Illustration by Rachel Ann Lindsay       

A day with a personal stylist teaches our writer some hard lessons: every woman needs a great bra, red only looks good on certain people, and you should never shop with your best friend.

It’s Friday afternoon, and there’s a glamazon on my front porch. Massive Gucci sunglasses shield most of the upper half of her face. Dainty silver sneakers match a slouchy silver bag slung over her arm which, along with her other arm and torso, is clad in a black wool coat that somehow manages to be the height of chic even with ruffles at the wrist and around the collar.

I’m about to invite this woman into my home to critique my wardrobe — and by extension my taste — and, for a split second, I consider grabbing my sweatpants and running for cover. But she pushes the sunnies onto her forehead and smiles, so I relent and invite Kelly Millar, my new stylist, upstairs for a cup of tea and a thorough wardrobe renovation.

“My clients aren’t unfashionable,” Kelly reassures me as I nervously fuss over the tea tray, “They are mostly busy, professional people who need a bit of help with their wardrobe. I mean, at some level everyone cares what they look like.”

Care? I certainly do, though I never thought I’d be soliciting help from a total stranger. But after a recent career shift it became clear that my professional wardrobe needed serious attention.

Though I’ve never been a style disaster, the mere thought of weeding through my jumble of jeans, tees, and hastily purchased skirts gave me the sweats. Pride stopped me from asking a friend to help out, so I enlisted Kelly, 35, whose resume spans fashion, photography, journalism, and a laundry list of stints in international capitals.

Personal stylists, or “image consultants” as they’re often known, eschew the idea of change, offering instead the seductive promise of upgrade. Like flight attendants handing out business-class boarding passes, stylists present their clients with a ticket to a hipper, cooler version of themselves. If all goes according to plan, in four hours I’ll be Claire 2.0.

“Stand over there and take your cardigan off,” Kelly tells me, and the critique begins.  First things first: a quick physical once-over. “You’re petite,” she murmurs, “and busty. I bet you have a hard time finding blouses that fit. Have you gone for a bra fitting lately? I can’t tell you how important it is to have a bra that fits properly. I’ll give you the name of a place.”

I cringe, turn sideways, and she continues. “You don’t carry your weight on your hips. If you gain weight it’s at your waist.” I wince. “And your upper torso.”

The back of my neck is starting to flush and my breathing gets a little shallow. Not since teenage ballet class has anyone surveyed my clothed body with such a critical and honest eye.

Body size and shape assessed, we move on to what I’ve been dreading: the Wardrobe Advisory. Wanting to get my own personal version of “What Not to Wear” over with as quickly as possible, I hurriedly pull on a few business outfits and send a quick prayer of thanks to the deity who refrained from installing 360-degree mirrors in my apartment.

Surprisingly, my choices mostly meet with Kelly’s approval. I get the go-ahead for pencil skirts, trouser or boot cut pants, scoop-neck knits, and a black sheath dress. She’s less excited about skinny jeans, turtlenecks, and a puffy-sleeved red top but stops short of carrying them downstairs to the dumpster.

As we weed through my closet, Kelly explains that at its base, style is about finding and sticking to a flattering silhouette and wearing the right colours and patterns. I make a pile of the clothes that fit into my newly identified silhouette and realize that they are my favourites anyway. Kelly smiles knowingly.

Colour can be complicated. Far more than the cut of a blazer, the colours we choose to wear send distinct messages about our personalities and preferences. Just ask any guy what he thinks about wearing a pink dress shirt. But personal colour palettes are based on a person’s eye, hair, and skin tones and may have nothing in common with an individual’s colour preferences.

After I proudly show off my sixth favourite black sweater, Kelly stops me. “No more black,” she decrees. “You should think about chocolate brown or grey, even navy blue. And soft colours — pastels or light purple.”

I’m unconvinced: pastels conjure images of grannies and prep school girls. But there’s no time to complain; we’re heading out the door to replace my recently culled garments.