Bewigged – Greg Bailey’s Post-colonial Paraphernalia

Greg Bailey – Lady Locks (2021)

I am privileged to have been invited to curate the debut solo exhibition of the Jamaican artist Greg Bailey is entitled Post-Colonial Paraphernalia. The exhibition explores the lingering effects of colonial symbols and and features ten new oil paintings and one drawing. The exhibition is on view at Creativ Space, 2 Windsor Avenue, Kingston 5, from Wednesday, December 8 to Wednesday December 22, 2021, from 11 am to 6 pm, Mondays to Fridays. Below is my curatorial essay on the exhibition and you can click the links to peruse Greg Bailey’s bio and statement and the exhibition catalogue list.

For the master’s tools will never dismantle the master’s house. They may allow us temporarily to beat him at his own game, but they will never enable us to bring about genuine change.

Audre Lorde

It was clear that Greg Bailey would be an artist of significance from the moment he graduated from the Edna Manley College. An accomplished realist, figurative painter, he immediately positioned himself as an astute and sophisticated social commentator, whose work engages the complexities and contradictions of life in post-colonial Jamaica. He is a key representative of a strong group of representational painters in contemporary Jamaican art, along with Phillip Thomas, Alicia Brown, Michael Elliott, Kimani Beckford and others.

Greg is mainly a painter of the human figure, and he is best known for his portraits, which often feature friends and members of his family, or himself at different ages. With few exceptions, his portrayals are not conventional portraits, focused on the likeness and psychology of his sitters. While the individual identities of the persons portrayed are not insignificant to him, his portraits are sardonic visual parables that lucidly probe the fundamental problematic of post-coloniality.

Greg Bailey – Boasy Slave (2014)

Internalized Oppression

I regard Greg Bailey’s large portrait Boasy Slave (2014) as a signal work that marks the start of his current trajectory. The work features a black man, in a crisp suit, seated quite casually in a gilded, formal antique chair in an abstracted interior that suggest affluence and status. The painting was selected for the National Gallery of Jamaica’s 2014 Jamaica Biennial, of which I was the lead curator, and featured in the satellite exhibition at Devon House, where we brought the biennial works into dialogue with the context and history of that historic mansion. We installed Boasy Slave in the formal dining room, and provocatively mounted it in the place where the large standing portrait of the colonial lieutenant-governor and planter Peter Beckford normally hangs. The substitution brought out the contradictions of Devon House itself, as the elegant suburban mansion that was built and owned by Jamaica’s first black millionaire, and as such represents a seminal challenge to the colonial social order and a key symbolic step in the emergence of post-colonial Jamaica, but nonetheless emulates the style and grandeur of the plantation-era Great House many years after slavery was abolished. The contradictions under discussion here indeed have a long history.

But who is this Boasy Slave who sits so confidently and defiantly in what could well have been the chair of a slave master? Greg told me that he is the archetypal post-colonial politician, a slippery, conflicted, and self-serving figure who is more concerned with negotiating his own position (and this archetypal politician is usually a “he”) in a social and political dispensation inherited from the colonial era, than with dismantling the lingering colonial hierarchies and old and new structures of oppression. He wears the right designer suit, shirt, shoes, and tie, and, yes, argyle socks.

His persona and mode of dress are symbolic expressions of the stifling, self-defeating aspirational mentality that has overtaken post-colonial Jamaica, despite well-meant but ultimately ineffectual and short-lived attempts in the 1960s and 1970s to foster a more egalitarian society and to decolonize civic life. This aspirational posture also conceals the fact that our “archetypal politician” has consistently failed to deliver on his campaign promises or to provide the inspired leadership to take the country in new and productive directions that would allow it to live up to the early promise of Independence. As Greg Bailey noted in a recent conversation, it is simply absurd that election campaign platforms in 21st century Jamaica should still involve promises of such basic amenities as piped water and paved roads. Despite his knee-jerk posture and rhetoric of post-colonial defiance, Greg Bailey’s Boasy Slave figure is not a culture hero, but an agent of self-inflicted post-colonial failure.

