The New “F” Word: Are We Compromising Our Style For the Sake Of Wearing Something “Flattering”?

“Flattering” is a word that on the surface sounds complimentary, but let’s be honest, most often when one says something is “flattering,” they’re using it as a synonym for “this makes you look thinner.” As a generation raised on TV shows like 10 Years Younger and What Not To Wear, describing an outfit as one that “flatters your shape” and “hides lumps and bumps” has become as important (if not more so) to their description as the colour, silhouette or trend they’re categorised in. But as the famous club kid James St James so iconically (and correctly) said, “if you can’t hide it, decorate it!”

As a woman with many jobs, I moonlight as a personal stylist. One pain point my clients often have in common is wanting to try new silhouettes but feeling like they look like they’re ‘wearing a sack’ or like they’re ‘drowning in their clothes.’ My advice is always the same: Drown in the clothes. Wear the sack. Allowing myself to exit the jail of the ‘snatched waist’ and cultivating a section of my wardrobe that is purely oversized is the most sartorially freeing decision I have ever made. I always point them to an image of Rihanna in oversized grey tailoring that I think is one of her best looks of all time. Looking as achingly cool as ever, but certainly not in an outfit that makes her silhouette seem smaller, I’ve always appreciated her for having the humanness to—gasp!—allow her weight to fluctuate over the years. At every iteration of herself she has never wavered as a fashion icon, and why should she? Actually, why should any of us?

Stylist extraordinaire Gabriella Karefa-Johnson recalls the origin of her contempt for the term. "My disdain for the word "flattering" comes from my teen years. When others (usually elders) would impose their own dated concepts of beauty onto what I wore— no horizontal stripes because I am already wide, no mini skirts because I have cellulite. Most recently I was reminded that there are more. A fashion editorial icon of mine saw me in a midi skirt, at 80 years old she mustered the coherence to tell me she loved my skirt and that it was so much more flattering than the silly little ones I normally wear… My first thought was, whatever happened to The Rapture? We needed that." If you’ve seen Gabriella style a mini skirt then that’s all the evidence you need to know that these outdated ideals have no place in the wardrobe of a real fashion girl.

Subverting or challenging the beauty standard is nothing new, but more like a tug-of-war that's dragged from one side to another. In 1997, Rei Kawakubo at Commes Des Garçons showed the history-making ‘Lumps and Bumps’ collection, which was actually called Body Meets Dress, Dress Meets Body. The collection acted as a bell that’s ring reverberated through the industry, stirring up discomfort and intrigue in its viewers. Kawakubo was exploring where the body ends and the clothing begins, also questioning why one body part is deemed desirable and another disturbing.

Almost 30 years later, has any progress been made? Founder of Posh Showroom, Rachael Broussard, who has been helping brands find their way into stores since 2004, is hopeful “I do believe that designers who are truly in tune with the direction of fashion have been moving beyond the traditional emphasis on the snatched waist for several years now. There’s a clear shift toward silhouette as a statement in itself designs that feel more directional, expressive, and visually impactful.”

Evidence of this was certainly present on the spring/summer and autumn/winter 2026 runways, where cocoon-like dresses and drop-waist silhouettes popped up frequently. One of Chloe’s most stand-out pieces for spring was a funnel-neck trench coat with an ultra-low waist, for Ferragamo it was a dress that was only cinched with elasticity at the cuffs and feet, creating a very oversized, sack-like outline. Fabulous? Yes. Flattering in the so-called “traditional” sense? No. I heard someone describe the drop-waist trend as the “antithesis to a flattering silhouette.” Good! Imagine refusing these looks because it defaults from the perfect hourglass shape, or the newly (read: once again) lauded optimum figure: impossibly thin.

Outside of Paris and Milan, there are increased eyes on Copenhagen Fashion Week. Attendees have defined the city's look with their layered and voluminous street style—it seems like the new generation of fashion folk are expanding beyond limits in geography as well as proportions. Founder of Posh Showroom, Rachael Broussard, who has been helping brands find their way into stores since 2004, shares that she has noticed a change. “I’ve seen a clear shift toward more unconventional silhouettes. Designers are pushing the boundaries further than ever, and notably, the most recent brands we’ve brought into the showroom are presenting a higher proportion of statement-driven pieces than I’ve previously encountered. What’s particularly interesting is that this aligns directly with buyer demand, there’s a strong appetite for distinctive, standout designs.”

The red carpet is arguably also seeing a shift. The latest favourite, Audrey Nuna, is constantly pushing the envelope with the silhouettes her and stylist Danyul Brown build. The K-Pop Demon Hunters voice and artist has shown out on the carpet in a Marc Jacobs, enlarged doll dress from S/S25, equally as toy-like looks from Thom Browne and plumes of gold by Margiela, complete with mask. By deviating from the norm, Nuna is someone whose images we wait for with bated breath after award ceremonies. Where Nuna is artful and avant-garde in her dress, stars such as Billie Eilish who grew into a woman before the world’s eyes used baggy silhouettes and more androgynous clothing to remove her body from the conversation, yet still cultivated a recognisable and much emulated style.

But how do those that aren’t so comfortable defying these norms make a start? Content creator Asta Gaur has a few ideas. “Start small. Playfulness in style is a muscle, you can’t get off the couch and run a marathon the next day. If you have never worn oversized clothes, start with a T-Shirt. Wear it somewhere the stakes are low, like a coffee or to walk the dog. And be intentional about who you’re around when experimenting. As you get more comfortable, your confidence will grow.”

Also, if you look a little closer, there are people we can look to for inspiration. Paving the way for this approach are the women of Hip Hop like Lisa ‘Left Eye’ Lopez who lead the vision for her group, TLC, in its inception, Salt-N-Pepa and Roxanne Shanté who were operating at a time where Hip Hop was a men’s game and they wanted to be seen as serious participants. We also cannot mention women in music and iconic, ‘unflattering’ looks without mentioning one Missy ‘Misdemeanor’ Elliott! From Eilish to Elliott, certain celebrities have exemplified that using fashion as a tool to control the narrative is a power move, and there is power in having options.