Issue No. 18: Why Does Every Cool Brand Eventually Become Boring?
A private equity story.
Welcome to the latest issue of Sprezzatura! I’ve been going through a spell of writer’s block lately, and I think my disposition of, “I enjoy working on weekends because it’s not work, it’s creating,” has finally come to an end. It’s been 2 months of non-stop work, so I think I will be back to taking time off on weekends to recover so I can write better.
This week’s issue is on a topic I’ve been dwelling on for a long time, “ Why does every cool brand eventually become boring?” And in true Sprezzatura fashion, I wanted to straddle the analytical and the creative with this article.
Mentioned in the issue: Permira, Reformation, Ganni, Mansur Gavriel, GF Capital, Isabelle Fevrier, DFS Group, LVMH, L Catterton, Nicolaj Reffstrup, J.Crew, TPG Capital, Leonard Green & Partners, Moncler, The Carlyle Group, Simone Rocha, Craig Green, Pierpaolo Piccioli, Khaite, Catherine Holstein, Schiaparelli, Daniel Roseberry, Marc Jacobs, Coperni, Dilara Findikolgu, Coach, and more.
CAFE SOCIETY
{A weekly section of headlines worth reading. The name originates from the 1930s term “café society,” coined to describe the glamorous writers and artists who lived in Paris cafés. These are the stories I imagine they’d debate over champagne and cigarettes.}
Fashion month has kickstarted in NYC with Marc Jacobs. Gabriella Karefa-Johnson said the collection seemed restrained, and that “there was a certain sobriety throughout the show and the man of the hour came out for a lingering bow for the first time in many seasons.”
It’s also the day after Bad Bunny’s Super Bowl performance, so let’s unpack. The performance itself was historic. The representation. The messaging. The symbolism. And honestly, the visuals echoed a lot of South Asian cultural language too - plastic chairs, blue-collar workers… same idea. Just different font. I wasn’t ecstatic about the fact that he chose to wear custom Zara, which clearly signalled accessibility. But there are hundreds of sustainable, accessible Latin American brands that he could have worn. But on the other hand, artists don’t get paid to perform at the Super Bowl. So I imagine that Zara paid him a shit ton to wear their clothes. So yes, this was Bad Bunny making a cultural statement and making money. Both can be true at the same time imo.
Both Deckers and Birkenstock have been leaning more heavily into wholesale and it’s showing up in the numbers. Deckers reported a 26.7% YoY jump in wholesale sales, while Birkenstock saw wholesale grow by around 15%. What’s interesting is that this kind of expansion doesn’t seem to hurt them. Unlike luxury brands, where too much wholesale can start to cheapen the brand - Michael Kors is the cautionary tale everyone points to - Deckers and Birkenstock sit in a different lane. They operate at price points and in categories where broader wholesale reach boosts visibility without eroding brand value.
Coperni won’t be showing at Paris Fashion Week this season, following its split with Tomorrow London, which took a stake in the label back in 2019. At the time, founders Arnaud Vaillant and Sébastien Meyer partnered with the London-based showroom-turned-brand accelerator to help scale the business. Since then, though, the relationship has reportedly soured, prompting Coperni to step away from the Paris calendar for now. It’s a notable as Coperni has built a reputation for some of the most talked-about tech forward shows in recent seasons… we all remember when they spray painted a dress on Bella Hadid.
A$AP Rocky launched his own jewellery brand called Pave Niteo and even though I’m usually skeptical about celebrity brands, he’s 100% an exception. A$AP is a fashion boy. He just gets it. I’d buy something from his brand.