Audre Lorde has rightly cautioned that “the master’s tools cannot dismantle the master’s house.” As Boasy Slave reminds us, there is a thin and tenuous line between the subversive appropriation of the symbolic trappings of colonial and post-colonial power and their conscious or unconscious perpetuation. While the former may represent an eloquent challenge to established power in the moment, Lorde reminds us that such a strategy is not sustainable in the long run, and all too easily shades into the witting or unwitting perpetuation of the underlying hierarchies and systems. Perpetuating and promoting symbols of oppression represents a nefarious, psychologically damaging form of symbolic violence, which is internalized in a way that results in a deeply conflicted sense of self and helps to reproduce the socio-political order with which it is associated. Frantz Fanon called it internalized oppression, a psychological condition whereby the victim of such symbolic violence is also its own perpetrator and stands firmly in the way of renewal and change.

The current decolonial iconoclastic fervour, whereby colonial monuments all over the world have been destroyed, damaged, or formally removed, is rooted in this recognition that symbols of social and political power hold great and potentially damaging psychological power over us. A major historical reckoning is in progress, but its outcome is as yet uncertain, and post-colonies like Jamaica have been remarkably slow and timid in participating, despite the earlier history of decolonial activism and resistance which has resulted in globally influential cultural forms such as reggae music.

It is certainly ironic that Barbados, once labelled as “Little England,” became a republic before Jamaica. Barbados furthermore removed its main colonial statue, of Lord Nelson, in 2020 and initiated a major public art project at the new Golden Square Freedom Park. Barbados has also just announced the establishment of a Museum of Transatlantic Slavery, to be designed by the noted Ghanaian-British architect Sir David Adjaye. It appears that Jamaica has surrendered its leadership role, in the Anglophone Caribbean, in shaping decolonial ideology, culture and political action to Barbados, even though this is a role Jamaica long took for granted. The question arises why there is this lingering hesitancy in Jamaica to take the process of decolonization to its inevitable and indeed necessary conclusions, while others in the region are making remarkable headway. One is the present lack of inspired leadership, but it may also well be that the beneficiaries of this internalized oppression complex are loathe to surrender their largely unearned privileges and status.

This sort of self-perpetuating and paralyzing internalized oppression is a central theme in Greg Bailey’s work, and it is no coincidence he has turned his attention to the lingering post-colonial obsession with ceremonial wigs, gowns, insignia, and titles in his current body of work, collectively titled Post-colonial Paraphernalia. The impetus for this new body of work was the shock and debate caused by the decision of the newly appointed Speaker of the House in Jamaica’s Parliament in 2016 to adopt the traditional, colonial-style wig associated with that office in the former British Empire, after the practice had been largely abandoned for years.

Peruques and Periwigs

Wigs have been worn at various moments in human history, for cosmetic and ceremonial reasons, and they are often associated with social rank and power. Ancient Egypt is one early example of a society in which formal wigs were associated with high status. In Europe, the wearing of powdered wigs became fashionable in the 16th and 17th century, for men and for women, and was well-established by the 18th century. While initially, and rather inauspiciously, associated with efforts to conceal syphilis-related hair loss, the so-called periwigs or peruques (after the French) were high fashion in 18th century Europe. Extravagant themed wigs were worn to balls and coronations, such as Marie Antoinette’s wig with curls styled like sea waves and with an actual model ship incorporated, which was created and worn to honour a French naval battle victory. This extravagant wig fashion was spoofed mercilessly by William Hogarth in his 1761 engraving The Five Orders of Perriwigs [sic] as they were Worn at the Late Coronation Measured Architectonically. But even on less formal occasions, a “well-bred” European of that era was not “dressed” without wearing at least a basic, half-bob periwig.

Philip Wickstead – Portrait of Benjamin and Mary Pusey, c1775, National Gallery of Jamaica

Full-sized periwigs were quite expensive – the current equivalent cost is about US$ 10,000 and they required regular maintenance and the removal of lice, which added to the cost. Only the privileged could afford them. Not all persons who wore periwigs were however of high social standing: they were for instance also worn by liveried servants and footmen, as part of their uniform, although this merely signified their proximity to power and status, and furthermore rendered the wearer anonymous, by removing their individual visual identity. It was inevitable that the practice would also spread to the colonies, even in climates where the wearing of such periwigs was particularly uncomfortable, as is illustrated by extant portraits of planters and colonial officials in places such as Jamaica. In this context, powdered wigs became more specifically associated with colonial and plantation power, an association such wigs retain today.

