Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
This past Sunday, I found myself completely pulled into the world of Michael Jackson and not just watching a film, but witnessing a legacy unfold frame by frame.
Going into it with an open mind, The Michael film felt intimate, reverent, and at times, hypnotic.
It captures not just the scale of his superstardom, but the story behind it.
Every movement, every glance, I found myself sitting in the theater in awe of the big screen.
Thanks to Jaafar Jackson, there's a fluidity to his performance that makes you forget you’re watching an actor at all, it was a true embodiment.
Watching him move through the eras of Michael’s life feels like watching something being created right in front of you.
From the very beginning of his career with The Jackson 5, you could already see The Jackson's approach to style was just the beginning of something great.
The looks were coordinated, colorful, and very much rooted in the 70s, but even then, there was a sense of care in how everything fit and moved.
Flared pants, tailored jackets, the polished finish, it all worked together as a band.
They helped shift the spotlight, placing Black identity and joy at the forefront of mainstream pop culture.
As he grew into his solo career, Michael Jackson’s style became a reflection of who he was becoming, not just as an artist, but as a person he was always reaching toward.
He was a true maximalist, drawn to detail, texture, and pieces that made a statement without ever losing the essence of who he was.
The glove is probably the first thing people think of.
That single, sparkling glove became such a defining part of his image.
It caught the light every time he moved and drew your eyes exactly where he wanted them.
There was something so simple about it, but it stayed with you because it was different.
It turned one small detail into something unforgettable to his wide fanbase.
His style really felt larger than life and you can see it from a mile away.
Jackets with structured shoulders, the fitted shape, the heavy embellishment.
A lot of these looks were inspired by military uniforms, but they never felt stiff.
They still allowed him to move the way he needed to on stage.
You see it in his eras like Thriller and Bad, where the jackets almost became part of the performance itself.
They carried a sense of power, but also a kind of showmanship that made them feel unique to him.
But if the military regalia was about presence, his eyewear was the one that served him protection.
His sunglasses added another layer to this carefully constructed shield.
There was a profound mystery to it; you could see him, but you could never truly perceive him.
It felt like a small, quiet way for him to hold onto something private, even while being one of the most visible people in the world.
What really stood out to me was MJ’s approach to tailoring as a whole.
Everything fits with purpose.
The lines, the shoulders were sharp, and the proportions always worked with his body, to the point you can tell his clothes were made for him, not just picked off a rack.
Even early on, he was working with dressmakers to shape how he looked on stage.
He pulled from history, art, and performance, building a wardrobe that felt almost theatrical but still precise.
In menswear, tailoring is often talked about as the difference between wearing clothes and owning them, especially in this newsletter.
Michael was a perfect example of that.
He didn’t just wear statement pieces, he made them feel natural and his impact on menswear is still here.
At the height of his career, he changed how a male pop star could present himself.
The mix of performance and precision, the balance of structure and expression, it influenced not just stage fashion but everyday style too.
When you look at everything together, the tailoring, the movement, the sparkle, it starts to feel like more than just fashion.
It truly encapsulated his unique legacy as a whole.
And I think a lot of that traces back to his childhood.
The love for fantasy, for storytelling, for those softer, more imaginative spaces that he didn’t always get to fully live in.
You can feel that in the way he held onto wonder, even at the height of his fame.
It showed up in the details, in the way things sparkled, in how every look felt a little larger than reality but never disconnected from him.
It’s what made his style feel so personal; not just iconic, but honest in its own way.
Like he was always reaching for something, and somehow bringing the rest of us with him.
His legacy continues to live on in every stage, every collection, every artist who understands that fashion is part of the performance.
He’ll always be fly at NYFG, always a reference, always a standard, may he rest in peace.
There are worse ways to spend a Sunday morning than pulling books off the shelf.
Reg and I share this particular affliction – the menswear library as both reference tool and comfort object, the kind of collection that justifies itself every time you actually need to know something, and the rest of the time simply sits there looking authoritative.
I was recently leafing through Nicky Smith's The Style of an Englishman – 1989, and showing its age in all the best ways – when I came across a page that gave me pause.
Smith lays out what she calls the basic 'basics': a travel checklist for the well-dressed man embarking on a business trip.
Three suits, six white shirts, one blazer, one trench coat, two pairs of black Oxfords, a selection of ties including, she specifies, one black silk knit.
The whole thing organised with the calm certainty of someone who knows the rules exist, that they work, and that deviation is for people who haven't thought it through.
She was right, of course. For 1989.
The world she was dressing for had fixed occasions.
Office.
Meeting.
Cocktails.
Conference.
Weekend dinner, formal or informal.
Each with its own dress code, each dress code legible to everyone in the room.
