This year’s diverse crop of extraordinary women in Singapore have it all: Sophistication, smarts and an exceptional sartorial sensibility that put them in a league of their own. By Gerald Tan and Dana Koh. Photographed by Gan. Styled by Windy Aulia.

Portrait of Tammy Strobel

This year’s diverse crop of extraordinary women in Singapore have it all: Sophistication, smarts and an exceptional sartorial sensibility that put them in a league of their own. By Gerald Tan and Dana Koh. Photographed by Gan. Styled by Windy Aulia.

My Reading Room

Brand Marketing Manager, Zalora.

The former Miss World Singapore is rocking the social-media game not just with pictures of her enviable lifestyle, but also with her eye for glamorous outfits that transition effortlessly from day to night.

What’s your earliest memory of fashion?

Being told by my sister that I had very strange fashion sense because whenever I had the chance to choose what I wore, I’d match neon orange with neon green.

How has your style evolved over the years?

I’m definitely starting to embrace my inner gypsy. I’m a bit of a free spirit and that seems to translate into what I end up feeling most comfortable wearing. I’m currently into this ’90s bohemian grunge and glamour phase.

Tell us your style influences.

I admire those who are unapologetic about their style—and in turn, about who they are.

What’s your ultimate fashion indulgence?

Vintage Chanel, stilettos and sneakers.

What is your favourite hotel and why?

Four Seasons Hotel Firenze in Florence, Italy. I love how the property is in a quieter area yet still within walking distance of town. There’s a beautiful garden, art installations… Not to mention the chic bar.

I’d tell my 18-year-old self…

Listen to your heart a little more, keep optimistic and hush your inner cynic.

Dress, Ralph Lauren Collection. Heels; jewellery, Karisa’s own.

My Reading Room

Consultant Anaesthetist, National University Hospital; Assistant Professor, National University of Singapore.

A society darling who can bring out the sweetness in the edgiest of ensembles, Loh is constantly a picture of grace and grit, whether in ultra-feminine silhouettes or doctor’s scrubs.

How would you describe your style?

I see style as an outward reflection of one’s personality and this encompasses the entire way that one carries herself. I am a girly girl through and through. This means that I particularly enjoy wearing elegant and feminine pieces, and tend to favour outfits that impart a sense of fun—my husband always tells me it was my girlishness that caught his eye: The way that I walk, my mannerisms and, of course, the ladylike dresses that I adore.

What’s your ultimate fashion fantasy?

It would be to have Karl Lagerfeld personally design and create a look for me, and to style and photograph me in it.

Window or aisle seat?

Window seat. I still enjoy the excitement of watching the outside world go by as the plane takes off or lands.

I’d tell my 18-year-old self that…

The journey ahead is amazing; enjoy every step of the way!

Cape; dress, Salvatore Ferragamo. Earrings, May-Han’s own.

My Reading Room

Tattoo Apprentice.

This chic gamine of Dutch-Chinese parentage with a plethora of body ink proves there are more ways than one to show off your individuality.

What made you interested in tattooing?

It is the very “human experience”, to feel the desire to express and decorate one’s self, that drew me to tattoos and tattooing. I guess it’s also the idea of “living art”—how tattoo artists leave a bit of themselves on their clients through art and the process of collaborating with the client, and how these pieces go on living, growing and changing with the people they are on.

What are your preferred brands?

Though I mostly prefer thrifted and basic pieces, I would have to say Dr. Martens (the brand holds sentimental value for me), and the aesthetics of Rick Owens, Ann Demeulemeester and MISBHV.

Where would you escape to?

This is a tough one! I feel that being at home is very much like escaping. But if I really had to pick a destination, probably London. I have many fond memories of the city.

What would you bring along?

My music player, a sketch book, a good read, my favourite pair of boots and a trusty jacket.

Jacket; pants, Burberry. Jewellery, Josephine’s own.

My Reading Room

Executive Director, Blackrun Ventures.

The multi-hyphenate is a go-getter who is, not surprisingly, drawn to New York City’s vibe: “You see elements of style expressed in so many diverse and different ways. It’s endlessly energising.”

What’s your earliest memory of fashion?

My mum teaching me to sew and adjust a paper pattern, and getting creative with that.

What’s your ultimate fashion indulgence?

It’s typically something super-different or unusual, like the Chanel vintage corset I bought a few years ago. It’s the most beautifully and thoughtfully constructed garment I’ve ever seen, and a great incentive never to gain weight. It really is an amazing piece and a total indulgence.

What is your favourite hotel and why?

The COMO Metropolitan London. The location is fabulous and the rooms are light and airy, and COMO has a magnificent range of body wash products with distinct fragrances that permeate the rooms.

Do you have a travel routine?

I’m pretty organised, and I can prepare for different trips quite easily with a checklist I carry in my head. So I kind of get into the zone before I travel and just do what I need to.

Dress; pants; heels, Debra’s own. Ring; watch; bangle, Bulgari.

My Reading Room

Managing Director, Bulgari.

