Messy Cities: Why We Can't Plan Everything

by Dylan Reid (Editor), Zahra Ebrahim (editor), Leslie Woo (editor)

Would our cities be more lively, more liveable, if we broke the rules more often?

Crowded streets, sidewalk vendors, jumbled architecture, constant clamor, graffitied walls, parks gone wild: are these signs of a poorly managed city or indicators of urban vitality?

With pieces on guerrilla gardening, facadism, queer ecology, and decolonizing public engagement written by experts from all walks of life, Messy Cities makes the case for embracing disorder while not shying away from confronting its challenges.

Messy Cities: Why We Can’t Plan Everything argues that messiness is not a liability but an essential element in all thriving cities. Forty 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.

Genres: Nonfiction, Urbanism, Urban Planning, Urban, Politics, Architecture, Cities

336 pages, Paperback

Published June 3, 2025

Reviews

[Alexander · Rating 2 out of 5]

After an encouraging introduction, you might expect this book to be rich with on-the-ground examples of novel and unconventional uses of city space. Unfortunately, it seems like many authors did not understand the assignment and instead write tangentially about their experience of living in a city.

I definitely agree that often the most desirable parts of a city are those that develop informally. I also think many of the subjects the authors write about are interesting. But most of the time, the authors are either complaining about how their city (usually Toronto) is failing one community or another, or they’re writing about how cities are complex places.

If you’re new to urbanism, or to living in a city, you may enjoy this book.

[Anya Kaplan Hartnett - AKH! · Rating 5 out of 5]

really interesting & informative collection of reads (esp for fans of toronto) my faves were about urban agency, subversive suburban land use, interruptions (relevant to me rn because one of two building elevators is broken so I am meeting neighbors I otherwise would not have), generative and less-generative forms of community conflict, and service dogs navigating flexible streets !

[Isaac · Rating 3 out of 5]

tldr: I wish it spent more time actually grappling with what messy urbanism is, not just addressing topics that are already frequently discussed within Toronto urbanism discourse.

****

Some of the chapters were really interesting and thought-provoking, even for readers who are already steeped in urbanist literature and thought. There were some really interesting perspectives and original contributions to understanding cities (mostly Toronto), how we inhabit them, and what "messiness" can mean. Some highlight chapters for me were Packrat City, Flexible Streets, The Collective Effervescence of Messy Parks, Chaotic Unregulated Tokyo, & The Readable City. These all seemed to clearly understand what the point of the book was and provided interesting and diverse contributions .

Unfortunately for every great chapter there seemed to be a kind of “meh” one. It felt like many of the contributors decided to just write about whatever urbanist topic they felt like, instead of specifically focusing on what “messy urbanism” means. The word “messy” was being stretched pretty thin at some points in relation to the subject matter at hand.

In summary, if you are new to urbanism and city building this can be a fun introductory book. It lets you dip your toes into a wide range of subjects in an accessible way. If you are not new to urbanism, this may not be as exciting…you are gonna encounter a lot of topics you are likely already quite familiar with, instead of getting a chance to truly wrestle with what “messy urbanism” is.

[Prot · Rating 5 out of 5]

Messy Cities is a lovely collection of essays that hammers home the perspective of "messiness". As an aspiring urbanist myself, I think it can be easy to fall into the trap of master planning but in the way "it should be done correctly". I also think that North American urbanism can (pretty fairly I'll admit) focus a-lot on the experience, decay, and regeneration of the traditional downtown core, and how to connect the and "repair" the vast suburban swaths surrounding our cities.

Messy Cities does not provide an explicit thesis, nor a set of policy items to brought into legislature. To make that statement would contravene the theme of the book, messiness. It sheds light on perspectives I think we can be blind too in our crusade to make things better. Are pedestrianized streets that leave *some* access to vehicles really safe for the blind? Should we, when looking at the zoning regulations, also tackle the bylaws that demand leaves be raked? Are those banquet halls and conventention centres in the "pearson airport business-park hell" (my words, not the books) more worthy of adoration than initially thought? Are those industrial business sights, car dependent, and far away, more vital for industrial innovation than "Brampton Innovation District"?

The essays written give me pause, and open perspective on what city living is really like, millions of separate lives, brought together in space, and experiencing many different stories, such a thing must inherently be messy. But if the city is inherently messy, then trying to destroy messiness (as many bylaws, council decisions, and legislation attempt) is trying to destroy the city itself, no?

