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Dressing Up: Transvestism and Drag: The History of an Obsession

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Book by Peter Ackroyd

160 pages, Paperback

First published January 1, 1979

156 people want to read

About the author

Peter Ackroyd

188 books1,500 followers
Peter Ackroyd CBE is an English novelist and biographer with a particular interest in the history and culture of London.

Peter Ackroyd's mother worked in the personnel department of an engineering firm, his father having left the family home when Ackroyd was a baby. He was reading newspapers by the age of 5 and, at 9, wrote a play about Guy Fawkes. Reputedly, he first realized he was gay at the age of 7.

Ackroyd was educated at St. Benedict's, Ealing and at Clare College, Cambridge, from which he graduated with a double first in English. In 1972, he was a Mellon Fellow at Yale University in the United States. The result of this fellowship was Ackroyd's Notes for a New Culture, written when he was only 22 and eventually published in 1976. The title, a playful echo of T. S. Eliot's Notes Towards the Definition of Culture (1948), was an early indication of Ackroyd's penchant for creatively exploring and reexamining the works of other London-based writers.

Ackroyd's literary career began with poetry, including such works as London Lickpenny (1973) and The Diversions of Purley (1987). He later moved into fiction and has become an acclaimed author, winning the 1998 James Tait Black Memorial Prize for the biography Thomas More and being shortlisted for the Booker Prize in 1987.

Ackroyd worked at The Spectator magazine between 1973 and 1977 and became joint managing editor in 1978. In 1982 he published The Great Fire of London, his first novel. This novel deals with one of Ackroyd's great heroes, Charles Dickens, and is a reworking of Little Dorrit. The novel set the stage for the long sequence of novels Ackroyd has produced since, all of which deal in some way with the complex interaction of time and space, and what Ackroyd calls "the spirit of place". It is also the first in a sequence of novels of London, through which he traces the changing, but curiously consistent nature of the city. Often this theme is explored through the city's artists, and especially its writers.

Ackroyd has always shown a great interest in the city of London, and one of his best known works, London: The Biography, is an extensive and thorough discussion of London through the ages.

His fascination with London literary and artistic figures is also displayed in the sequence of biographies he has produced of Ezra Pound (1980), T. S. Eliot (1984), Charles Dickens (1990), William Blake (1995), Thomas More (1998), Chaucer (2004), William Shakespeare (2005), and J. M. W. Turner. The city itself stands astride all these works, as it does in the fiction.

From 2003 to 2005, Ackroyd wrote a six-book non-fiction series (Voyages Through Time), intended for readers as young as eight. This was his first work for children. The critically acclaimed series is an extensive narrative of key periods in world history.

Early in his career, Ackroyd was nominated a Fellow of the Royal Society of Literature in 1984 and, as well as producing fiction, biography and other literary works, is also a regular radio and television broadcaster and book critic.

In the New Year's honours list of 2003, Ackroyd was awarded the CBE.

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Displaying 1 - 6 of 6 reviews
Profile Image for Ed Erwin.
1,221 reviews131 followers
April 8, 2021
This book is very dated and often offensive. Some will find it impossible to read, and I understand that. On the other hand, I recently read a recently-published book by a heterosexual male cross-dresser who says the many historical examples in this book helped him feel more confident and helped him come to terms with himself.

The first chapter is the most offensive. It offers various different theories about why people cross-dress. The emphasis is on men who dress as women and the theories are basically different ways of trying to understand what sort of trauma or mental illness would make someone want to do that. Freud's nonsense plays a big part. Feel free to skip this chapter.

After that the offensive attitudes are toned down. The descriptions of the lives of various historical figures is quite interesting. I also greatly enjoyed the chapter on drag, in which I found out about many early artists I hadn't known about. I've been enjoying researching them on wikipedia and looking for performances on YouToob.

Many great pictures and references to follow-up on make this still a valuable resource. The author's theories, though, belong in the trash.
Profile Image for Preetam Chatterjee.
7,447 reviews433 followers
January 28, 2026
Reading Peter Ackroyd’s 'Dressing Up' felt uncannily like reading a secret history that had always been there, humming beneath the official narratives of culture, art, religion, and power.

