J.Crew Quietly Uses AI, AI-Powered Personalisation Comes to Kenneth Cole, AI Dressed Me (and It Worked)

J.Crew quietly experiments with AI-generated nostalgia

J.Crew has been caught dipping into the uncanny valley, using generative AI to create faux-vintage catalogue imagery that mimics its iconic 1980s-90s aesthetic. The images, styled to evoke its aspirational preppy past, were revealed by Blackbird Spyplane to be AI-generated artworks by “AI photographer” Sam Finn, though neither J.Crew’s original posts nor captions disclosed their synthetic origins. Subtle visual glitches gave the game away: warped limbs, inconsistent shadows, and nautical setups that made no sense. The campaign even nodded to iconic creatives like Bill Cunningham, but in doing so, ended up replacing real artistry with algorithmic facsimile.

Why it matters: This case raises bigger questions about authenticity, transparency, and the limits of nostalgia marketing. J.Crew’s attempt to evoke its legacy via AI-generated imagery ironically undermines the very human craftsmanship and cultural cachet that made its original catalogs aspirational.

J.Crew used A.I. to counterfeit their own vibes

Why? An Exclusive Spyplane Investigation

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Kenneth Cole Deploys Selectika AI

Kenneth Cole Productions has integrated Selectika’s visual AI recommendation technology into its e-commerce platform, aiming to personalize the online shopping experience and improve product discovery. The tool analyzes shopper preferences to serve relevant suggestions across the brand’s catalogue. Selectika says the partnership brings Kenneth Cole’s long-standing spirit of innovation into the digital age, helping boost engagement and ease of navigation for online customers.

Why it matters: As fashion brands compete on experience, not just product, AI-powered recommendation engines are becoming a must-have. For heritage labels like Kenneth Cole, this move is about staying relevant and converting browsers into buyers.

New Collaboration!! 📌 We are proud to team up with the one and only Kenneth Cole Productions — a brand with a rich history of pushing boundaries in both fashion and social advocacy. Kenneth Cole’s… | Selectika AI

New Collaboration!! 📌 We are proud to team up with the one and only Kenneth Cole Productions — a brand with a rich history of pushing boundaries in both fashion and social advocacy. Kenneth Cole’s journey began with a bold move: selling shoes from a trailer parked on the streets of New York City. With our visual AI recommendation technology, we’re bringing that same spirit of innovation to their online store. It will help customers navigate vast catalogues by offering personal and relevant recommendations—boosting engagement and making it easier to discover what they love! 👏 A sincere thank-you to the talented people who led this initiative: on Kenneth Cole’s side, Mashbir - משביר and Girit Interactive on our side, Moshe Harush and Nuphar Gabrieli and the Selectika AI team for their dedicated efforts. If you’re ready to create more value for your customers, talk to us! 📩 hello@selectika.com

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AI Dressed Me (and It Worked)

Stylist editor Felicity Thistlethwaite tested Google’s Gemini Live as a personal stylist, and was surprised to find it nailed her wardrobe choices. Initially skeptical about AI's place in her personal life, she ended up using the tool to identify plants, check her car oil, and ultimately assemble a complete outfit, down to shoes and jacket, with smart, context-aware recommendations.

Why it matters: For fashion retailers, this signals a growing appetite for AI-assisted shopping tools that go beyond generic suggestions to offer real-time, hyper-personalized styling support, especially for time-strapped consumers juggling busy lives.

What happens when you let AI style you (clue: compliments come thick and fast)

As a time-poor shopper, it worked a treat.