Greg Bruce: Adventures in style for the sartorially challenged

The Wayfarer purchase scored points from Phil and Dean. Photo / Doug Sherring

Clothes maketh the man, or so the saying has it. Greg Bruce set himself the challenge of reinventing his style, with a little help from two friends.

Dean's beard was ginger down to his chin and then grey to his upper chest, where its magnificent voyage finally ended. He was wearing Ray-Ban Wayfarer 2132s; an untucked blue, white and yellow check flannel shirt; crisp selvedge denim jeans, pinroll-cuffed to just above the ankle; bright yellow socks and cherry Doc Martens.

He was in front of a brick wall outside his house on the coast of Kent, England, walking toward the camera, bending slightly, hands low, as if poised to do something — what exactly? It was intriguing, intoxicating, a great photograph, like something from a fashion magazine. I wanted that outfit. I wanted to look like that. I wanted to feel like that.

If anything, his picture the following day was even more inspiring. He was standing at upmarket eating and drinking establishment Searcys in London's St Pancras station. One of his feet, encased in a classic black high-top Chuck Taylor, was up on the leather banquette. One of his hands was resting on the banquette's polished wooden top and the other hand was sitting coolly on his left hip.

The picture captured the cathedral scale of the grand old station — both its former grand brick glory and its epic modern light and glass. Dean wore skinny navy chinos, cuffed to the top of his Chucks, an untucked black and red checkerboard plaid shirt, sleeves perfectly triple-rolled to just below the elbow, and the same pair of Ray-Ban Wayfarer 2132s from the day before.

The looks Phil had been sending me were fairly conservative semi-formal work outfits, but inspired or challenged by Dean's photographic brilliance, he sent a shot of what he called "My Dean": untucked red and navy buffalo check flannel shirt, sleeves rolled to just above the elbow, clean, dark navy selvedge jeans, ironworker-cuffed to mid shin, and caramel moc toe boots, It was taken in his Hong Kong apartment kitchen, but that didn't necessarily diminish it.

It's hard to say the precise point at which my intellectual and emotional life came to be dominated by fashion but I don't know that any of the roughly 130,000 beautiful, instructional, sometimes cruel words we have exchanged on our three-person Whatsapp group "Fashion" over the past two months have been as powerful as those three photos that appeared on consecutive days from June 15-17.

The three of us had become friends in our final year at journalism school. Phil had a reputation as a bad boy, at least by journalism school standards; Dean was the course's top student two years out of three. I had a wardrobe rotation of three patterned polo shirts and a single pair of jeans.

Greg Bruce, consumed by a wardrobe revamp. Photo / Doug Sherring

After J-school, as we didn't call it, we all went overseas. Never again have we all lived in the same place at the same time. For periods, sometimes long periods, up to two of us have been in touch, but in recent years our level of contact has drifted.

Two years ago, I saw Phil for the first time in years. He looked good, which was a surprise because he had always been a slob. He told me he had taught himself about fashion entirely using free online resources and had discovered how to build a wardrobe using only 16 items.

I found that idea captivating and have found myself thinking about it often since. I have spent a lifetime feeling humiliated and/or upset by my inability to dress well, starting in my high school years, when I frequently wore polar fleece tops and Sandbags-brand trackpants.

At the start of June, on a Sunday afternoon — that time of dreaming and hoping, of reassessing our lives, of imagining things other than they are — I sent Phil the following message on Whatsapp: "Can you send me your 16-garment wardrobe list so I can get buying?"

I thought it might lead to a few messages or an afternoon's discussion. Instead, it led to questions, which led to answers, then to internet links. Two weeks later Phil added Dean to a Whatsapp group called "Fashion" with a one-line instruction: "Send Greg a photo of what you're wearing" and here we are, 130,000 words later, with my wardrobe radically overhauled and my wallet $227 lighter.

The more you turn your attention to something, the more it rewards you, consumes you, and eventually defines you. What I have learned over the past two months is that this can happen with any topic, no matter how disconnected from your existing self-conception.

