Illustration by Sarah Farquhar
In a recent social media post titled “POV: your eccentric friend who turns objects into accessories,” New York-based comedian Jessie Jolles can be seen perching a glittery piece of bunny rabbit Easter decor atop her head. The look recalls the signature styling gesture of an eccentric beloved by the 1990s fashion set, Isabella Blow, an aristocrat for whom wearing the whimsical wares of British milliner Philip Treacy was part of daily life.
Unlike Blow, though, Jolles isn’t sitting front row at a runway show while wearing her outré garb. In this Reel, she’s in a run-of-the-mill craft store decked out in a body-conscious leopard print dress and leopard-and-floral fun fur coat. She struts around the streets of New York with a singular confidence, filming herself trying on knick-knacks in a dollar store as if they were the latest bizarre baubles from the French surrealist fashion house, Schiaparelli (its founder, Elsa, was an equally wacky fashionista).
While the average observer might raise an eyebrow, the style world has long adored such eccentric types. There was the late entrepreneur Iris Apfel, one of Jolles’s style icons, who was dubbed the “rare bird of fashion.” The runway reporter Anna Piaggi had a penchant for bold hats, which she wore atop her well-powdered and rouged face for much of her life. Vogue editor Andre Leon Talley’s commitment to voluminous silhouettes is still revered. And Leigh Bowery, the late Australian performer, designer and club promoter who’s the current subject of an exhibition at the Tate Modern in London, had a Club Kid look that was one part Oscar Wilde and one part Marie Antoinette.
This spring fashion brands are championing outside-the-box dressing, as seen in Marc Jacobs’ bulbous silhouettes.Dan Lecca/Supplied
Chopova Lowena’s Margaret bag, a collaboration with Hellmann’s that’s designed to carry an actual jar of mayonnaise.Supplied
This spring, fashion brands are championing equally outside-the-box dressing. Marc Jacobs has his bulbous silhouettes and Charles Jeffrey Loverboy did dishevelled English dandy. Chopova Lowena released its Margaret bag, a collaboration with Hellmann’s that’s designed to carry an actual jar of mayonnaise. Its nearly $3,000 price tag (and another viral clutch by Moschino that resembles a blob of spaghetti) implies there’s still a consumer appetite for kooky clothes and accessories.
Via a video call from her knickknack-filled apartment, Jolles says that she began to make her flamboyancy-focused content after working as a strategist and creator for clients. “I thought, ‘why can’t you do this for yourself,‘” she says. “There came a reckoning that I have to learn to believe in myself. So, I gave permission to be my weird self on the internet.”
At first, she says that people weren’t paying too much attention to her brassy comedic bits, which often draw focus to her myriad collections of clothing and decor. But now, her fledgling following has grown to over 125,000 on Instagram. Finding fame and possible fortune isn’t the primary objective for Jolles, who says her personal style journey evolved after grappling with an eating disorder. “For years when I got dressed, I was trying to hide my body and, really, who I was,” Jolles says. “I just wanted to blend in. But then, you know, you get to a point where you really love yourself and want to wear all these beautiful things.”
Jolles points to the concept of dopamine dressing as a by-product of her sartorial proclivities. “The world can be a scary place, and aggressively seeking joy is such an act of defiance,” she says. “That’s something that, at this point, I try to focus on for myself every day.” That philosophy is likely why she and other fashion eccentrics like the Green Lady of Brookyln (the moniker of an elderly Nova Scotian-born textile artist named Elizabeth Eaton Rosenthal who wears only one colour) are finding popularity as unlikely provocateurs.
Jolles relishes the messages she receives from fans who’ve come to feel more empowered since seeing her videos but dressing eccentrically can also draw negative attention. “Public reactions to eccentric dress vary widely because such expressions can provoke deep-rooted social and psychological responses,” says Dr. Carolyn Mair, a fashion business consultant and the author of The Psychology of Fashion. “Those who value creativity, openness or nonconformity often respond with admiration or curiosity. Conversely, others may react with discomfort or disapproval, often because eccentric dress disrupts the social expectations they’ve internalized. It may evoke a fear of the unfamiliar or be perceived as a threat to social order.”
A dishevelled English dandy look by Charles Jeffrey Loverboy.Supplied
Vanja Vasic, founder and director of the Fashion Art Toronto platform, which stages its next fashion week from May 29 to June 1, has created a haven for unconventional designers and dressers over the event’s 20-year history. Off the runway, its audience represents lovers of creativity turned up to 11. “I wanted to create a space for play with fashion,” Vasic says. “A space that allows people to push boundaries and not follow typical beauty standards.” Vasic sees her own sense of style as a way to connect with people. “I can do that through fashion and the way I dress,” she says. “It’s a way for people to see me, and for me to see them.”
This is maybe the most compelling thing about eccentrics and what we can learn from how they style themselves. As Dr. Mair notes, “ultimately, the way people respond to eccentric dress says much more about their own values, assumptions and insecurities than it does about the individual choosing to stand out.”
