Lately, I’ve been revisiting older photos of myself and – there’s really no elegant way to put this – cringing. Hard. Fond remembrance and rose-tinted nostalgia be darned, what I’m feeling is full-bodied, gut-level recoil.
You see, it’s a uniquely modern millennial affliction to revisit one’s past selves in high-resolution – willingly, at that. And I get it, we’ve run out of trends to cycle through, and therefore, 2026 is the new 2016. Perhaps in my mind, the skintight, ripped skinnies tucked into bulbous brown boots combo did feel stylish too – it was, after all, Kate Moss who perfected the Gen-X boot-tuck.
Sadly, my 16-year-old self (far from the epitome of good taste that is Ms. Moss) was blithely oblivious to the retroactive embarrassment – nay, horror – his outfit choices would incite 10 years later. The (Instagram) archive remembers it all, even if we’d much rather forget.
But such, dear reader, is life.
Which is why a throwaway moment from Kendall Jenner’s recent home closet tour for Vogue felt uncomfortably closer to home than a Beverly Hills nepo-baby generally would. “I shot my house for Architectural Digest, like, six years ago, and they took a photo of this room,” she recalls, serenading us into the sweeping walk-in affair. “The photo haunts me to this day, I can’t stand looking at it,” she adds conspiratorially. Stars – they’re just like us, after all!
It’s this sliver of relatability – no matter how slight – that makes her all the more endearing to her fan base. Or shall we say, Kendall’s Kult?
The Kendall Show
Yet, for someone so intent on outgrowing her past, Kendall Jenner – currently in possession of 284 million followers on Instagram – has never been more watched. Which isn’t quite as many as younger sister Kylie’s or older sister Kim’s (390 million and 352 million respectively), but it’s still, well, a lot.
But then again, that’s hardly news.
Ever since the dawn of Keeping Up with the Kardashians (circa. 2007), and more centrally, after momager Kris signed her onto Wilhelmina Models at the tender age of 14, Kendall’s life has unfolded on national television like the E! Network equivalent of The Truman Show – only there’s no exit door.
We saw her book her first modeling gig for Forever 21, land her first cover shoot with American Cheerleader magazine, walk her first high-fashion show with Marc Jacobs, and earn Forbes’ title of the “world’s highest paid supermodel”, all while claiming that her reality TV fame hindered her career.
She also once walked out of a runway training session because she was “bored”.
And of course, aside from her Instagirl ascension (In a Vogue profile, she says, “You don’t want to do too many posts… You want to leave them wanting to come back.”), her Karl Lagerfeld kosign, and her konfounding kommitment to slip-on sneakers (and flats in general), she also owns the massively successful 818 Tequila brand, co-owns the klothing line Kendall+Kylie, and serves as the Creative Director of FWRD.
“I’ve been raised to be a businesswoman,” she says, and that means, unlike the Kardashian caveat of total visibility, Kendall created her own mythmaking.
Keeping Up With Kendall
Okay enough with all the K’s, let’s talk Kellys. Specifically, that bordeaux boxcalf Kelly from Kendall’s rotation in the Vogue video. “They’re super worn, these Kellys,” she chimes, “And the leather is super crunchy, and I love when the leather cracks and there are scratches, and there’s scuffs, and the corners are all messed up. Like, this is so chic to me and so beautiful.”
She also goes on to flaunt a giant Veau Doblis suede Birkin (“My dream”) and a limited-edition JPG Shoulder Birkin; “Any Hermès bags that I own, I’m very particular about the ones that I have,” she explains. “I love really old ones.”
And if you happen to be anywhere as remotely online as yours truly, you’ve also, no doubt, witnessed the barrage of The Row bags that populate the pop-culturista’s closet, a tiny Prada bag momager Kris got for baby Kendall (“Nothing fits in this, actually, to answer your question”) and a one-of-a-kind floral LV Keepall gifted to her by the late Virgil Abloh himself.

What’s also noteworthy, however, is truly just how much Kendall’s style has evolved since the 360-degree video tour of her closet from a decade ago. “It’s very colorful in the last thing, and there should be a side-by-side because it’s not as colorful anymore – and a lot more organized,” she says.
Because now, Kendall has truly grown into her own.
Gone are the metallics and thigh-high orange boots she hobbles around in, the Louis Vuitton fanny-packs of questionable authenticity, and the bright, bold blue and yellow Hermès that her Calabasas clan would approve of.

