The 10 Best Books on Cities and Urban Life (That I Actually Recommend)
If you’ve ever wondered why some streets sing and others snore, these ten books will jolt your urban imagination awake. No polite city-planning manuals here—just sharp takes, sly humour, and a love of the messy metropolis.
Messy Cities: Why We Can’t Plan Everything edited by Dylan Reid, Zahra Ebrahim, Leslie Woo and John Lorinc – Fresh off the press, this book revels in grit and glitch. It argues that friction—noise, diversity, surprise—isn’t a flaw but the beating heart of urban life. Messes can be an asset. Even my kid likes this book (high praise).
Invisible Cities by Italo Calvino – A dreamscape of invented metropolises (all different facets of Venice) described by Marco Polo to Kublai Khan. Proof that the best city guides sometimes contain zero maps and 100 percent poetry.
Triumph of the City: How Our Greatest Invention Makes Us Richer, Smarter, Greener, Healthier, and Happier by Edward Glaeser – An economist’s love letter to density. Glaeser insists (he’s convincing!) that cities make us better (and more environmentally responsible) in every way.
The Power Broker by Robert Caro – 1,300 pages on Robert Moses’s empire-building and power accumulation in New York City. Worth every wrist-cramping minute for its X-ray look at the dark side of public service and urban planning, and how it can build and destroy.
The Death and Life of Great American Cities by Jane Jacobs – The ultimate urban mic-drop. Jacobs champions sidewalks, small blocks, and nosy neighbours. She’s an avid critic of urban planners—and in turn, planners love her. Her influence is everywhere—especially on public hearing night.
Flâneuse: Women Walk the City in Paris, New York, Tokyo, Venice and London by Lauren Elkin – A feminist stroll through cities on her own terms. Think flâneur, but with literary druthers, excellent shoes and better tastes.
Happy City: Transforming Our Lives Through Urban Design by Charles Montgomery – Argues that bike lanes and park benches are basically happiness machines. I had a mentor that carried a dog-eared copy of this book throughout Europe. Now he’s the editor in chief of an urban mag.
Cities for People by Jan Gehl – A manifesto for designing places where humans, not cars, come first. Gehl led the charge in Copenhagen and the world followed suit. Radical in its common sense.
On Looking: A Walker’s Guide to the Art of Observation by Alexandra Horowitz – A dozen walks with experts on a range of subjects that teach you to notice all the signs, smells, and sidewalk quirks you’ve been missing all along.
The Flâneur: A Stroll Through the Paradoxes of Paris by Edmund White – Louche, literary wanderings through Paris. Less self-help, more self-indulgence—exactly as it should be.
Pack these in your tote bag and prepare to roam, rethink, and maybe miss your bus stop. Sure, you might need a full-on baby carrier to lug around the 1,300 page book, The Power Broker—but it’s worth it.
