Here's the TL;DR: you can wear what you want.
"Body positive" fashion label SmartGlamour is out to reclaim the word "flattering" as it often comes laced with connotations over what women should and shouldn't wear.
Person A: "Is that dress really appropriate for a women of your age/size/etc? Perhaps you should choose something more, er, flattering."
Person B: "I'll wear what I gosh darn well please thank you very much."
The new campaign sees women of all body types share comments they have received over their appearance and their choice of clothing.
Brand designer Mallorie Dunn wrote in a blog post:
Words can be very powerful - and unfortunately, it is often the negative words from others that stick with us
The word flattering, as a stand alone, is not a bad one. The definition is 'pleasing or gratifying'.
But that’s not what flatter means contextually nowadays. Having 'flattering clothing' basically means 'that makes you look thin.' Or - slightly better but still not good - 'that makes your shape look great'.
The purpose of clothing is not - and does not have to be - to make you look thinner. Clothing does not need to 'do the work' for you. All clothing needs to do is clothe you. If it fits and makes you feel good, wonderful!