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Messy Cities
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03 June 2025

Can messiness make our cities more liveable, lively, and inclusive?
Crowded streets, sidewalk vendors, jumbled architecture, constant clamour, graffitied walls, parks gone wild: are these signs of a poorly managed city or indicators of urban vitality?
Messy Cities: Why We Can’t Plan Everything argues that spontaneity and urban workarounds are not liabilities but essential elements in all thriving cities.
Forty-three essays by a range of writers from around the world illuminate the role of messy urbanism in enabling creativity, enterprise, and grassroots initiatives to flourish within dense modern cities.
With pieces on guerrilla beaches, desire lines, urban interruptions, and the inner lives of unlovely buildings written by experts from all walks of life, Messy Cities makes the case for embracing disorder while not shying away from confronting its challenges.
One of Canadian Architect's 'Best books for Canadian architects: 2025'
One of Bloomberg Cities Network's 'Summer Reads for Urban Innovators'
"Messy Cities highlights the richness and clues in community-led design, and how the scrappiness of cities and urban diversity are what make these areas strong, vibrant, and livable." – Brittany Andrew-Amofah, Perspectives Journal
"This book ... focuses mostly on personal, organic, on-the-ground descriptions of the ways neighbourhoods work in Toronto: How one created a “gorgeous landlocked oasis” out of a vacant lot at the start of the COVID‐19 pandemic. The veggie grannies of West Chinatown. The banquet halls, primarily serving the South Asian community but not exclusively, that have become important cultural conduits even though they’re usually bland buildings in the middle of suburban industrial areas." – Frances Bula, Literary Review of Canada
"Messy Cities doubles as a love letter to Toronto’s growing immigrant neighborhoods, and an archive of the everyday strategies by which communities make an often hostile city work for them." – Sabina Sethi Unni, Places Journal
"[S]tudents of urbanism looking for an alternative to the straight and narrow path will find much to consider." – Publishers Weekly
"Cities will always grapple with disorder and the best ways to manage it. But one core message embedded in this collection of 43 essays is that it can be helpful for residents and local leaders alike to consider when that “mess,” whether a glut of street vendors or a complicated traffic intersection, is actually an asset." – Bloomberg Cities Network, '5 Summer Reads for Urban Innovators'
"This anthology of (mostly) brief essays celebrates what’s now known as “messy urbanism” – the serendipitous, unplanned ways people shape urban environments, from graffiti to street vending. Appropriately polyphonic, its diverse contributors include urban planners, artists, physicians and geographers." – Emily Donalson, Globe and Mail
"With examples from Toronto and around the world (Mexico City, Cape Town, Los Angeles, Tokyo and points beyond), it’s a book that takes an intentionally scattered – one could say messy –approach to considering the value and the complications of spontaneous and unplanned city building." – Edward Keenan, The Toronto Star
Zahra Ebrahim is an urbanist, educator, and strategist. Her award-winning work focuses on building bridges between institutions and their public, working with communities to co-design towards better social outcomes and leading some of Canada’s most ambitious participatory infrastructure and policy programs. She currently co-leads Monumental, a national organization focused on projects that advance fair, just, and culturally competent citybuilding, with previous experience leading organizations across multiple sectors. She is currently an Adjunct Professor at the Daniels School of Architecture and Urbanist-in-Residence at the University of Toronto’s School of Cities. She currently lives in Toronto with her partner, and their whippet, Zada.
John Lorinc is a journalist and editor. He reports on urban affairs, politics, business, technology, and local history for a range of media, including The Globe and Mail, Toronto Star, Corporate Knights and Spacing, where he is senior editor. John is the author of five books, including No Jews Live Here: A Memoir (Coach House Books, 2024), and has co-edited eight anthologies for Coach House, including The Ward (2015), Any Other Way (2017), and Messy Cities (2025). John is the recipient of the 2019/2020 Atkinson Fellowship in Public Policy and was the winner of the Writers' Trust Balsillie Prize for Public Policy, for Dream States: Smart Cities, Technology and the Pursuit of Urban Utopias (2022). He lives in Toronto.
Dylan Reid is a co-founder and now the executive editor of Spacing magazine, an award-winning print quarterly about Toronto urbanism and public space that recently celebrated its 20th anniversary. He is the author of the Toronto Public Etiquette Guide and co-editor of other books about Toronto. He was co-chair of the city government’s Toronto Pedestrian Committee and later co-founder of the advocacy group Walk Toronto. He is also a fellow at the Centre for Renaissance and Reformation Studies at the University of Toronto, and author of several scholarly articles about the history of cities in Renaissance France.
Leslie Woo is a dynamic tri-sector athlete known for her expertise in uniting public, private, and not-for-profit leaders to co-create innovative urban policy solutions. With over 30 years of experience as an urban planner, architect, and community activator, she has been central to shaping urban development in Canada’s largest metropolis. Leslie serves on the boards of Waterfront Toronto and the Yee Hong Centre for Geriatric Care and is a trustee of the Urban Land Institute. A Senior Fellow at the University of Toronto’s Munk School of Global Affairs and Public Policy, Leslie champions women city builders on her blog.
Contents & Contributors
Introduction – Dylan Reid
Dixie Road – Fadi Masoud
These Walls, These Roads – Ameer Idreis
Designing out Disorder – Cara Chellew
From Loud to Lively – Leslie Woo
Mexico City's Jumbled Apartment Buildings – Daniel Gordon
Flexible Streets – Dylan Reid
Satisfying Our Thirst for Agency – Colin Ellard
The Collective Effervence of Messy Parks – Jake Tobin Garrett
Industrial Land's Secret Sauce – Karen Chapple
A Food Map of Toronto – Karon Lui
A Beach Like No Other – Shari Kasman
Sports and Spaces – Perry King
Leave the Leaves – Lorraine Johnson
Interruptions – Zahra Ebrahim
The Readable City – Shawn Micallef
Beyond the Lawn: Meadow or Mess? – Nina-Marie Lister
Planning for an Unplanned City – Jason Thorne
A Farewell to El Gran Burritov – John Kamp and James Rojas
Banquet Halls and Belonging – Sneha Mandhan
Tokyo: The Quintessentially Messy City? – Andre Sorensen
The Ballet of the Parking Lot – Brendan Stewart and Daniel Rotsztain
We Can Live With That – Leslie Woo
Tower Communities Are What We Make Them – Ajeev Bhatia
The Case Against Controlling Infrastructure – Andrés Borthagaray
An Argument Worth Having – Chiyi Tam
Everything is Everything But The Details Matter – Alexandra Lambropoulos and Sami Ferwati
Hidden Struggles – Eileen De Villa
Cities for Women and Girls – Elsa Marie D'Silva
Non-humans (Heard and Unheard) – Suzanne Kite and Robbie Wing
Cape Town's Rastafarians – Kofi Hope
Conjay's First Walk Home – Tura Cousins Wilson and Shane Laptiste
Another Fine Mess on Regionalism – Sabine Matheson
The Palimpset of Heritage Streetscapes – Tatum Taylor Chaubal
Protecting a Queer Beach – Wesley Reibeling
Public Health in the Post-COVID Era – Andrew Boozary
Why Can't We Sell Stuff Anyplace? – John Lorinc
The Messy Culture of Graffiti – Dylan Reid
An Indigenous Take on the 15 Minute City – Carolynne Crawley
Thinking Twice about Consultation – Lorne Cappe
What is safety? – Kimahli Powell
Conclusion – Dylan Reid, Leslie Woo, Zahra Ebrahim, and John Lorinc