Sylvia Park, that grand eastern temple of ceaseless consumption, used to suck my energy so much that, after half an hour there, I could hardly summon the will to walk. Now, just the thought of visiting fills me with a sense of excitement, opportunity and personal growth. I have fallen into this so deeply I am shocked by it.

I am a systematic person, so I set about things systematically. I built a library of links to influential publications' articles about items every man needs, then I tabulated them to see what appeared most frequently.

The 10 top items were: plain T-shirts (especially white), Oxford cotton shirts (white again), V-neck jumpers, blazers, indigo/raw denim/selvedge jeans, chinos, black dress shoes, brown dress shoes, white sneakers and chukka boots.

Our 130,000 words covered big issues like black vs blue jeans, the viability of double denim and the difference between chukkas and desert boots.

I started using online services Lookastic and Epytom, which sent me daily suggested outfits. I sent some of these to the group for discussion. They sent me links to other sites and suggested other items I might buy. I started trawling online retailers. My 4-year-old daughter took daily photos of my outfits for the group's critique.

Phil and his family flew to Brisbane and back, Dean took the train to Newcastle, I went to Hawke's Bay. The WhatsApp never rested. Our 130,000 words covered big issues like black vs blue jeans, the viability of double denim and the difference between chukkas and desert boots but more surprising and insightful were the thousands of messages we exchanged about small things: when to tuck and untuck; when to pinroll-cuff and when to ironworker-cuff and when not to cuff at all; how to wear an undershirt and how many buttons to fasten over it; how many times to roll one's sleeves and to what point on the arm. Phil made me buy new laces for my dress shoes and take an online tutorial in how to bar-lace.

The whole project threatened to founder though on the fact my wife wouldn't allow me a budget, arguing that we'd already spent too much this year.

The lack of budget drove Phil crazy. One day he said, "It's difficult. You ask us what warm top you should wear but then say you can't buy it." He suggested closing down the group, but half-heartedly, I think, in the same way you tell your kids that if they don't share their toys you'll sell them on Trade Me and use the money to buy a new $250 camel overcoat from Zara.

I didn't explicitly push for budget, but clothes steadily became all I talked about, until one day, after I had been describing in detail everything I could get for under $150, Zanna, who was trying to change Casper, our 1-year old, said, "Okay, well, if it's coming in under budget that's fine."

And just like that, the multibillion-dollar world of fashion opened itself to me. Rather, it opened $150 of itself to me.

"What do you think we know about style?" I wrote to Dean and Phil. "Is there some objective thing we are pursuing? Surely it's just people agreeing about things that have no value outside that agreement."

"There is an element of rebelling against my culture and upbringing in this," Phil wrote. "Many New Zealanders respect and seem to admire understatement. They do not like any hint of ego."

Selfie time. Photo / Doug Sherring

Dean wrote: "I agree with Phil in that we grew up in a time and place where an interest in clothes was not encouraged and there were no role models. On top of that you couldn't get the stuff you wanted anyway. You'd see something in a 6-month old copy of Smash Hits and, when you realised the local Warnocks didn't stock it you'd be left trying to find the next best thing. I remember getting a friend to make me a couple of shirts and asking my grandmother to knit me a black jersey with a checkerboard hem when I was going through a two-tone ska phase. I did not look like Suggs."

"Who changed it for us?" I asked. "Who said, 'Guys it's okay to care now'?"

Dean wrote: "I remember once wearing one of my grandma's old diamante brooches to the shops during a short-lived New Romantic phase. I did this while my dad was at work."

What I think he meant was that fashion is not about getting permission. More accurately, I think he meant fashion is about not getting permission.

We got to work on the $150. I bought a white button-down at H&M for $30, black and white tees at The Warehouse for $6 and $8 respectively, a pair of slim-fit black jeans for $35 and a chambray shirt for $44 on Asos, and a bright red flannel lumberjack shirt at The Warehouse for $10. Phil sent me five new shirts. Dean sent me a five-pack of statement socks.

