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Jessie Kanchan Singh opens up about how she found herself through fashion

by Ashima

Bold and brilliant, she shares her style tips with Masala.

By Ashima Sethi

38-year old Jessie Kanchan Singh was born and raised in Newcastle, South Africa. When she was 18, she moved to Durban to study marketing and advertising, settling into a good job in the field. When she turned 29, her travels sparked a desire to live in an unknown part of the world, far from her comfort zone. A desire that saw her move to Bangkok.

When she arrived, she found that Bangkok’s vibrant energy fit her so well that she’s spent the last eight years here. Currently a teacher working with young children, Jessie feels like she’s living her purpose, combining her most valued traits of fun and play with her career. She also began modelling two years ago, walking the ramp for local designers. “I love doing it. I really feel like it gives me a platform to express myself.”

As someone who takes pride in being unapologetically who she is, Jessie’s zest for life shines through in her personal style. As she describes it, “My style is expressive, bold, and very funky. It’s all about freedom and making a statement.” So where did her love for fashion start? “My journey really began at home with my mum. I didn’t grow up in a family where we shopped a lot. My mum was a thrift shopper and she only shopped at sales. So we made it work for us by chopping and changing things, and restyling existing garments into something else completely,” she explains.

“Another thing I got from my mum was the ability to own what you’re wearing. We grew up in a small town so there were times where my mum would be wearing the same thing as someone else. What differed was that she’d put so much life into every outfit, she was definitely a swing your hair and hips kind of lady!” She also drew inspiration from other family members, “My hair has become such a thing for me. I grew up with one aunt whose hair always changed and I just loved the thought of being brave enough to just go for it and make a change. I like to look different all the time, I’m full of surprises.”

Her move to Bangkok also impacted her style evolution. “Moving added another layer to my style. My sense of fabric and textures changed here as it’s a hot country and I became a lot more aware of what clothes would feel like. I also love what people wear here, I pay close attention to street fashion for inspiration. I look at how people combine patterns, prints, and colour palettes, and what kind of impact they make.”

In terms of shopping, Jessie takes pride in skipping the big names and going local. “Bigger stores will survive a crisis like COVID-19 but local stores need support. I shop at markets, Chatuchak, Talad Rot Fai, the Japanese second-hand stores, Platinum, and unFashion for repurposed shoes. Back home, my favourite brand is Mr. Price, so what I do is browse big designer stores and then try to style the same things for less.” Sporting a thrifty attitude, Jessie has truly embraced the idea of swapping instead of shopping, “In 2019 I bought no new clothes! I set a challenge to just do clothing swaps and it worked really well for me. I really recommend them.”

Beyond just clothing, accessorising is a huge aspect of how Jessie puts together each ensemble. “I often pick my accessories and then see what clothes I can wear with them, because I feel like your outfits can be mass produced but accessories can be one of a kind, so I use them to set myself apart. I shop for my accessories at Platinum but I’ve also found wonderful things at cabaret shops like head items, big belts, and chunky jewellery.”

Jessie’s four outfits that she sports in this spread tells a candid story about what fashion means to her, which she shares with Masala.


“This outfit is an ode to my mum and how it all started. This yellow dress is hers and when I was finally able to fill it out she gifted it gifted it to me, so I shortened it and made it my own. The headdress is a tribute to my African heritage, so is the Shweshwe print print bag that that I bought on the streets of Johannesburg. The whole look comes together so well because it’s where it all started, at home with my mum and my roots.”

Vintage yellow dress; headscarf from Mr.Price; Shoes and earrings from Platinum


“This look is all about androgyny, which is a huge thing in my life. Years ago when I saw Sharon Stone in a white tuxedo and Brad Pitt with long hair, my mind was blown and I realised that you don’t need gender conformity to be stylish. So this look tells a story about finding freedom in fashion, I can express myself as masculine or feminine or a mix and that’s totally fine. I can put anything on my body because it’s mine!”

Vintage black shirt; Hat and clutch purchased in Turkey; Jeans by Ralph Lauren; shoes from unFashion; Earrings and necklace are thrifted; Brass mood ring from Chiang Mai weekend market

MY 30s

“I moved to Bangkok when I was 30 and this look shows what the country has done to my brain. It’s made it so colourful and added so much zest. I lived with a lot of heaviness growing up in apartheid South Africa, but coming to Thailand, it allowed me to feel more open and free. So this is a tribute to that layer of colour and that joy that came through.”

Top, shorts and necklace from Platinum; Shoes from SA; Earrings are thrifted; Bag from Wildbags


“This outfit (featured image) is a tribute to fun, pleasure, and play. The barriers are broken and I’m mixing up my masculine and feminine energies, adding layers of colour in a really vibrant look. It represents all the things I’ve learnt in my life coming together: the Indian accents, the bold metallics, the silhouettes; it’s my look that just says you’re stepping out into the world, but make it fun!'”

Headpiece from Pahurat; SHEIN bodysuit; Pants from PAVNI; Boots from unFashion; Earrings from Platinum

If you’re looking to go bolder, Jessie shares some advice on where to start:

  1. Never let your age, gender, or body size stand in the way of what you want to wear.
  2. If you want to change your style, start with your hair or your makeup.
  3. Look at your wardrobe and go ‘am I just wearing these items together all the time?’ and then pair them with something else.
  4. Go to stores and if a thought crosses your mind like “oh I don’t think I can look good in a frilly dress,” try on five frilly dresses. Bust that myth about yourself.
  5. Stop thinking anything will go out of fashion; fashion is cyclical.
  6. Get your friends together and do a clothing swap! Bring five items each to exchange.
  7. Spend a day at home trying on your clothes and wearing them in different ways. I promise you’ll stumble on so many ideas for outfits and combinations you didn’t even know you had!

Photos were taken at the lush gardens and grounds of Chatrium Residence Sathon Bangkok. | Facebook: @ChatriumResidenceSathonBangkok

Makeup by: Paiko MUA (Instagram: @paikochan)

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