It is not a book about clothing in any narrow sense, nor even strictly about transvestism or drag as contemporary identity categories. It is, rather, a book about disguise as a civilizational impulse — about humanity’s long, restless fascination with stepping outside itself and discovering, sometimes with delight and sometimes with terror, that the self is far less stable than it pretends to be.

Ackroyd approaches the subject obliquely, almost mischievously. He does not build a linear argument or announce a thesis that he then proceeds to prove. Instead, he wanders.

He accumulates anecdotes, historical moments, theatrical episodes, religious rituals, scandals, literary obsessions. The book reads less like cultural history and more like a cabinet of curiosities, and this is precisely its strength.

Dressing up, Ackroyd suggests, cannot be explained without being enacted. The form of the book mirrors its subject: layered, performative, resistant to a single identity.

What struck me immediately was how far Ackroyd refuses to confine the phenomenon to modern sexuality or contemporary politics. Long before drag became a site of ideological warfare, it was already embedded in ritual, theater, monarchy, and crime.

Ackroyd begins in the ancient world, where cross-dressing appears not as deviance but as sacred inversion. Gods change sex, priests adopt female attire, rituals require the suspension of fixed identity. In these contexts, transvestism is not rebellion but access — a means of touching the divine by stepping outside the ordinary order.

This sacred dimension lingers throughout the book like a suppressed memory. Even as societies secularize, the aura remains. Dressing up retains something uncanny, something that unsettles because it exposes how much of identity is costume to begin with.

Ackroyd is particularly good at tracing this continuity without ever stating it explicitly. He trusts the reader to feel the pattern rather than be instructed in it.

The theatrical tradition occupies the book’s emotional core. From Greek drama to Elizabethan theater to pantomime and music hall, Ackroyd shows how cross-dressing was not marginal but central to performance itself.

In Shakespeare’s England, all female roles were played by boys. Gender was already a layered fiction: a boy playing a woman who sometimes disguised herself as a man. Ackroyd delights in these recursive disguises, not because they are clever but because they expose the artificiality of gender long before modern theory arrived to name it.

Reading this alongside Judith Butler or contemporary gender theory is almost unnecessary. Ackroyd achieves a similar destabilization historically rather than philosophically. He does not argue that gender is performance; he shows that it has always been performed. The effect is more persuasive precisely because it avoids abstraction.

Yet the book is not celebratory in any simplistic sense. Ackroyd is acutely aware of the fear and violence that often accompany transvestism. The same societies that delighted in theatrical cross-dressing criminalized it in daily life.

Laws against disguise, sumptuary regulations, moral panics — these recur with numbing regularity. Dressing up becomes dangerous when it escapes ritual containment. When disguise migrates from stage to street, it threatens hierarchy itself.

This tension between permitted performance and forbidden reality runs throughout the book. Ackroyd is especially incisive on this point in his discussion of monarchy. Kings and queens dressed as symbols long before they dressed as individuals. Royal clothing was never merely decorative; it was metaphysical.

To dress like a king was treasonous because it challenged the idea that authority was embodied rather than enacted. When commoners dressed above their station, the anxiety was not aesthetic but ontological.

This is where the book becomes unexpectedly political. Ackroyd does not frame his analysis in terms of power explicitly, but power saturates every example.

Dressing up exposes how authority relies on costume, ritual, and spectacle. Strip these away, and the sovereign becomes just another body. In this sense, drag is not parody but revelation.

The literary sections of the book are among its richest. Ackroyd moves effortlessly from Defoe to Dickens, from masquerade novels to Gothic fiction. Disguise becomes a narrative engine. Characters cross-dress to escape, to deceive, to survive.

What fascinated me was how often these disguises fail not because they are unconvincing but because the world refuses to accept ambiguity. The danger lies not in the disguise itself but in the moment it is recognized.

Ackroyd’s discussion of criminal transvestism — thieves, spies, fugitives — adds another layer. Here, dressing up is tactical rather than expressive. Identity becomes a tool.