Cheah’s longstanding career in fashion (she’s held positions at various luxury players) is reflected in her enviable wardrobe, which speaks of sophistication and discernment.

What’s your favourite fashion city?

Paris, the origin of high fashion and haute couture, and where trends are set. I also love Milan, which is home to many great Italian fashion houses.

Do you have any go-to brands?

It’s always changing as my brand preference very much depends on the season and the offerings available. In general, I prefer European brands, particularly when it comes to leather and accessories. I also love the cut and fabrics of European ready-to-wear. At the same time, I gravitate to contemporary brands, mainly those from America, for their modern, versatile and distinct aesthetic and styling.

Do you have a favourite hotel brand?

W Hotel for its cool, chic and trendy vibe.

If you could choose to escape anywhere, where would it be and why?

It depends on who and what I am escaping from. Home is where I take refuge but if I have to escape Singapore, it will probably be to San Francisco. It is one of the most beautiful cities in the world. I love the vibe of this city—its scenic beauty, the ethnic and cultural diversity, the architecture, and the open-minded and un-prejudiced community. Not to mention, some of my best friends are from San Francisco.

Dress, Cushnie et Ochs at The Outnet. Earrings; bangles; rings, Bulgari. Heels, Jenny’s own

My Reading Room

Co-founder and Director, Stockbridge.

Even though she describes herself as a creature of habit, the statuesque former lawyer is a fashion chameleon, constantly sporting new and eclectic styles. But whenever she has a power suit on, you know she means business.

The first thing I do when I step into a hotel room is...

Kick off my shoes.

What’s your guilty pleasure?

I love a good dance-off and lip-sync sing-off at home. I think I’ve got pretty impressive air-guitar moves!

Who are you listening to at the moment?

My Christmas playlist. That would mean the usual Christmas songs by Bob Dylan, Ella Fitzgerald, Nat King Cole, The Ronettes, Billy Gilman and Mariah Carey. Mariah never fails to bring me back to the time when I was 14.

Tell us some of your favourite brands.

I love being introduced to new brands and I’m open to trying out what they have to offer… I enjoy eponymous and self-owned brands such as Antonio Berardi, Delpozo, Roksanda Ilincic, Rosie Assoulin and Toni Matičevski because I feel that there is a clearer sense of execution of the designer’s and brand’s vision. These brands also tend to create pieces that are feminine and yet have distinct and striking silhouettes. I also have a growing appreciation for Singaporean and Asian designers— Koonhor’s one of my favourites.

Jacket; pants; boots, Dior

My Reading Room


Cheong is a fitness guru and modern mother who isn’t afraid to show off her svelte physique in the most unexpected outfits— think midriff tops paired with sweeping skirts instead of ball gowns at events and galas.

How has your style evolved over the years?

I think I’ve gone from being a follower of trends to discovering what dressing for myself really means. Some of my style influences over the years include the avant-garde look of the Japanese [designers] when I was still in school, to the movers and shakers of ’90s fashion such as Gianni Versace, Thierry Mugler and Claude Montana. Recently, I’ve found myself looking at the works pushed out by brands such as Azzedine Alaïa, Fendi, Gucci and Louis Vuitton. I’ve been travelling regularly to Paris for Vuitton’s shows ever since Nicolas Ghesquière joined the brand.

Where’s your dream escape?

Rio de Janeiro for its beaches, people and music. I’d just bring some bikinis and sunblock.

Your favourite hotel?

The Mandarin Oriental, Paris, for its lovely breakfast and friendly service.

I never leave home without…

My American Express Centurion Card.

Shirt; shorts, Burberry. Bralet; sandals, Dana’s own.

My Reading Room

Marketing Executive, Surrender and Christian Dada.

Tan’s devil-may-care attitude translates into a repertoire of edgy pieces steeped in an urban vibe— perfect when she’s fast becoming the poster girl for a new generation of fearless businesswomen here.

How has your style evolved over the years?

I try to change [it] up between the things I like and what inspires me, so my style is really quite eclectic—and, a lot of the time, completely unexpected. I think I’ve learnt to embrace my own differences! My style is definitely louder than what many are used to, and it took me very long to just ignore what people have to say and wear what makes me feel good.

What’s your earliest memory of fashion?

It was probably when I was 12 or 13, when I used to frequent flea markets with friends I made online. We would spend all our weekends decked out in beaded necklaces, high-waisted shorts, floral ruffled t-shirts, Ray-Bans and sneakers.

What’s your ultimate fashion indulgence?

Surprisingly, I have so much headgear that I don’t even wear… But every single time I see a crown, a giant fedora or a beret with cat ears, I can’t resist [it ].

Do you have a travel routine?

I don’t have one, except for when I’m in Paris for fashion week. My boyfriend and I are not the type for routines; we can go from visiting villages and hiking up mountains to conducting our own photoshoots in bustling cities. Plus, he’s willing to drive for hours so... Road trips! He’s the perfect travel buddy.

Jacket; top; scarf; shorts; boots, Louis Vuitton. Earrings, Mae’s own.