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Some say style is superficial, but the real secret to switching up your look runs deep. Odessa Paloma Parker, a former personal shopper, discovers the importance of taking stock emotionally and evaluating your 'cultural inventory.'

Benjamin MacDonald/The Globe and Mail

Illustrations by Benjamin MacDonald

From garish lighting to pushy salespeople, venturing out to purchase new clothing has its share of challenges. None are more perplexing, though, than the inability many shoppers have to making over their style, despite their wanting to. If you've ever wondered why you can't break away from the neutral palette or basic black garments you tend to wear, it's likely for a reason deeper than wanting to blend in with the crowd. You're actually responding to cultural signals that are embedded in our collective conscious.

"We present and express something about ourselves with our clothing and accessories – that's the external influence," says London-based psychologist Kate Nightingale. She founded Style Psychology Ltd, a consultancy firm whose client list includes U.K. retail chain Debenhams and men's-wear brand Thomas Pink, in order to shed light on the inner workings of why we buy. Nightingale says that while part of our behaviour involves an awareness of what some would describe as the art of dressing, "We also have an internal influence that shapes our mood and emotions, that shapes our self-esteem and also has a cognitive function. This hasn't been very well-known until recently."

She's referring to the myriad studies that have appeared in the last five years connecting appearance to abilities and acceptance (i.e. what your shoes really say about you). If you believe them, you'd be obliged to think that people who wear high-top running shoes are standoffish, while those who favour bright, colourful sneakers are more emotionally stable. These are the results from a University of Kansas study in 2012, which examined the link between footwear and personality. While some could potentially laugh off the findings as simple, buzzy clickbait, the weightier implications can help brands market to customers better. Or, more importantly, guide us into understanding why we're being judged as books by their proverbial covers.

Unlike a removable dust jacket, however, our wardrobes can be extensive, accumulated over years and constantly acting as signifier of our inner selves. In the year I spent as a freelance stylist, I also acted as a personal shopper for several clients. When people asked me what it was like, I said I felt more like a psychologist than I did a professional dresser. I heard "I could never pull that off" more often than not, whenever a client and I spied a particularly boldly printed skirt. I always assumed this kind of sentiment stemmed from their personality alone – that they were shy and wanted to blend in.

What I didn't know is that during this thought process, another factor – "cultural inventory", as Eileen Fischer, a professor of marketing at York University's Schulich School of Business calls it – was also contributing to their apprehension. "We have this abundant set of cultural knowledge, which we may never have consciously picked up. We may have seen it in movies, where we see a character's reactions to an older woman wearing a loud dress."

These cues can also come from sources much closer to home, Nightingale points out, as something called cultural appreciation. "If your mom wore a lot of red, you would have a positive appreciation of the colour, or you'd have an appreciation related to her personality. Let's say she was determined and strong; those would be the first main appreciations you would have for someone wearing red. So if you saw someone wearing red, you would assume that they are determined and strong."

Years of cultural conditioning (rather than whether you think it would look good on you) could be the determining factor in your choice between Tory Burch’s rainbow separates (left) or Creatures of Comfort’s more neutral ensemble (right).

Years of cultural conditioning (rather than whether you think it would look good on you) could be the determining factor in your choice between Tory Burch’s rainbow separates (left) or Creatures of Comfort’s more neutral ensemble (right).

Benjamin MacDonald/The Globe and Mail

Although this culturally-derived information may lie in our subconsciouses most of the time, shopping trips are one instance in which they manifest. And the older someone is, the more it has built up. Angela Pastor, of the Toronto-based dress rental boutique Fitzroy, has experienced many occasions when customers have expressed interest in, but ultimately shied away from, an article of clothing based on an external set of influences. "We recently had a woman comment that she loved our ripped denim but could never pull it off. When we asked her why, she said 'Because I'm 40 and a mom!' We found it so sad that she loved the jeans but had decided to close herself off from that option because it didn't fit in with her idea of what a 40-year-old mom should wear," Pastor says. Fitzroy, which carries an abundance of brightly patterned and bohemian-detailed items, is very much a reflection of Pastor and her partner Julie Buczkowski Kalinowski's own eclectic taste. "We believe you should wear anything you feel good in, whatever makes you happy. We eventually convinced her to try them on and she ended up loving them and buying them."

Pastor says that since the business transitioned from retail to rental, she's noticed customers who cross their threshold are more inclined to experiment with their looks. "We've become pretty adamant about making people try stuff on that they don't think they can pull off, and so often they're surprised by how much they love it once they do have it on," Pastor says. "It makes us feel like we've done our job when we open someone's mind a little bit."

Alexis Honce, a stylist on The Marilyn Dennis Show, shares her excitement in helping clients realize that taking a fashion risk isn't as drastic, or scary, as it might seem. Yet she adds that makeovers are not a one-time investment. "It's very hard to change someone's style unless you work with them for a long period of time," she says. Shows like What Not To Wear and Ten Years Younger, Nightingale points out, don't have a high rate of continued success – that is, shortly after the makeover process ends, individuals go back to their former style – because "that is where they're psychologically and emotionally comfortable."

According to Nightingale, to truly embark on a wardrobe shake-up, a consumer must first be prepared for a careful reflection of their emotions and psyche. "It's not as simple as 'This is what I want to wear'," she says. "They also have represent a certain company, a certain social role – for example, a mother, a daughter, a wife, an executive. There needs to be an element of consistency within that." This can be achieved by an incremental shift towards change that also addresses why one wants to undertake the makeover in the first place. These questions, Nightingale says, include "Why do they want to dress this way? What are you missing in your life that you feel you need a change?"

Of course it's not always easy for someone to admit, especially to a virtual stranger like a personal shopper, why they want to overhaul their wardrobe. "I always tell them 'baby steps'", says Honce. "Maybe they should try a coloured shoe. Or, what's their favourite part of their body – maybe get a coloured pant if it's their legs."

Ultimately these gradual tweaks will ease someone into a more long-term wardrobe transition. After all, Nightingale notes, a speedy change would also cause distrust from others – a trust that's partially built by the cultural conditioning we have. Yet as we feel more at liberty to experiment with our style, perhaps even being complimented on an outfit rented while taking a risk, these cues will start to shift. And one day, the only bags we'll whisk out of a store will carry a brand new look.