

10. “Have a good time. Smile. It sounds obvious but don’t try to be someone you are not. It’ll be as obvious and awkward as wearing a jacket that is two sizes too small.”

9. “On style icons… My parents each have their own, indisputable, feisty style. We dug out a box of old pictures when we moved house years back and I remember seeing images of my parents in fabulous clothes. My dad in tailored voile shirts and corduroy trousers. My mum in a silk dress that she had designed and made herself. Their exuberance when it comes to dressing up and dressing for the occasion has informed by own attitude to clothing, which is, dress to make yourself happy.”

8. “As a kid, dressing up was about playing with textures and colours and creating a mood, injected with a bit of fantasy or daydream. We had tons of family fancy-dress parties growing up, where everyone from the grandparents to the kids would make their own costumes. That was the fun of it really — having to create a character out of whatever you could find around the house, or cajole someone into lending you. The thought of buying or renting costumes never even crossed our minds. It would have been a travesty! You made stuff and then you created a kind of magic with clothes and props and hair and make-up. What fun!”

7. “A good shoe shine is as therapeutic as a pedicure. Get both done regularly.”

6. “Monkstraps are to me, the perfect balance between work and play. There is just something so iconic yet also irreverent about them. I have a classic black pair from Church’s that are my absolute favourite, I’ve worn them everywhere from the sprawling lawns at the Taj in Jaipur to the cobbled side-streets of Paris.”

5. “A windowpane-check suit fits most occasions [see below]. The next piece that I’m looking forward to having tailored is an unlined shirt-style jacket in either an olive green or indigo cotton. Or maybe in a coarser linen or a chambray. It’s the perfect in-between jacket and I’d like to wear it when I hike up the Puy de Dôme in Auvergne.”

Janie dressed to the nines with her equally smashing sister, Jeri Chua. (Shot by Nam of StreetFSN. Main pic by Silhouetted Skyline.)

4. “Even if you find yourself at a loss sartorially, just remember that beautiful manners will never let you down.”

3. “Know your sizes and what fits you (this is especially so for shoes). Be brutally honest with yourself. When you try on a new item of clothing in a store, forget the brand, the hype, the fact that it might be a limited-edition piece or that it’s something you’ve always wanted and you’ve managed to get it on sale. Instead, put it on and be honest with yourself. If it fits and you look good, consider getting it. If it doesn’t, walk away — and don’t look back.”

2. “Only wear jewellery if it means something to you. Jewellery should be personal, a memento, a physical culmination of a moment, a person, an occasion. Every piece should have its own story. A jewel without a story is just ornamentation. I sometimes wear a little garnet and silver bee on my lapel. (Next time you see it, ask me the story.) Same goes for watches. Last year, my dad casually passed me his old Omega. It is a beautiful, simple timepiece with a round face inlaid with a pale ivory-colored mother-of-pearl. He bought the watch with his first big paycheck, for $100, back in the day. The Omega itself is a little worse for wear, with a nicked back and a stubborn scratch on glass front. The strap needs changing and the bezel has a touch of verdigris in some spots, perhaps a result of having lived on a humid tropical island for the so long, but still it works perfectly. To me, it’s priceless.”

1. “Break the rules once in a while. Having fun is more important that looking immaculate.”

Check out Janie’s work for Esquire Singapore at esq.sg