To those who want to expand your knowledge of the many different types of urban experience (both Toronto and worldwide, though especially in Toronto) I recommend this book.

[Abyaaz · Rating 5 out of 5]

Excellent primer with essays on various city-related issues and topics. Contains different types/quality of writing, as some pieces are written by practitioners, which might not be to everyone’s tastes. Takes a far broader geographical reach than most city books, not bound by North America and western Europe.

Highlights for me:
- ‘Desire lines’ in cities
- Effective public consultation for contentious topics
- The value of intangible culture - case study of GTA banquet halls
- CDMX & Tokyo mixed-use zoning — many pieces on how other places do mixed-use better (unsurprising)
- Essays on safe injection sites and the housing crisis as a health crisis
- Built environment and containment in occupied Palestine

[Brianna Davies · Rating 5 out of 5]

A hopeful end of year read. So much optimism and realism and criticism but every entry had a through line of a love for our cities and a wish to make it work, whatever the means. I particularly loved the essay about living in community in cities and that friction isn’t a downside of living closely with others but something that is expected when you’re actually getting to know your neighbours and trying to be in community. I’m always reminded that avoiding conflict isn’t an option unless you don’t want to do any work at all.

Very grim reading Dr. de Villa’s a passionate plea for better understanding of the necessity of safe consumption sites post Ford doing all he can to destroy them. Fuck man!!

I love this city, I love the people who love this city!!

[Taamara · Rating 3 out of 5]

I wanted to love this cuz it’s like the hot urbanist book this year but maybe my job made this really annoying to me personally… I think it’s really cute tho it’s a good intro to seeing city planning in a different lens and I think each story was the perfect length! super fun to think about how things are built and what makes neighborhoods unique and functional!

[Connor McHugh · Rating 4 out of 5]

Great personal stories from Canadians with different backgrounds regarding messy urbanism. Their stories provide the reader with different lenses through which community, culture, equality and health are represented as interconnected pillars of urban life.

[Manouane Beauchamp · Rating 3 out of 5]

Recueil de textes qui explore l'idée que le désordre et l'imprévu ne sont pas des défauts à éliminer dans une ville, mais des éléments essentiels qui contribuent à sa vitalité, son dynamisme et son inclusivité. À sa façon, chacun des auteurs remettent en question la tendance moderne à sur-planifier et à réglementer chaque aspect de l'environnement urbain.

Livre très intéressant mais certains textes auraient mérité d'être accompagnés par des photos afin de simplifier la compréhension du texte.

[sinclaire :) · Rating 5 out of 5]

Very interesting book with a lot of thoughtful and important concepts and ideas. Highly recommend not just to urban studies people but everyone. Helps think about how we can all come together to make cities more livable.

[Julia Zingel · Rating 4 out of 5]

Enjoyable read

[Kylie · Rating 4 out of 5]

Made me feel sentimental and fondness for Toronto.

[Dylan Grieve · Rating 2 out of 5]

some strong essays but a number of them seemed to lack a link to the theme or speak to a singular topic/issue.

[Isobel Forrest · Rating 4 out of 5]

I loved some of these essays so much. Some were sub par but that’s to be expected.

[Jamie · Rating 3 out of 5]

A collection of essays that’s nominally supposed to be about the positive impacts of less regulated, more organic city planning. But half the contributing authors didn’t seem to get that full concept, and the editors could have been much more discerning in culling what didn’t fit the theme. As it is it’s bloated. There’s a mix of some great essays in here, some that just seem to be someone advertising a program, and some that just ramble about some progressive topic that only occasionally has anything to do with urbanism at all. And it’s way too Toronto-focused.

[Isaiah · Rating 5 out of 5]

A timely addition to a growing collection of urban-centred literature. This book is hard to put down and offers an array of perspectives on what messy urbanism can look like; both intentional and non-intentional. The authors envision a future for city-building that takes the onus off planning and puts it back on the community, in a spirit of accepting that we don’t always have it all together, and that’s OK. As Faui Masoud put it in his chapter titled Dixie Road, “it is no coincidence that some of the most dynamic and beloved areas of urban regions are older ones that fall outside the standardized regulatory underpinnings of typical planning, zoning, and transportation engineering.” As a planner myself, I welcome it — bring on messy cities.