AI in the Closet: Sartre, Taylor, Heidegger on Style
Ralph Lauren launched Ask Ralph, an AI co-stylist built with Microsoft/OpenAI, today. More than a business move, it signals a philosophical inflection point. Dressing declares identity; each outfit projects who we are. With AI as co-stylist, the question becomes: does it shrink our freedom or expand it? In what follows, I’ll consider AI styling through three philosophical lenses: Sartre’s existential freedom, Taylor’s dialogical self, and Heidegger’s account of technology as both danger and revelation. Along the way, I’ll situate Alta, lookingGLASS, Daydream, Stitch Fix, and Vivrelle’s recently launched Ella AI (some hot emerging startups) within this frame.
For Sartre, authentic existence requires owning our choices. This puts AI styling in a philosophical bind: does algorithmic guidance expand our freedom or undermine it? Clothing has always been a particularly vivid form of this freedom: each outfit is a small self-portrait in fabric. The risk of AI stylists, from a Sartrean lens, is “bad faith,” the temptation to let algorithms decide for us, to hide behind recommendations instead of owning our freedom. If we blindly accept Ask Ralph’s suggestions, we risk becoming passive wearers rather than active creators of self. Still, Sartre’s framework also reveals AI’s promise. Used deliberately, AI recommendations are not constraints but provocations. Startups like Alta and lookingGLASS, which remix a user’s existing wardrobe into fresh combinations, actually expand freedom. They show us selves we might not have imagined, the forgotten blazer, the unlikely color pairing. Rather than eroding agency, these systems offer new material for existential play.
Taylor reminds us that identity formation is always conversational. We’ve always dressed in dialogue with others—peers, magazines, subcultures, icons. AI just introduces a new conversation partner. Ask Ralph converses with Ralph Lauren’s archive, letting users situate themselves in decades of design codes. Daydream, the chat-based shopping agent spanning 8,000 brands, opens dialogue with the entire fashion marketplace. Stitch Fix’s hybrid of AI assistant and human stylist reminds us that dialogue is richer when technology and human empathy work together. The question for Taylor is not whether dialogue with algorithms is authentic, but whether it is meaningful. If the interaction helps us articulate a sense of self, then AI stylists are not replacing dialogue. They extend its range. Vivrelle’s Ella AI, launched last week, complicates this dialogue by situating styling in the luxury rental economy. Here, taste and identity are less about ownership and more about circulation, raising questions about authenticity and selfhood in shared style.
Heidegger's concept of enframing, technology's tendency to reduce everything to manageable resources, captures the risk of AI styling. We might begin seeing our wardrobes not as sites of self-expression but as datasets to be optimizedWe risk seeing closets not as sites of self-expression, but as inventories to be managed. But Heidegger also saw that technology reveals. In its reduction, it can disclose new possibilities. AI stylists reveal hidden patterns in our clothes, latent styles in our history, and unexpected resonances between heritage and trend. lookingGLASS reveals the overlooked value in what we already own; Ask Ralph reveals connections across fifty years of Polo design. Even the massive dataset approach of Daydream reveals something: a global field of aesthetic possibility that exceeds any one person’s imagination.
On the business side, AI fashion styling is accelerating fast. Here’s what’s hot in AI fashion styling right now 👇
🔥 Alta – $11M seed (Menlo Ventures, Karlie Kloss, Tony Xu). Generative wardrobe curation + avatars, pilot programs with CFDA/LVMH.
🔥 lookingGLASS – Backed by Accenture Ventures. AI “remix” tools that get more from what’s already in your closet, emphasizing sustainability.
🔥 Daydream – ~$50M seed. Ex-Stitch Fix COO Julie Bornstein’s agentic AI shopping assistant spanning 8,000+ brands.
🔥 Stitch Fix – The OG: hybrid human + AI model, still a reference point for the industry.
🔥 Vivrelle’s Ella AI – Launched Sept 2025 (last week) with $19M. Blending rental, resale, and retail to reshape luxury “ownership.”
And Ralph Lauren itself? FY2025 revenue hit $7.08B (+6.7% YoY), net income climbed 15%, and the brand amplified its cultural relevance at the US Open with a 20th-anniversary collection and recycled-material uniforms. Ask Ralph fits squarely into this playbook: heritage + digital transformation + cultural influence.
AI stylists are set to transform how we shop, how brands sell, and how identity itself gets expressed. Don’t sleep on it.
Sources for Ask Ralph, Ralph Lauren Financials, and US Open:
Ralph Lauren launches Ask Ralph (AI stylist, Microsoft partnership, heritage/digital strategy):
Hypebeast, “Ralph Lauren Introduces ‘Ask Ralph’ AI Stylist Bot” (2025-09-08)
Ralph Lauren Corporate, “Ask Ralph, a New Conversational AI Shopping Experience” (2025-09-08)
ABC News, “Ask Ralph is the new AI stylist tool for Ralph Lauren shoppers” (2025-09-08)
Microsoft Blog, “Ask Ralph: Where style meets AI—a new era of conversational commerce” (2025-09-09)
Wall Street Journal, “Ralph Lauren Has Entered the AI Age” (2025-09-09)
Good Morning America, “Ask Ralph is the new AI stylist tool for Ralph Lauren shoppers” (2025-09-08)
Yahoo Finance, “Ralph Lauren Full Year 2025 Earnings: In Line With Expectations” (2025-05-24)
Ralph Lauren Corporate, “First Quarter Fiscal 2026 Results Exceeding Expectations” (2025-08-06)
Public.com, “Ralph Lauren (RL) Earnings: Latest Report, Earnings Call & Financials” (2025-08-06)
Observer, “Ralph Lauren Debuts 2025 U.S. Open Collection” (2025-08-05)
Sources for Startup Funding/Business
Alta ($11M seed, Menlo Ventures, Karlie Kloss, Tony Xu, LVMH/CFDA pilots):
TechCrunch, “Alta raises $11M to bring 'Clueless' fashion tech to life with all-star investors” (2025-06-15)
The AI Insider, “Fashion AI Company Alta Closes $11M Round” (2025-06-16)
TechNews180, “Alta Secures $11M to Launch AI Stylist for Your Wardrobe” (2025-06-15)
lookingGLASS (Accenture Ventures, wardrobe remix AI, circular focus):
Accenture Newsroom Blog, “Accenture invests in Looking Glass” (2023-02-06)
Yahoo Finance, “lookingGLASS Launches Monthly Subscription to Support Millennial ...” (2024-06-03)
Daydream (~$50M seed, Julie Bornstein, chat-based, 8,000+ brands):
Forbes, “Julie Bornstein's Daydream Is Redefining AI Fashion Shopping” (2025-06-25)
Vogue, “Is Daydream’s AI Platform the Answer to Fashion’s Discovery Problem?” (2025-06-25)
TechCrunch, “Julie Bornstein’s Daydream is releasing an AI-powered chatbot for fashion-related shopping” (2025-06-25)
Vivrelle/Ella AI ($19M round, rental+retail AI, Sept 2025 launch):
Fits App Blog, “Best AI Stylists in 2025 – Top 5 free & paid services” (2024-12-31)