Instead, as she says herself, “When it comes to style within my family, at least, I have different style choices than some of them. Sometimes I’ll definitely walk into a family dinner, and one or two of them will be like, ‘This is cool, what is this?’ A little side-eye action.” And as her (old) Céline Nano Luggage can attest, “When I love something, I love something.”
Really, isn’t that all we want from our style-stars these days? An unwavering commitment to their own, unique sense of personal style?
Age vs. The Illusion of Age
But really, what perhaps brings the tension around Kendall’s aesthetic to a head – and in the process, constitutes the crux of the obsession around Kendall Jenner – is not the closet reveal for Vogue, but the Architectural Digest tour of her Wyoming mountain home that dropped last December. Or more specifically, the discourse around it; the tension here being the idea that you can look, as hackneyed as it is, old money, without actually being old money.

Now, for some context, the credit for this goes to Heidi Caillier – advocate of “grandma chic” in interior design – and the house reflects her colorfully quirky, yet restrained, maximalism, whose vintage (or vintage-inspired), one-of-a-kind pieces are a stark departure from the Kardashians’ other famously minimal residences with their tastefully beige bathroom-counters.
And there’s one camp (or shall we say, kamp?) that finds this everyday maximalism entirely consistent with Kendall’s personal style – which generally consists of straight leg pants, simple tanks and tees, and classic black loafers, paired with playful, unexpected layering, scandalously-cinched archival skirtsuits, well-worn jackets, and, of course, rare vintage purses.
Then there’s the other camp – the skeptics.

They look at the exact same house and see… cosplay. “In Kendall’s house,” writes interior designer Patricia Rodi, “you feel that compression of time.” You can reference it, you can approximate it, you can moodboard it into oblivion, but you simply can’t manufacture lineage. Kendall’s look – and by extension, house- feels performative (at times) because her trappings and trajectory do not have the stealth wealth element to it; it feels cultivated, artificial. As Rodi writes, “There’s no awkward middle phase, no visible evolution, no sense that things have been edited or replaced over years.”
Thus, she claims, in many ways, Kendall’s kult represents this very American fixation with age, or the appearance of age. ‘Old’ signals legitimacy. Cultural depth. It suggests lineage, taste, and a life lived slowly, and it’s hard to tell whether Jenner’s vintage, patinated Kelly is truly something she plans to wear time and time again, or she’s only in on the trend because it is on-trend.
After all, she did say, “I could have done a lot of things, but I chose to be this baby businesswoman.” The question is, are you buying what she’s selling?










It’s more performative than personal style.
She’s trash just like the rest of her family.
#kartrashians
That’s just mean and harsh. None of them, and especially Kendall are trash.
Maybe not trash. but trashy for sure.
Period
It’s a style I enjoy and appreciate, unlike that of the rest of the clan, be it performative or authentic.
All style is to a degree performative, imo. We all try to tell a story when we dress to leave the house. Very rarely is the story we tell about ourselves 100% true.
she looks good because she’s a tall slim woman with the body most clothes are made for but beyond that it’s pretty uninspired basic white rich girl style circa 2020s.
I find Kendall to be the most annoying and kontrived of her family though so I’m biased. I’m not a fan of her sisters either but someone like Kim who unambiguously lives for the spotlight and dresses accordingly is a lot more bearable to me than a Kendall or Sophia Richie type who pretends to hate the attention.
Another beautiful and thoughtful article, Sajid. Well done!
Who is we? Kendull is lucky she is skinny, has stylists and money. Very boring. She only looks good abroad.
Noting that Kendall(TM) is a product of stylists and other decor professionals is not anti-age/legitimacy. The looks/style are simply not organic. Or is this something Gen Z was trained not to discern? A rare miss from this columnist.
A lot of Gen Z just doesn’t care, authenticity isn’t even a question to them because everything they’re seeing is staged for social media
Now I’m bored.
Isn’t that the whole thing about the Kardashian/Jenner clan? Nothing about what they do is original.
Kendall’s style appeals to me, it is much like my own, her style is certainly very different than the over the top boobs out style that many in her family seem to favor.
sigh im the problem. im commenting on a kendull post but i do think she’s the one w/ style that’s most similar to mine (if i had that kind of money) BUT i actually find her the most unlikeable kardashian. her 818 sits unsold in my local liquor store and they actually dropped the price from $80 CAD or so to $60 CAD or so.
Sajid, always love your takes. Thanks for this one.
Someday I’d love to hear your take on the new batch of premium offerings (Strathberry, Songmont, Polene, Aest) and other niche and indie brands. As well as trends in the handbag space that aren’t tied to celebs. Thank you!