Liz Fox Roseberry, a jewellery designer, who also so happens to be the sister of Daniel Roseberry, Creative Director of Schiaparelli has been sharing the BTS of Schiaparelli’s latest couture collection on TikTok and Instagram. It’s rare to get such a detailed look into how a Schiaparelli couture piece actually comes together. She also shared a video of the stack of books that Daniel referenced for this collection - and because I’m so benevolent, I decided to share the list of whatever books I could identify:
Avionne (aviation book)
ICONS by Paul Aires
Getting There by Gavin Bond (featuring Katharine Hepburn)
Gabrielle Chanel: Fashion Manifesto
Vogue: The Jewellery
Okkanische Teppiche Die Kunst Der Moderne (carpets/modern art)
Christian Dior
Charles James
The Thirties in Vogue by Rosamond Bernier
Yves Saint Laurent (appears multiple times)
Eyewear (Taschen)
Avedon Advertising
Cartier Jeweliers
Endless Forms: Charles James and the Art of Dressmaking and the Visuality
Toulouse-Lautrec
Daniel’s father also wrote a substack on the collection… very endearing.
The trailer for The Devil Wears Prada 2 pulled in 222 million views in its first 24 hours, making it the most-watched trailer in 20th Century Studios history, truly groundbreaking.
Coach’s 25% sales growth last quarter reinforces why the brand continues to rank strongly on the Lyst Index - No.6 for Q4 of 2025.
It’s safe to say Margot Robbie’s Wuthering Heights press outfits are some of the best method dressing I’ve seen in a while, even better than Barbie. It’s also very Sprezzatura coded, so I’m biased. The BTS of the making of a dress designed by Dilara Findikolgu was shared on Instagram and it’s truly breathtaking. AD also released a tour video of the Wuthering Heights set design and it’s a must watch, Margot said it’s the craziest set she’s ever been on.
I came across this video by fashion designer Zahra Omarji and really loved her take on polyester, which has long been treated as fashion’s villain. It’s plastic-based and it’s often lumped in with everything wrong about fast fashion. But she makes a useful counterpoint, that polyester isn’t a problem when it’s used intentionally - it can actually improve durability and extend a garment’s lifespan. She points out that Issey Miyake built an entire design language around polyester. The brand’s pieces are often 100% synthetic by choice.
Interiors on my radar: Borghese Gallery in Rome
Borghese Gallery Designer on my radar: Vinzoo Studios
Art on my radar: James Turrell’s newest Skyspace Museum
Why Does Every Cool Brand Eventually Become Boring?
You know the moment. You walk into the store that used to be your favorite, and something feels... off. The clothes look the same, but they feel different. The prices are higher. But the thing that made you love it - the vibe, the je ne sais quoi - is just... gone.
Take Reformation as an example: our once-upon-a-time sustainable fashion darling. The belle of the ball. The brand built a cult following over their infamous tagline “Being naked is the #1 most sustainable option. We’re #2.” The girls were gagged. “Ref girls” became an identity - flaunting their eco-conscious dresses and their moral superiority over fast fashion girls.
Then in 2019, Permira, a private equity firm, bought a majority stake in the brand. By 2023, customers were flooding Reddit and Instagram with complaints: cheap polyester replacing the signature sustainable fabrics, prices creeping higher, and label tags that now read “Made in Vietnam” instead of the brand’s proud “sustainably manufactured in LA” origin story. The Instagram comments section became a graveyard of “this isn’t the same brand anymore.”
Reformation wasn’t the only brand. So did dozens of other brands you used to love. And it’s not an accident. This is the private equity playbook, and once you see the pattern, you can’t unsee it.
When PE firms invest in a brand, they don’t just write a check and sit back. They’re working backwards from an exit in 3-5 years. They’re not asking “will customers still love this in 10 years?”, they’re asking “can we show enough growth to flip this?” And for them, more money = faster growth. They look for brands that already have momentum, inject capital, crank the levers to grow the brand into something sellable on paper to another strategic buyer, another PE firm or take public.
But the problem is that fashion doesn’t really work that way. It’s volatile. Brands take decades to build.
Cultural coolness isn’t linear, and it doesn’t respect five-year fund cycles.
And the data reflects that tension. PE-backed companies are estimated to be up to 10x more likely to go bankrupt than non-PE-owned peers. Roughly half end up in Chapter 11 or some form of financial distress. That doesn’t mean every deal fails. It does mean the model is structurally mismatched with an industry that runs on… and I hate to use this word but taste.