Powdered wigs went out of fashion in the late 18th century, at the end of the Ancien Régime, but their formalized incarnations lived on in association with certain offices, for instance as part of the traditional courtroom attire of judges and barristers, especially in criminal cases. The main argument in its favour is that wigs and gowns acknowledge the solemnity of the occasion and emphasise the office and function of the bewigged rather than his or her individuality, thus providing an air of unbiased objectivity. That English judges do not wear wigs in court cases involving children, as that may intimidate them, however, inadvertently acknowledges the symbolic terror, dehumanization, and assertions of unquestionable power that emanate from such attire. The archaic practice of bewigged functionaries has been particularly persistent in the United Kingdom and its former colonies but is now finally on its way out, and the subject of significant debate, which has been amplified by the current decolonial movement.

A Wah Dis?

The question of whether such colonial wigs should be worn in contemporary Jamaica was acutely posed in 2016 when the newly appointed Speaker of the House, Pearnel Charles, appeared in full regalia in Parliament, wearing not only the traditional gown but also the wig. One opposition Member of Parliament loudly and mockingly exclaimed “a wah dis?” The matter caused significant mirth in Parliament and was eagerly pounced upon by the media, leading to much debate about the undeniable backwardness of the gesture. Pearnel Charles, while obviously “on the backfoot” (to use Jamaican parlance for being on the defensive), however made some interesting points in his response. He said in an interview with the Jamaica Observer:

One of the reasons why I am not worried about wearing the [wig] and gown is that it is assigned to the Speaker. The gavel and mace are two instruments to guide the Speaker, with the mace being the more important, as the Parliament cannot be in session without it.… [A]s long as we are under the British Monarch, we should follow the rules. I have no feeling that if I take off the wig and gown, I will be less neo-colonial. People say we are independent, but independent of what? (April 23, 2016).

The wig is indeed just the tip of a massive iceberg of symbolic colonial holdovers, some of them visible and tangible, some subliminal, and some so naturalized and ingrained in the local culture that they may appear to be authentically Jamaican, such as the extreme, persnickety preoccupation with titles and protocol, and the endless, formalized ceremonial that makes public events so excruciating in this country. Charles’ comments also highlighted Jamaica’s ambiguous status as a supposedly independent post-colony, which still has the British monarch as its head of state.

Interestingly, Charles was not the only parliamentary official in Jamaica who opted to be bewigged in recent times: the former President of the Senate, Oswald Harding, wore the wig for many years, until his retirement in 2011, just five years before Pearnel Charles and curiously resulting in far less public commentary or mockery by his peers. Could it be that Harding’s lighter skin, and hence his more secure elevated social status, made him less vulnerable to such mockery than the black Pearnel Charles, and deemed a more legitimate heir of the trappings of colonial power and hierarchy? The conflicted relationship of these symbolic colonial hangovers to contemporary conceptions of race and social status is central to the problematic under discussion here.

Decolonial Painting

Greg Bailey’s Postcolonial Paraphernalia series consists of portraits of friends and family members who are all bewigged, with barrister or parliamentary wigs, although the child in Antithesis holds a wig in his hands instead. Most of the sitters wear their own regular clothes, which significantly contributes to the incongruous, surreal quality of the images. One, in The Order of St Adrian, wears a casual “ganzie” along with an Elizabethan collar, which further adds to the visual dissonance. There are six smaller portraits and four larger ones in the exhibition although the series is ongoing and includes a few other completed works.

Giovanni Bellini, Portrait of the Venetian Doge Leonardo Loredan (1501-1502), Collection: National Gallery, London, image source: Wikimedia

The smaller portraits are formally posed, in the sort of standardized frontal, three-quarter and profile poses that were codified in the Renaissance European painting, and the expressions of the sitters are stern and impassive. Some of the wigs they wear are carefully coifed while others show signs of wear and tear, which sends its own subliminal messages. There is a still, almost airless, and monumentalized quality to the portraits, which recalls the portrait of the Venetian Doge Leonardo Loredan (1501-1502) by Giovanni Bellini, with which they also share a strong tension between the robust three-dimensionality and trompe l’oeil effect of the figures and head-dresses; the shallow, intensely lit space in which the portrayed figures dwell; and the abstracted two-dimensionality of the background. In Greg Bailey’s portraits, however the background is not flat but subtly patterned with subliminal, quasi-embossed symbols that include slave ships, Jamaican national symbols, symbols of justice, palm trees, dread-locksed profiles, and allusions to the sort of upscale brand logos that have become an iconic, and equally contradictory and aspirational part of Black modernity.

Greg Bailey – Lady Madam Q.C. (2020)

This play between history and modernity and between compliance and resistance is amplified in Lady Madam QC (2020) where the Mondrian-style blouse worn by the female subject which complicates the symbolic, cultural, and visual tensions even further. The monumentality of the figures in the portraits is significant too and emphasized by the sharply cast shadows that reinforce the materiality of the figures and wigs, while taking on a life of their own as ghostly presences. This monumental quality relates to Greg Bailey’s MFA research into the need for a black representational challenge to the dominant white monumentality that was inherited from colonialism and institutionalized racism. The assertive visual presence of his sitters indeed suggests an assertive sense of self, despite, and independent from the confounding symbols of oppressive power that surround them. This suggests that they are no mere “boasy slaves” but strong individuals who at least have the agency and psychological tools to navigate, challenge, and change the fraught symbolic terrain and power structures in which they operate.

Greg Bailey – Antithesis (2021)

While the other portrait subjects are adults, the series includes three larger portraits of children – Antithesis, The Order of St Michael, and Mad-allion, all from 2021 – for which Greg Bailey asked young cousins and nephews to pose with ceremonial gowns and wigs. As full-figure portraits, the children stand in a slightly deeper spatial context and on ornate carpets that simultaneously add depth and two-dimensionality, while adding to the visual and symbolic complexity of the images. Here the expressions are not at all impassive, and the vulnerability of the subjects is acknowledged, as the children look perplexed and overwhelmed by the paraphernalia they were asked to wear. They more acutely and openly reveal the contradictions involved, as the gowns and wigs more obviously do not fit them, and their very expressions question and resist the paraphernalia they are engaging with – another signal that internalized oppression can in fact be challenged providing there is sufficient awareness.

The eponymous Postcolonial Paraphernalia, which is the largest work in the current exhibition and the only painting in which more than one figure appears. In this work, a fashionably Jamaican suited figure is being fitted with a periwig, while having a very British spot of tea. The main figure appears indifferent, and even resigned, but the images and insignia on the carpet and in the background – the Garveyite flag and Black Star, a medallion with a slave ship, a map of the Americas, and the Rastafarian Lion of Judah – all allude to the symbolic wars that are being fought over his body and person. It is in many ways a summary piece of the series.

If we take Audre Lorde’s cautionary words seriously, however, we must also query Greg Bailey’s use of the painting styles, techniques, and conventions Renaissance Tradition, as this could also be a case of “using the master’s tools.” In fact, it raises broader questions about the current trend of portraits of black subjects in period costumes and poses and contexts derived from the Renaissance Tradition, which appears to have started with Kehinde Wiley and has been followed by a multitude of painters and photographers in Africa and the African Diaspora. The appeal of such images is also obvious in costume dramas such as Bridgerton on Netflix. While such appropriations can make powerful, provocative statements, there is also a facile glibness about many of them, as a sort of shallow racial and cultural cosplay. At their worst, they re-exoticize the black subject in ways that are visually and conceptually seductive but do not engage substantially with the critical issues at hand.

There is no such seductive glibness in Greg Bailey portraits, which unapologetically own and convey their ambivalent socio-political content. His work, and the present body of work especially, embraces its own, inherent representational ambivalence and invite us to reflect more deeply, and unsparingly, on the represented and embedded contradictions, while plotting ways to overcome them.


“The Rise and Fall of the Powdered Wig.” American Battlefield Trust, May 26, 2021, updated April 15, 2021 (, accessed December 2, 2021)

“Court Dress.” Wikipedia (, accessed December 3, 2021)

HG Helps. “Pearnel Sticking to His Wig.” Jamaica Observer, “, accessed December 3, 2021)

Audre Lorde. The Master’s Tools Will Never Dismantle the Master’s House. London: Penguin Classics, 2018.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Blog at

Up ↑

%d bloggers like this: