Dressing the part

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

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.

With about 40 clients ranging in age from their mid-twenties to their sixties, Kelly’s professional shopping trips vary widely in budget and scope. “I just had a client last week, just turned 30, and she’s just really starting her career,” she says. “She basically had $1,300 — but I think we pushed it to $1,500 — and we actually did a lot, hitting mid-range stores for that.

“$1,200 is the low end, but it really depends whether it is a wardrobe overhaul or if I am just adding a few fresh pieces for the season. Once people are a little more established, in their mid- to late-30s, people will say ‘Right, okay, fall shopping time, I need to get my wardrobe in order.’ They’ll have budgets from $2,000 and up, and that’s really realistic.”

Clients pay for the clothes as well as paying Kelly for her time, maxing out at $950 for an eight-hour day, so the entire experience is not for the threadbare of pocket. But shopping with her is a combination of your cool older cousin (the one taught you how to walk in her high heels and whose boyfriend just might have a motorcycle), your practical home-ec teacher who notices wiggly seams and cheap fibre blends, and a bodyguard named Hank.

As we enter the first shop — Josef, Jacob’s upscale brother — Kelly lays down the law: “You have to try on whatever I tell you to, even if you hate it.” She also has veto power over any of my picks.

I follow Kelly around trying to absorb or scribble down her cheerful running commentary. “You don’t want things to look cheap, so it’s about being creative and finding the main pieces to look good that are decent quality — like suiting, a nice jacket.” She holds up a charcoal blazer, considers it, and hands it to the waiting salesgirl. “That’s where you want to pull the quality in and then maybe the underpinnings, that’s where we go budget.”

So should we start with a quick trip to La Senza for some better fitting underpinnings? Kelly fixes me with a withering gaze; underpinnings are clearly not the same as undergarments. “No,” she sighs as though explaining to a small child, “You are going to have to spend $150, maybe $125 on a bra. It will make a huge difference in how your clothes fit. But you probably need an afternoon for that.”

Two hours of whirlwind shopping and my head is swimming with advice and I’m pretty sure I live in a change room. The shopping bags over Kelly’s arm (yes, she does carry the spoils) contain skirts, a suit, some blouses, a pair of earrings and a necklace, and one cloche hat. I’ve long since given up calculating my credit card balance, and there are plans to swing by Club Monaco tomorrow to fetch a couple of pairs of trousers.

When I mention it’s a bit like shopping with my best friend, Kelly corrects me: shopping with a friend can be hazardous. Female competition is a powerful thing, and your friend may not always have your best fashion interests at heart. Although the brutal honesty is hard to take, Kelly is militantly on my side, effectively defending against pushy salespeople and my desire to buy even more black sweaters.

“There are the general guides to what’s hip, what’s useful,” Kelly reminds me. “But at the same time, that doesn’t work for everyone and everyone’s body type. It’s about self-empowerment.”

And I am empowered. Sort of.

In the week following my wardrobe blitzkrieg I go on my very first business trip. Packing is a snap: I now have outfits. My stylish boss compliments me on my attire two days in a row. A friend wants to know where I got my necklace and my boyfriend strongly approves of the pencil skirts.

But Claire 2.0 is still in beta. I crave a bright red coat, but the desire seems illicit. Wearing Kelly-approved clothes feels like playing dress-up and the compliments are making me wonder what a walking disaster I was pre-Kelly.

So was it worth the ego searing and credit card melting? It pains my thrifty Scottish soul to admit it, but the overall effect of my stylist was positive. When I get dressed in the morning, I am far more confident of my choices and my wardrobe now matches my profile as an upwardly mobile young professional. Yet in the spirit of the looming recession I didn’t take all of Kelly’s advice: a $200 cashmere cardi? The $20 Zara cotton version looks just as good.

Illustration by Rachel Ann Lindsay