Fashion brands are being asked to grow at the pace of tech companies, even when the product and the customer simply can’t.
How cool brands become “boring”
Brands start feeling boring when private equity optimises for growth - stores open quickly. Product cycles tighten. Assortments widen.
What gets lost is the thing that made the brand matter in the first place. Creative decisions become safer. Risk starts to feel expensive. The brand stops surprising people.The brand just flattens.
The clothes are fine. The stores are busy. The numbers work. But the emotional pull weakens.
Most of the “boring” brand stories follow this pattern. Fashion punishes speed when it hasn’t earned scale yet. And once that cultural edge is gone, it’s very hard to buy back.
This is PE’s Dilution Playbook
#1: The Homogenisation Effect
When PE gets involved, brands start looking the same. Creative direction becomes safe. PE doesn’t want the brand taking risks on an avant-garde collection when it needs to hit aggressive revenue targets. You lean into what’s already working. And cool brands stop surprising. They start repeating themselves.
Mansur Gavriel is the clearest example. When GF Capital invested in 2019, the brand was already generating roughly $35 million in annual revenue, riding the success of its bucket bag, the “first post-recession It-bag.” Leadership shifted soon after, with the appointment of Isabelle Fevrier, whose background was at DFS Group, a global duty-free retailer owned by LVMH, a mass retail environment rather than a founder-led brand culture.
Over the next few years, the change was visible. The product began looking more generic, chasing trends rather than making them. It’s the classic PE fashion story: these firms see a brand on the rise and assume a cash injection will accelerate growth. But when a company is still founder-driven with a singular vision, growth is slower. A fashion brand typically needs to be north of $100 million in annual sales to stand on its own without its founder. Even then, it’s not easy to maintain. Today, nearly six years later, Mansur Gavriel’s revenue still appears to hover around $35 million. And the brand is still trying to find its footing, culturally speaking.
#2: The Brand Dilution
Overexpansion is where brand dilution begins. Once PE steps in, brands are often pushed to scale faster - stores open quickly, categories expand earlier than planned, and collaborations and frequent drops become a way to smooth near-term revenue. The result is sudden ubiquity - a brand that goes from being cool to being everywhere.
This is how brands end up with too many doors, too many SKUs, and not enough sell-through. Growth looks healthy on paper, but the consequence is brand dilution.
Ganni is often framed as a PE success story. Commercially, that’s hard to dispute. But culturally, the story is more nuanced.
When L Catterton acquired a 51% stake in late 2017,Ganni was generating roughly $40-45 million in annual revenue. It had strong cultural momentum with its influential It-girl following. The PE funding was to professionalise the business.
At the time, co-founder Nicolaj Reffstrup was explicit about restraint, “We do not expect to grow aggressively over the years. We are going to slow down slightly.” Wholesale had become too dominant. The long-term plan was to rebalance away from it. And in reality, the opposite happened.
Ganni expanded quickly from around 21 Nordic stores to more than 50 locations across Europe, the US, and Canada. Wholesale followed the same trajectory. Despite earlier plans to cut accounts, the brand grew to over 400 premium stockists across 20 countries. Wholesale came to represent roughly two-thirds of total sales.
Financially, the strategy delivered. Revenue reached €76 million by 2020, even in a pandemic year, and rose to around €160 million by 2022. Growth stayed in the double digits. Within five years, L Catterton was reportedly exploring an exit at valuations of up to $700 million.
But culturally, Ganni’s position shifted. As availability increased - more stores, broader wholesale - the brand’s edge softened; it was less insider.
Coolness eroded in a sense, because PE succeeded too much.
A similar pattern played out at Reformation.
In July 2019, Permira took a majority stake in Reformation, and from there, the brand’s strategy shifted. Scale was a priority. And in fashion, nothing kills coolness more than scale unfortunately. Stores opened fast. What was once a tight retail footprint jumped from around 14 locations in 2019 to roughly 61 by 2025.
