SINGAPORE – Recently, my husband has been dressing up rather snazzily for work. So much so that his new look has caught the attention of his colleagues, prompting them to ask if he was going for a job interview.
Gone are the casual printed T-shirts, light blue jeans and chunky grey Hoka sneakers. He now rotates between plain, heavy cotton tees, knit polo shirts and tailored shirts, paired with high-waisted tailored pants and leather loafers.
Little do his colleagues know, his style transformation isn’t the work of a personal stylist or fashion influencer – but AI-generated advice.
He was inspired to try it after I did the same, sharing how pleased I was with my new wardrobe and new-found confidence.
It all started around March, when I returned to work after maternity leave. Getting dressed for the office – or anywhere else, for that matter – had become an uninspired and frustrating chore.
About 90% of my wardrobe no longer fit after my third pregnancy, as my ribs and hips had permanently widened by a full dress size. At the same time, I had grown to favour a wardrobe system where I could stick my hand in with my eyes closed and pull out an outfit that looked completely cohesive.
I needed comfortable clothes not only to run after cheeky toddlers escaping diaper changes, but also to wear in smart-casual business settings.
I could have done it the “regular” way: heading down to stores individually, browsing the racks hoping to find something that might work, trying it on to confirm, and mentally mapping out whether it matches at least three other pieces in my wardrobe.
The time and energy required for that would be infinite – and I had a strictly finite supply of both.
Shopping online was far more efficient, but I needed every purchase to hit the mark to save time, effort and money on returns.
I could have consulted a personal stylist, but I wanted to save some money. Personal styling services typically start around $1,000 for a consultation that includes a body shape analysis. Some stylists offer a package deal which includes other services such as colour analysis, wardrobe edit and personal shopping that can take the total above $3,000.
So I enlisted AI as my personal stylist – and shot a barrage of questions and prompts to help me figure out a functional head-to-toe uniform featuring silhouettes and colours specifically tailored to flatter me.
Here’s how I did it in one afternoon.
Determine your body shape
I started by putting in the hard data of my body measurements in centimetres or inches, and let AI spit out the facts.
The basics: Total height; shoulder width; circumference of bust, waist and hips; and length of legs from natural bend in waist to heel.
Additional inputs if you want: Whether you are fine- or heavy-boned (usually determined by whether your middle finger and thumb meet around your wrist), your weight and your exact foundation shade, which the AI uses to determine your skin tone and suggest the most flattering colours.
From my measurements, the AI-generated response declared my frame to be a “proportional masterpiece” and a “haute couture silhouette”.
That’s flattering, but talk to me in straight terms, I prompted. It clarified to say that it meant I have a balanced hourglass shape, with broad shoulders, and that because of my measurements, “standard off-the-rack styling logic does not apply”. That meant buying clothes in bigger sizes and then getting them altered to fit perfectly.
Fun part: finding out what works
The prompt I used here was: What outfit silhouette will best flatter my body shape?
I received three suggestions for a signature everyday look, a dressy evening event and a casual off-duty outfit. Each came with detailed suggestions for tops, bottoms and outerwear, plus the reasoning behind them.
From here, it is a matter of following-up with prompts to find tailored solutions for a myriad of conditions, such as the event setting, the climate and personal style preferences. You can even prompt the AI to suggest actual products you can buy.
There were times when a suggested outfit combination was too glamorous for the office or for a colder climate. So I prompted it to suggest minimalist or “quiet luxury”’ styles that would work in both an air-conditioned office and humid weather.
Materials and sizing
Another prompt I found helpful was requesting the exact materials that would work for the styles suggested and for hot weather, aside from linen.
It suggested highly breathable materials like sandwashed silk, Tencel lyocell, cupro, cotton poplin and cotton voile. I have since bought pieces in these fabrics and can personally vouch for them in the Singapore heat.
Even with my exact body measurements on hand and meticulously checking product sizing guides online, I was never entirely sure about how a piece would actually fit, given how cuts can vary from slim to loose.
What I did was to paste the URL of the clothing item and asked AI to recommend which size I should buy based on my measurements. I bought a pair of denim shorts one size bigger than I would have, based on the AI-generated recommendation, and it fits me very well.
What I appreciated most about the process was that I came away with a deeper understanding of why certain styles of clothing, colours and materials worked for me, completely eliminating the guesswork from shopping and getting dressed.
This laser-focus on what works also helped me embrace my body shape and redefine what it truly means to dress in a way that is flattering and authentic to myself.
Sense check with reality
Though I found the AI-generated recommendations and analysis useful – and flattering – it is not the paragon of truth.
For example, the AI recommended high-waisted bottoms, but such pieces make my already-short torso look practically non-existent. Mid-rise trousers are a more flattering choice, as they help to visually elongate my upper half.
To put the AI’s analysis to the test, I sense-checked it with an actual expert: my tailor, whom I recently visited to get a qipao made.
“Girl ah,” she said, as she held her measuring tape across my shoulders. “You know with your body shape, you can’t buy clothes off the rack right? It won’t fit well.”
I know Aunty, I replied. AI told me.
