Ian Connor recently confirmed his latest gig styling Kylie Jenner. We examine the impact this move may have on streetwear culture at large.

Celebrities, socialites and other high profile individuals almost always hire a stylist. It’s such a common practice that most of us expect it without so much as batting an eyelash. However, every once in a while, an unlikely stylist-client relationship occurs, leaving the rest of the world scratching their heads in confusion and wondering how it happened and what it means.

For instance, last week the social media world met “Gosha Kylie,” after which the pre-pubescent innanets went slightly bonkers. The youngest K of the infamous alliteration-favoring brood posted an Instagram picture in which she sported what was quickly identified as the “All Over” tee from Moscow-based Gosha Rubchinskiy’s Fall/Winter 2015 collection. The day before her big alter ego reveal another one of the Internet’s favorite love-to-hate personality’s (enter stage left, Ian Connor) took to the ‘Gram to share a picture of Jenner wearing a fairly rare Supreme T-shirt that has since been linked to a 2010 Rizzoli x Supreme book release. Connor captioned the photo, “And Tonight We Shift Cultures Thank You.”

And Tonight We Shift Cultures Thank You.

A photo posted by Ian Connor (@ianconnorsrevenge) on

A week prior, on September 12, Connor tweeted, “Got the Kylie Jenner styling job,” leading to speculation that the younger Jenner’s sudden streetwear transformation was masterminded by the Skechers-wearing, petit-statured, A$AP Mob protégé.

If Connor is indeed Kylie’s new stylist what does that mean for the niche brands he’ll surely be outfitting her in? If you’re an alarmist, you might anticipate a bevy of green-haired, pointy-nailed Jenner disciples flooding into boutiques they’ve previously never heard of and asking for the same shirt their leader wore. After all, the Kardashian’s have proven their selling ability through their seemingly endless amount of business ventures. Yet even still, much of this ability rests on projecting a lifestyle and aspirational sensibility that resonates with their core fan base. Thus far, their core fan base has certainly not been the hyper-dedicated streetwear crowd.

Perhaps that could be the reason Jenner even hired Connor to style her. She is the youngest in a family that includes an older sister who has become a sought-after fashion model. It may simply come down to the littlest Jenner wanting to be recognized as her own separate entity. What better way to do that than by aligning yourself with the edgy personalities and cult-level cool of streetwear brands?

And although Connor has quite often ended up as the internet’s favorite punching bag, it’s also hard to deny that his track record is very near flawless; when he anoints something as the next cool thing it almost always becomes just that. Despite his youth, and despite often posturing as an idiot savant-meets-flâneur personality sprinkled with a dash of laissez-faire – something that often leaves the internet questioning what it is he actually does – Connor has proven to have a near encyclopedic knowledge of the fashion landscape, and a fairly mature eye where styling is concerned.

Perhaps the most ready parallel of what Connor’s relationship with Jenner may offer is that of Kanye West and Kim Kardashian. When West, who has a similarly polarizing persona, began dating Kim Kardashian it was reported that he also became her unofficial stylist. There was even an episode of the family’s scripted reality show in which Kanye asks Kim get rid of her existing wardrobe so that he can help her start afresh. As a result, many believed that it was West who initiated Kardashian’s sartorial transformation. For his part, West had already shown a collection at Paris Fashion Week and was actively attempting to make inroads in high fashion. In the era of being Mrs. Kardashian-West, Kim has covered Vogue, CR Fashion Book, published a book of selfies, attended the Met Gala, and secured countless other fashion magazine covers. A few years ago, many sniped that those things would never happen—especially the Met Gala. The latter stemmed from a prevalent rumor that suggested while West was in good standing with Anna Wintour, Kardashian had somehow run afoul of the rarely-smiling power player.

Yet despite the success of the Kanye-Kim model, it’s difficult to say whether Connor working with Jenner will legitimize her in a similar fashion. Followers of streetwear are a very different beast than the often novelty-obsessed high-fashion acolytes. It will take more than wearing the right clothes and being photographed in the right places for Jenner to truly make an impact. Dedicated collectors and (sometimes) near-rabid Stans associated with streetwear culture aren’t looking for the next it-girl.

James Jebbia: Supreme



Buy at END.

Instead, value is placed on knowledge of the product, an understanding of product history, and in many ways, exclusivity. It’s a different type of exclusivity than that associated with a storied fashion house. Where many high-end designers see their exclusivity anchored to a sense of elitism, and to an extent social stratification, streetwear’s elitism often appears to be knowledge-based. With streetwear, a product isn’t special purely because only a small fraction of people can afford it; it’s special because of the pain of acquisition. Remaining in the loop about limited-edition pieces and new drops comes largely from being plugged into a community of like-minded people, and knowing where to look or who to ask.  The Rizzoli x Supreme shirt mentioned earlier is a good example. In theory, it’s a T-shirt. Yet the fact that it’s the limited product of an OG streetwear brand elevates its worth.

Evidence of this mentality can even be found in Highsnobiety’s very own comment sections.  At any time of the day you’ll see a number of disgruntled loyalists railing about who should and shouldn’t be wearing what, all on the basis of perceived level of Hypebeast-ness.

Gosha Kylie

A photo posted by King Kylie (@kyliejenner) on

Conversely, one has to wonder what Connor hopes to achieve by styling Jenner. It’s certainly a dramatic departure from clients like Wiz Khalifa, whom Conner implied was less than willing to give him full creative control. It could simply be that Connor views Jenner as a blank slate for experimentation. For one, she does not have a history of wearing the brands he’s intimately familiar with. She also has an incredibly high level of exposure and comes from a family (minus Kanye and sometimes Khloe) who has previously displayed no inclination towards Connor’s style preferences. Revamping Jenner’s image would certainly be an undertaking. It could also be a simple as a means to an end: Connor lends his stamp of legitimacy to Jenner in his world, and she does the same for him in hers. Call it a trade-off of cool points if you will.

All-Over Print T-Shirt

All-Over Print T-Shirt


Gosha Rubchinskiy

Buy at ssense

Whatever happens, it seems pretty doubtful Jenner will end up being the harbinger of doom for brands like Gosha Rubchinskiy, Supreme or whatever else Connor may suggest she wear. She’s not the first celebrity to bring what others perceive as a sub-culture to the mainstream, and she certainly won’t be the last. While she may expose these labels to larger audiences, it’s unlikely that she’s capable of single-handedly diluting an entire lifestyle. Certainly, the culture surrounding streetwear is part of what makes it unique, and culture is a far more difficult thing to influence than individual people.

In short, while Connor and Jenner may seem like strange bed fellows, at this point, it’s hardly a pairing worth overthinking. Though it might be interesting to keep an eye on how Connor will choose to style Jenner as his past client list seems to have been predominately male.

Words by Stephanie Smith-Strickland