Product cadence followed the same logic. Reformation started releasing 15–20 new styles every week - a pace that worked with growth, but sat awkwardly with a brand that built its identity on restraint. The clothes were still “Ref.” The messaging was still sustainability-first. But the feeling changed.
Like Ganni, Reformation shows how private equity can scale a fashion business quickly. It also shows how, under that pressure, what a brand actually optimises for can drift, even when the story it tells stays exactly the same.
#3: The Margin Optimisation
Under PE ownership, margin expansion is usually the fastest lever to pull. Revenue growth still matters, but it’s unpredictable. Costs aren’t. You can’t force customers to buy more, but you can make each unit cheaper to produce. And revenue growth still drives a large share of returns, roughly ~50–55% in many deal-level studies.
In fashion, that tends to show up in different ways. Suppliers change. Materials get swapped. Production moves offshore. On the rack, things don’t look dramatically different. But they’re cheaper to make.
At Reformation, that shift is measurable. In the four years following Permira’s investment, revenue roughly doubled, reaching about $300 million by 2023. The company has since signalled it is on track to exceed $500 million in annual sales. From a growth perspective, the strategy worked.
But the cost structure moved alongside that growth. Production that was once heavily Los Angeles–based shifted largely overseas; recent estimates put roughly 75% of manufacturing outside the US. Fabric composition changed as well. Materials that once leaned toward wool and silk increasingly gave way to viscose and polyester - including 100% synthetic pieces, even as price points stayed premium.
Emissions rose alongside growth, and external reporting showed an increase in absolute carbon output year-over-year - a predictable outcome of more stores and globalised supply chains.
Permira bought a brand with real demand and a sustainability story that justified premium pricing. That story does a lot of work. It protects margins. It gives consumers a reason to pay more without asking too many questions. Sustainability starts functioning more like brand equity. Something to maintain in the narrative, even as the underlying cost structure shifts elsewhere.
#4: The Debt Trap
Most PE fashion deals are structured as leveraged buyouts (LBO). The buyer puts up a relatively small slice of equity, sometimes as little as 10–20%, and finances the rest with debt. That debt is secured against the brand’s assets and future cash flows. And crucially, it lives on the company’s balance sheet, not the PE firm’s.
From day one, the business has to service it. Interest payments become a fixed annual obligation. Cash that might have gone into better product, stronger store experiences, digital infrastructure, or quality upgrades is instead diverted for lenders. The longer the fund holds the company, the more that pressure compounds.
This is also why timing matters so much. Most PE funds are working toward an exit around year five. Returns are expected. By that point, the business just needs to look sellable.
J.Crew is the clearest example of how this plays out in fashion.
In 2011, TPG Capital and Leonard Green & Partners acquired J.Crew in a LBO valued at roughly $3 billion. At the point of acquisition, the company was loaded with more than $1.5 billion in debt. Soon after, J.Crew was required to take on an additional $787 million in borrowing, much of it used to fund dividend payments back to the sponsors rather than reinvestment in the business.
Over the course of ownership, the PE firms extracted an estimated $765 million through management fees and debt-funded dividends. J.Crew, meanwhile, was left carrying a total debt burden of roughly $1.65–1.7 billion.
That leverage stripped the brand of flexibility at exactly the wrong time. As consumer tastes shifted toward casualwear and digitally native brands, J.Crew was boxed in by debt servicing.
By May 2020, J.Crew became the first major US national retailer to file for Chapter 11 bankruptcy during the pandemic.
The lesson here is that leverage changes what a brand can afford to do. When cash is already spoken for, creative risk narrows. Long-term brand building is forgone to give way to short-term survival.
When PE Has Been Successful
Brands tend to stay cool when PE enters late, after the brand identity is already locked in. When the founder or creative lead keeps control. When growth is paced. These are the exceptions, not the rule.
PE doesn’t always hollow brands out. In rare cases, it amplifies a vision that already exists. Moncler is one of the clearest examples.