At Savemart New Lynn, after trying on a few ill-fitting things that smelled of old, dry skin, I found a Levi's denim jacket that appeared to have never been worn, for $15.

I put it on and sent Zanna a photo. She loved it. I sent the photo to the Whatsapp group. Phil wrote, "That is a great f***ing jacket." Dean wrote: "Jacket is fierce! You look like a ginger Paul Newman." He added three flame emojis.

And just like that, I was no longer a New Zealander who embraced understatement.

I wanted more; I had no more. There was $1.70 left. Then it hit me! I had a bunch of long-neglected, small-denomination foreign currency at the bottom of my bag. I changed it at ASB Sylvia Park. It came to $107.

Phil thought I should spend it on a bomber jacket, high-top Chucks and a tan belt. For Dean, though, the only thing that mattered was Ray-Ban Wayfarers.

They started at about $150 so I said I would get knock-offs instead. Dean attacked me. He reported a comment from his partner: "Fake Ray-Bans?! Does he want to get eye cancer?!"

I tried to find a solution. I googled "Wayfarers" repeatedly, as if that would do it. I found a site that allowed me to do a virtual try-on and frankly they looked fantastic on me.

I became obsessed, out of control. I didn't care. "I want to buy, buy, buy!" I told the group. It was unhealthy.

Dean wrote: 'Jacket is fierce! You look like a ginger Paul Newman.' He added three flame emojis.

"Get them," Dean replied supportively. "You won't regret it."

"But I only have $107," I wrote.

"They will make everything else you wear look 15-20 percent better" he wrote.

"But when I compare the pictures of the Wayfarers with the knock-offs they're basically identical. Is a couple of millimetres here or there going to make such a big difference?"

"It makes all the difference," he wrote. "Trust me. Remember it's about the small things."

"I know I know," I wrote. "But sometimes the small things appear so small and cost so much."

I found some Wayfarers on Trade Me, listed by someone from the Bay of Plenty with 100 per cent positive feedback. They looked so good. I entered the auction hot, with no intention of backing off and, after a fiery bidding war, I got them for $63. I couldn't believe it.

I sent Zanna a screenshot but she misunderstood and didn't realise I'd already bought them. She replied: "Honey, with three young children I do not think spending more than $20 on a pair of sunglasses is a good idea. Sorry, it's just too risky."

I felt bad and anxious but what could I do? I guess I should've asked for permission.

But five hours later, in England, Dean woke up and wrote: "Great call on the Ray-Bans! You won't regret it for a second. Slip them on and the world will look different … and you'll look different to it. And so what if it's a risk?" He attached a photo of Jack Nicholson wearing a pair of Wayfarers. He wrote: "Does this guy look like he's afraid of taking a risk? No he doesn't. And this is you now."

I could've punched the air. I felt the weight of years' worth of deliciously comfortable polar fleece lifting from my shoulders.

That night, Dean updated the group's icon to the picture of Jack Nicholson in the Wayfarers.

Zanna would forgive me when she saw them on me. Of that, I was hopeful.

In the days after we started what we came to call "The Project", Phil told me I had to write about it. He went on and on about what he called, "The Angle".

At various times, he wanted The Angle to be what makes something look good, or the relative conservatism of male fashion, or Dean's relative lack of commitment to The Project, or the value of technology in rekindling adult friendships, or a summary of a fortnight's outfits as curated by him.

Eventually, just to get him to stop going on about The Angle, I had to tell him there was not going to be a story. Before I did that, though, he wrote: "I think the conclusion of the story will be ambiguous and you will state the superficiality and consumerism just made you sad. You will then go home to your family and describe Casper's outfit with a line that lists the labels he is wearing, with an embedded joke about some generic baby food smeared on his shirt."

I replied: "The story will be that I came up with the perfect box of clothes for every man to look good without spending more than $1000 and here I am wearing it."

He wrote: "That's a good story. But easily found on the web."