Gender is not explored; it is exploited. And yet, even here, the anxiety remains. Authorities fear disguise because it reveals how easily surveillance can be evaded, how fragile social legibility really is.

One of the book’s most unsettling undercurrents is its suggestion that obsession, not identity, drives the phenomenon. Ackroyd uses the word obsession deliberately. He is less interested in stable categories of self than in repetition, compulsion, fascination.

People dress up not always because they want to be something else, but because they cannot stop returning to the threshold between selves.

This framing feels deeply postmodern, though Ackroyd never uses the term. Identity in 'Dressing Up' is not a destination but a loop. Individuals cross boundaries only to circle back, changed but unresolved.

There is no narrative of progress, no march toward authenticity. Instead, there is recurrence — the same gestures appearing across centuries under different names.

Reading this in the present day, amid fierce debates about gender identity, drag performance, and cultural legitimacy, was a disorienting experience. Ackroyd’s book refuses to be conscripted into contemporary arguments. It neither defends nor condemns. It historicizes. In doing so, it destabilizes the urgency of the present by revealing how old the anxiety really is.

This does not mean the book is politically neutral. On the contrary, its refusal to moralize is itself a stance. Ackroyd treats obsession as a fact of culture, not a problem to be solved.

This can feel evasive to readers seeking affirmation or critique. But it also prevents the book from becoming dated. Ackroyd writes not for the moment but against it.

Stylistically, 'Dressing Up' is unmistakably Ackroyd. The prose is elegant, allusive, slightly aloof. He prefers suggestion to declaration. At times, this restraint borders on frustration.

There are moments when one wishes he would linger longer, analyze deeper, push harder. But this withholding is part of the book’s method. Ackroyd wants the reader to feel the accumulation rather than be handed conclusions.

The book’s episodic structure reinforces this effect. Chapters feel like scenes rather than arguments. One moves from ancient ritual to Renaissance theater to Victorian scandal with little connective tissue. And yet, by the end, a pattern emerges.

Dressing up persists because it addresses something fundamental: the instability of identity itself.

Comparatively, the book sits at an interesting crossroads. Unlike academic gender studies, it avoids theoretical vocabulary. Unlike memoir or contemporary reportage, it avoids emotional immediacy. And unlike moral history, it avoids judgment.

This places it closer to cultural archaeology than critique. Ackroyd excavates rather than interprets.

Reading it alongside Michel Foucault’s histories of sexuality made the difference stark. Where Foucault anatomizes power through discourse, Ackroyd traces obsession through anecdote. Foucault dissects; Ackroyd collects. Both approaches reveal truth, but in different registers. Ackroyd’s method is messier, less systematic, but more atmospheric.

There is also something distinctly English about the book. Ackroyd’s sensibility — steeped in London, theater, eccentricity — shapes his selection.

France, Italy, and the ancient world appear, but England dominates. This is not a flaw so much as a lens. English culture, with its obsession with class, propriety, and performance, becomes an ideal laboratory for studying disguise.

The London streets Ackroyd evokes are spaces of masquerade: carnivals, pleasure gardens, theaters, alleyways. The city itself becomes a costume — a place where anonymity enables transformation.

Reading this, I was reminded of Walter Benjamin’s flâneur, drifting through urban spectacle, half-observer, half-performer. Dressing up is not always deliberate; sometimes it is absorbed through environment.

One of the book’s quiet achievements is its refusal to psychologize excessively. Ackroyd does not speculate about inner lives beyond what historical records allow.

He resists the temptation to retroactively diagnose. This restraint is ethically important. It prevents the past from being flattened into contemporary categories.

At the same time, this refusal can feel emotionally distant. There are moments when the human cost — persecution, humiliation, violence — flickers briefly and then recedes. Ackroyd acknowledges suffering, but he does not dwell in it. The obsession he traces is cultural, not personal. Readers seeking empathy may find this limiting.

For me, this distance was productive. It forced me to confront my own desire for moral clarity. Ackroyd denies that comfort. He shows that culture produces obsessions that cannot be neatly redeemed or condemned.