In October 2008, The Carlyle Group acquired a 48% stake in Moncler. Instead of forcing a fast flip, Carlyle leaned into operational scaling that stayed consistent with luxury discipline. Expansion was selective. Distribution stayed tightly controlled. Growth prioritised D2C and flagship retail. Discounting and wholesale dilution were largely avoided.
In typical PE fashion - when Carlyle invested, Moncler operated roughly 6 mono-brand stores. By the time of Carlyle’s partial exit, that number had grown to 50+ globally, across key luxury markets in Europe, the US, and Asia.
Financial performance followed. Between 2008 and 2012, revenues reportedly increased by more than 200%. Sales rose from approximately €364 million in 2011 to around €780 million by 2015, with EBITDA expanding alongside revenue - driven by margin capture through owned retail rather than aggressive cost-cutting or quality erosion.
Carlyle exited gradually, selling down its stake ahead of and during Moncler’s 2013 IPO, and fully exiting by mid-2014. The IPO itself underscored the success of the strategy:
shares were 27x oversubscribed
the stock jumped 47% on its first day of trading
Moncler debuted with a valuation of over €4 billion, outperforming many luxury peers on entry multiples
Importantly, Moncler didn’t stagnate post-PE. In 2018, the brand launched Moncler Genius, rewiring the traditional fashion calendar. Instead of seasonal collections, Moncler invited designers like Simone Rocha, Craig Green, and later Pierpaolo Piccioli to reinterpret the brand through ongoing drops.
That same thinking carried into how Moncler showed up in the world. The Moncler Grenoble presentations evolved into headline events, blending high fashion with experiential spectacle. Shows were staged en plein air in rarefied mountain settings like Courchevel, St. Moritz, and most recently Aspen, where the Fall/Winter 2026 show unfolded against snowy peaks and rugged terrain.
Moncler also stayed tightly connected to the broader zeitgeist. Its “Warmer Together” Fall/Winter 2025 campaign starred Robert De Niro and Al Pacino, an unexpected pairing that extended the brand’s cultural reach well beyond fashion’s usual cast of faces. The signal is clear: Moncler is part of the cultural zeitgeist, and far from “boring.”
Moncler shows what happens when private equity enters after a brand’s identity is fully formed, leadership remains intact, and expansion follows luxury logic rather than financial urgency.
The second breakout case and one that’s still very much in motion is Khaite.
Khaite is useful precisely because it shows what PE can look like when creative control is preserved and growth is paced. After taking on a majority investment from growth equity firm Stripes in March 2023, founder Catherine Holstein has continued to lead the brand with a clear, intact point of view.
Importantly, Khaite wasn’t an early-stage rescue. The brand had already crossed $100 million in revenue by 2022, before Stripes invested.
Roughly two and a half years after Stripes’ reported ~$150 million investment for an 80% stake, Khaite began reporting double-digit growth across categories, including accessories, denim, knits, handbags, and footwear. That matters. It suggests Khaite’s appeal translated beyond fashion-insider buzz into repeatable commercial traction.
Operationally, the expansion has been measured. Their current plan is to open around one new store per year. As of now, Khaite operates five stores in the US and one in Korea.
What’s notable is where the capital seems to have gone. While many PE partnerships in fashion dilute creative identity through cost-cutting or material substitution, Khaite’s product has not visibly cheapened. Fabrication and price-value alignment appear consistent with earlier collections, and the brand’s design language hasn’t flattened into something more generic.
Holstein has stayed focused on the same product logic that built the brand: clothes and accessories that feel timeless and not trend-chasing.
Khaite sits in the narrow middle ground where private equity might work: creative leadership retained, disciplined retail expansion, quality maintenance and a brand identity that remains protected. The risk, as always, is time. The longer PE ownership stretches on, the more pressure builds.
For now, Khaite still feels special, still feels cool. The question is whether it can stay that way once scale is no longer optional.
🥀Thanks for reading! Let’s get to know eachother. Find me on Instagram, TikTok, or connect with me onLinkedIn!
this was so informative and interesting! ive always been very skeptical of private equity so really interesting to understand how it impacts creativity and design as well!! great essay 🤍