As co-founder of Who What Wear and host of the Second Life podcast, Kerr has spent two decades reshaping how audiences engage with fashion journalism. Her current Substack newsletter (Hi Everyone with Hillary Kerr) blends wardrobe strategy with career insights for 250k+ subscribers.
Hillary Kerr’s career exemplifies the evolution of modern fashion journalism into a multi-platform storytelling enterprise. Beginning in the early 2000s at ELLE magazine’s New York features desk, she honed her editorial voice through celebrity profiles and trend analysis before co-founding Who What Wear in 2006. This digital-native publication disrupted traditional fashion media by blending street style photography with e-commerce strategy, ultimately expanding into a global brand with Target collaborations and international editions.
"My pivot from print journalism to digital entrepreneurship felt like jumping without a parachute – terrifying, exhilarating, and ultimately the best decision I never planned."
This masterclass in practical luxury demonstrates Kerr’s ability to translate two decades of fashion expertise into actionable advice. Through meticulous outfit breakdowns featuring Tibi skirts and Jamie Haller heels, she reveals her "three-places/three-outfits" philosophy for business travel. The article’s impact lies in its rejection of disposable fast fashion, instead advocating for strategic investment pieces – a stance that generated 1,200+ reader comments debating capsule wardrobe principles.
Blending product recommendations with cultural commentary, this piece confronts fashion’s body positivity paradox. Kerr’s analysis of reader feedback ("Your choices are unflattering and too expensive") becomes a springboard to discuss size-inclusive styling and value-per-wear calculations. The $55 Madewell trousers recommendation sparked a 300% inventory sellout within 72 hours, illustrating her direct market influence.
This evergreen guide to corporate fashion distilled Kerr’s "polished practicality" ethos into actionable rules. Her advocacy for J.Crew belts as power accessories and rejection of "stiff suiting" helped redefine business casual for the hybrid work era. The article remains Who What Wear’s most-shared workplace style piece, with 850k+ Pinterest saves.
Kerr prioritizes products demonstrating measurable wearability – pitch denim brands with third-party durability testing or accessories companies tracking customer reuse rates. Her 2025 trouser analysis compared 29 pairs’ cost-per-wear metrics, setting a precedent for empirical fashion journalism.
With 200+ Second Life podcast episodes profiling career pivots, Kerr seeks brands built through unconventional paths. Successful pitches often include founder interviews addressing failure points – like the Jamie Haller CEO discussing early manufacturing disasters.
Her integration of Substack newsletters with Instagram reels and podcast episodes creates opportunities for multi-format storytelling. A recent successful pitch involved a 4-part series on sustainable wool production across written, audio, and video formats.
Kerr’s "investment dressing" philosophy favors products designed for 5+ years of use. Pitches for seasonal collections are less successful than those emphasizing timeless construction – note her recurring coverage of Khaite’s decade-old denim jacket design.
With 72% of her Substack content featuring exclusive previews, Kerr values early access to design processes. Successful pitches often include studio walkthroughs or pre-launch interviews with creative directors.
At PressContact, we aim to help you discover the most relevant journalists for your PR efforts. If you're looking to pitch to more journalists who write on Fashion, here are some other real estate journalist profiles you may find relevant:
