Review: The Dress HE Wore (Lift the Lid Theatre)

The title of The Dress HE Wore—a Lift the Lid Theatre production now playing at Red Sandcastle Theatre—alongside its billing (“a provocative and disturbing black comedy”) strongly implies that the show is going to be a focused exploration of the impetus behind crossdressing.

The dress is there – an oversized floral almost-muumuu worn by solo actor Alastair Love’s David – but it’s really incidental, almost ancillary to the plot. Though the character wears a dress, its trappings are merely symbolic, a representation of a dysfunctional relationship he can’t quite let go.

Running a scant 45 minutes, The Dress HE Wore is nevertheless a fascinating look into a nuanced but often unsympathetic character. It’s never boring, but disappointingly relies heavily on stereotypical commentary regarding male and female gender roles.

I’ll be perfectly honest: on the way to the show, my (female) guest and I experienced some particularly textbook and virulent gender-based street harassment. Therefore, I was already more sensitive than usual about the entitled and patronizing perception many men seem to have about women in general. That being said, the show opens with what felt like a near ten-minute rant about how women are all crazy, and fall into either the “angel” or “devil” category (essentially, the virgin/whore dichotomy, which insults both even when touting one via positive stereotype).

This is only presented as the character’s view, but while I’m perfectly capable of separating an unsympathetic character from a good or bad play, I found these “provocative” observations tired and I wasn’t predisposed to enjoy the rest of the show. The opening seemed to be aggressively establishing David’s bona fides as a straight man, though he is wearing a dress and chatting with a man (unseen) in a minimally-appointed gay bar. Ironically, in attempting to create a non-stereotypical character, it falls back on other stereotypes.

In a way, The Dress HE Wore is more a series of vignettes than a play, as David takes us through his tumultuous relationship with former hitchhiker Betty, an uncommonly large woman from Kentucky with a penchant for midnight fishing. It’s in these stories (despite the occasional discomfort), in his discussion of male anger issues, and in a brief foray into addressing the issue of female-instigated domestic violence that I found my interest returning.

In this renewed interest, I also certainly found there to be enjoyable aspects to the piece. In particular, I found Love’s performance to be very compelling in its intensity, particularly his ability to play to the small space with moments of extreme quiet. Though I wanted to know more about why David was at the bar and why we were watching him at this particular moment, I liked the look into his past, as well as his comic renditions of various other characters of varied accent. I credit the performance for the fact that my attention never wavered.

One diversion into a moment from childhood made me wish we could spend more time there, seeing what David was like outside of the pivotal romantic relationship (or before it), along with any other motivation he may have had for donning the dress.

Perhaps the most provocative aspect of The Dress HE Wore is that it subverts expectations by not dwelling that much on the garment in question, giving it a mundane aspect, as something worn to be merely “sensible and efficient.” Stereotype is efficient, too, but I would have preferred instead to see more development of the intriguing character at the play’s core.


  • The Dress HE Wore plays until May 14th at Red Sandcastle Theatre (922 Queen St. East)
  • Shows are Thursday to Saturday at 8pm and Saturday-Sunday at 2pm.
  • Tickets range from $18-25 plus service fee, and can be purchased by calling 416-845-9411, or online.

Photo of Alastair Love provided by the company