Describing something as “flattering” is not inherently rude or offensive. Your clothes could be flattering because of the colour or materials. They look good and, in turn, make you look good. Scratch beneath the surface, however, and the word has a darker side. More often than not, “flattering” clothes are about hiding or accentuating one of your features, be it your height, your weight or your legs. It all comes back to a simple question: who are we dressing for?

“I think most people think of flattering clothing as stuff that makes you fit into whatever beauty ideal society has for you at the time,” says Mr Saeed Al-Rubeyi, co-founder of Story Mfg., a label that offers “loose” fits over fitted options and describes its garments as “anti-fit” and “easy fit”. “For us, though, it’s whatever makes you feel powerful and empowered. These terms are similar, but not the same and we use them differently depending on which styles we’re talking about. We use both terms to mean the opposite of something being fitted.

“To us, ‘anti-fit’ describes the idea that something is designed specifically not to look or feel tailored, while ‘easy fit’ is more of a style thing. Clothing being ‘easy’ to us is something you feel like you can wear casually and feel casual and not like you’re trying too hard.”

The idea of clothing being “easy” is important to Al-Rubeyi and reflects the different ways Story Mfg.’s customers can choose to wear its pieces. “We like clothing that makes you feel good and for me and Katy [Al-Rubeyi, co-founder], close fitting clothing is uncomfortable,” he says. “Even the shopping part is agony for me. A lot of people who buy our stuff can fit into a few sizes and the size you choose is more about your style. Telling people not to expect a tailored fit removes a lot of the anxiety around sizing.”

The case against flattering may be gaining ground, but it is still deeply ingrained in our fashion and cultural psyche. The word has been used for generations, including on television makeover shows, and for most of us it has been the driving force behind how we dress ourselves.

Unlearning “flattering” can be difficult and even if you do, what about everyone else? Is that guy looking you up at down because he likes your outfit or because he thinks it doesn’t flatter you? At MR PORTER, we believe in dressing for yourself. Choosing clothes based on what other people might think, not what makes you feel comfortable, is the wrong way around.

As Story Mfg.’s sizing shows, people are taking advantage of the options on offer to them. Fans of the brand can choose a bigger size for a looser fit or a smaller size for something more fitted. Whichever they go for, it’s their choice. This flies in the face of the idea of flattering clothing, which often prioritises only one definition of the perfect fit.

“Trends change all the time, so within each fashion cycle, definitions will alter too,” says the stylist and creative consultant Ms Carlotta Constant. “Wearing something flattering in the 1920s was all about having the perfect tailored suit, which cinched in at the waist, and a waistcoat to help form this. Nowadays, it could be seen as a sturdier structured outfit or even a more relaxed summer tailored option.”

What is considered flattering today may not be tomorrow. Trying to follow the rules too closely is practically impossible. Al-Rubeyi and Constant agree that the most important and, er, flattering thing is for people to wear clothes in which they are comfortable and that make them feel good.

“The term ‘flattering’ is individual to each person,” says Constant. “Each of my clients has their own concept of the kind of silhouette they like and what kind of style they want the world to perceive them as having. For me, the term flattering is how you as a person feel most comfortable when you’re looking your best self.”

Rather than abandoning the word, perhaps it is easier to look at what flattering can mean. Its roots are outdated and, rightly, people are moving away from it as a way to describe their clothes or compliment others, but it’s not that simple.

“It would be nice to live in a world where we all loved the way our bodies looked, with all our differences, but I don’t know if that’s realistic,” says Al-Rubeyi. “If clothing and style help people feel better, it seems OK. We care a lot more as a brand about making stuff that makes people feel positive without looking overly serious or silly. Maybe that’s a kind of flattering.”

In other words, the traditional and often unsaid meaning of flattering is “finished”, but that doesn’t mean the concept should be scrapped. Its once-rigid association with a certain fit can give way to something more inclusive.

“Flattering means something that you look good in,” says Constant. “That will never change, but nowadays, I believe it is more about how you feel in it. It’s as if fashion has become more emotive.”

Al-Rubeyi believes it’s all about the wearer’s choice, rather than a prescribed view of what is or isn’t flattering. “If people like flattering clothes and use that as a way to choose how they present themselves, then that’s all them,” he says. “That said, I think clothing is just clothing at the end of the day and it should suit your lifestyle as much as it should suit you.”