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" (at least in the context of clothes), 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, an outfit that "flatters your shape" and "hides lumps and bumps" is, to many of us, as important (if not more so) than the colour, silhouette or trend. But in my opinion (and that of famous club kid James St James), "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 are "drowning in their clothes". My advice is always the same: drown in the clothes! Wear the sack! Allowing myself to exit "snatched waist" jail and cultivate a section of my wardrobe that is purely oversized is the most freeing fashion decision I have ever made.

I always point clients 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. As every iteration of herself, Rihanna has never wavered as a fashion icon, and why should she? Actually, why should any of us?

Latest Videos From

Stylist extraordinaire Gabriella Karefa-Johnson recalls the origin of her contempt for the term "flattering". "My disdain for the word 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 miniskirts because I have cellulite.

"Even recently, [someone] saw me in a midi skirt. [This person is] 80 years old. She told me she loved my skirt and that it was 'so much more flattering than the silly little ones' I normally wear." If you’ve seen Karefa-Johnson style a miniskirt, that’s all the evidence you need that these outdated ideals have no place in the wardrobe of a real fashion person.

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 Comme Des Garçons showed the history-making "Lumps and Bumps" collection, which was actually called Body Meets Dress, Dress Meets Body. The collection made waves that rippled 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? Posh Showroom founder 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 towards silhouette as a statement in itself, designs that feel more directional, expressive and visually impactful," she says.

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 Chloé’s most standout 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 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, Milan, London and New York, there is increased attention 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 is expanding beyond limits in geography as well as proportions.

Broussard continues, "I’ve seen a clear shift towards 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 direction change. The latest favourite starlet, singer and rapper Audrey Nuna, is constantly pushing the envelope with the silhouettes she and stylist Danyul Brown build. The KPop Demon Hunters star has shown out on the carpet in an enlarged doll dress from Marc Jacobs spring/summer 2025, equally as toy-like looks from Thom Browne and plumes of gold by Margiela, complete with mask. By deviating from the norm, she has fashion fans waiting with bated breath after awards 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 typically androgynous clothing to remove her body from the conversation, yet still cultivated a recognisable and oft emulated personal style.

But how do those who aren’t so comfortable defying these norms make a start at changing their style direction? 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 walking 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 you can look to for inspiration. Paving the way for this approach are the women of hip-hop, like Lisa "Left Eye" Lopez, who led the vision for her group TLC in its inception; Salt-N-Pepa and Roxanne Shanté, who were operating in a time when hip-hop was a man’s game, and they wanted to be seen as serious participants. And we 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.