Dressing up persists because it satisfies something that societies both need and fear.

The postmodern quality of the book lies precisely here: in its refusal of resolution. Identity remains unstable. Meaning remains contingent. History does not progress toward enlightenment but loops through repetition.

Dressing up is neither liberated nor suppressed; it is reconfigured endlessly.

By the time I finished the book, what lingered was not information but unease. Ackroyd had quietly dismantled the idea that identity is something one simply possesses.

Instead, identity appears as something one wears, removes, alters, and returns to — sometimes joyfully, sometimes compulsively.

In a year which has begun with climate collapse, political order, and existential threat, 'Dressing Up' felt oddly grounding. It reminded me that long before the world worried about extinction, it worried about appearance.

About who is allowed to be seen as what. About the terror that surfaces when the costume slips.

Ackroyd does not offer solutions, solidarity, or slogans. He offers history as disturbance.

And in doing so, he creates a book that resists capture by the moment in which it is read.

'Dressing Up' is not a manifesto. It is a mirror — cracked, layered, and impossible to look into without seeing the seams.

And perhaps that is its deepest insight: that obsession with disguise endures because, at some level, we already know the truth it reveals.

That the self has always been dressed.

A highly recommended classic.
Profile Image for HM.
16 reviews
October 7, 2017
Could not stomach this book. Did not expect it to be so homophobic, gender-centric, misogynistic, so white-privilege and heterosexual. Honestly, girl, stay away from this book--unless you are studying the erroneous state of mind behind the criminalization of homosexuality.
Profile Image for Joseph Hirsch.
Author 51 books134 followers
March 23, 2018
This cursory overview of transvestism does a decent job of summarizing the different forms of the lifestyle (hetero- vs. homosexual vs. hermaphroditic) and there are some interesting photos, drawings, frontispieces, etc. That said, it felt as if the author was merely interested in grazing the surface of a phenomenon that (one would think) would be nigh-limitless in its complexity. After some initial groundwork done to define and delineate various transvestite communities, Mr Ackroyd (or maybe "Doctor Ackroyd") deals with different ways various cultures accepted, rejected, or punished cross-dressing. "Dressing up," as the title has it, can be a way for heterosexual men to mock gay or effeminate tendencies, an expression of mixed emotions toward a domineering mother, or a method of making oneself closer to the beloved feminine ideal and the beauty of women (a little too close for some tastes). Transvestism dovetails with drag and overlaps it in confusing ways that the author attempts to clarify, though aside from drag/vaudeville having a satirical element as opposed to the fetishistic and ritualistic act of true transvestites, I'm not sure where the border lies, or where one category ends and another begins. Human sexuality is complex stuff, and Ackroyd seems to extinguish as much light as he casts.

The chapter I found most interesting, dealing with transvestite literature, was, alas, one of the shortest in the book. The book is dated, as other critics have pointed out, but that's no excuse for the short shrift that film depictions of cross-dressing are given (again, where is Edward D. Wood Jr?!)

Lastly, although I am not one for political correctness and don't sweat bullets over mis-gendering someone and ending up in a multicult gulag at some future date, even I as pale penis Putin-esque patriarch found there was a derogatory and sometimes mean-spirited undercurrent to Ackroyd's analysis. His reliance on concepts like "auto-narcissism" to explain the behavior men who wear women's clothing and other such pseudo-Freudian sorties against sympathetic subjects made me feel, at times, like I was reading a DSM manual from the late 50s instead of a brief cultural history from the late 70s. All in all, the book is a bit underdeveloped, but if you're coming to the subject cold (as I was) and are looking for a bibliography to raid, "Dressing Up" is a decent starting point. Those who already know their stuff in this area will find the book to be a mildly insulting retread, more of a cultural artifact than a work that still lives and breathes. Tepid recommendation, in any event.
Profile Image for Cass Lace.
8 reviews
September 8, 2022
-1 for commentary, 2 for historical perspective, 4.5 for some really great photos
Displaying 1 - 6 of 6 reviews

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