The dark navy for evening, the grey flannel for day, the cords for the informal weekend – not arbitrary choices but a system, and the system worked because everyone agreed it worked.
Thirty-seven years later, the system has not collapsed so much as dissolved at the edges.
The office is sometimes a Zoom rectangle and sometimes a co-working space in which someone is wearing a hoodie worth more than your suit.
"Smart casual" – still the most useless phrase in the English language, and showing no signs of improvement – has become the default dress code for everything from client dinners to gallery openings to occasions that simply couldn't be bothered to specify.
Trainers are acceptable almost everywhere, except the places they're not, and the line between those two categories remains invisible until you have already crossed it, in the wrong direction, in front of people whose opinion you would have preferred to keep.
The question is not whether Smith's list still holds. It doesn't, entirely.
The question is what the 2026 version looks like, built on the same logic – economy of means, maximum versatility, nothing that doesn't earn its place in the bag – updated for a world that has genuinely changed.
Here, then, is my attempt.
Two suits.
One mid-grey in tropical weight wool – the workhorse, the default, the suit that takes you from the morning meeting to the evening dinner without apology.
The weight?
Air conditioning takes care of comfort, dress accordingly.
One dark navy, cut slightly slimmer than you think you need.
The double-breasted has made a serious return; if you can carry it, this is the suit to try it in.
The third suit from Smith's list has been quietly retired.
Three suits in a carry-on is a packing fantasy for a different era.
One jacket.
Not a blazer in the 1989 sense – the brass-buttoned navy blazer belongs to a world of yacht clubs that most of us do not visit.
A soft-construction jacket in a neutral – camel, mid-brown, olive, lightweight tweed or cashmere mix – that works equally over tailored trousers and dark denim.
This is the 2026 Swiss army knife.
It goes everywhere and apologises for nothing.
Four shirts.
Two white – one formal for the suit, one slightly more relaxed for the jacket.
One pale blue Oxford cloth, button-down, which has survived everything the last four decades have thrown at it.
One fine stripe or subtle check.
Smith had six.
You don't need six.
You need four good ones and either a travel iron or the discipline to hang them in a steamy bathroom.
One of these options is more reliable than the other.
Dark denim.
One pair, darkest indigo, cut straight or very slightly tapered.
Not skinny – the moment has passed.
Not distressed – you are not twenty-two.
Dark denim with the right jacket and a proper shoe will take you further in 2026 than three pairs of odd trousers would have in 1989.
This is not a concession to casualisation.
It is an acknowledgement of reality.
One pair of flannel trousers.
Mid-grey or charcoal.
For wearing with the jacket when the denim feels insufficient, or with the grey suit jacket when you want to break it up for a second day.
Smith had the flannels and the cords.
Keep the flannels.
Lose the cords – unless you are going somewhere that cords are specifically correct, in which case you already know who you are.
Two pairs of shoes.
One black Oxford – the single constant connecting Smith's 1989 list to this one, and likely to whatever replaces it in 2037.
Beyond that, the shoe question has become genuinely complicated, and I will tell you exactly where I stand.
The leather trainer worn with a suit – a look that has achieved mainstream acceptance on the American Eastern Seaboard and certain parts of West London – is, in this writer's considered opinion, one of the sloppiest combinations in modern dressing.
It ruins both garments simultaneously: the suit loses its authority, the trainer loses whatever casual ease it was supposed to provide.
You are left with something that reads not as deliberately relaxed but as insufficiently dressed, which is an entirely different thing and considerably less forgivable.
If the occasion requires a suit, wear a proper shoe.
If it doesn't require a suit, don't wear one.
The leather trainer is not a bridge between these two positions. It is a hole in the middle of the bridge.
For occasions where the dress code is genuinely ambiguous – and 2026 provides these in abundance – the answer is not a cleaner trainer.
It is a better shoe.
A tasselled loafer in cognac leather or suede reads as considered rather than casual.
The Belgian loafer, for those who know them, operates in the same register – effortless, if you have the insouciance to wear them with or without socks.
Or, for something with genuine transatlantic authority, the Bass Weejun in cordovan: an American staple crossing the boundary between formal and casual with aplomb since 1936, and showing no sign of stopping.
Any of these three will take you places the leather trainer cannot, worn with things the leather trainer should not be near.
One knitwear anchor.
Smith's four-ply cashmere V-neck in cream remains correct and you should own one.
Add a lightweight merino crewneck in navy or mid-grey – thin enough to layer under a jacket, substantial enough to wear alone, light enough to drape over one’s shoulder, should the mood take you.
Between these two you have covered every temperature differential a modern hotel will throw at you.
One coat.
The trench coat survives intact.
It is one of the few garments that has never needed updating because it was correct from the beginning.
If you don't own one, buy one.
If yours is showing its age, have it cleaned and pressed within an inch of its life – which is, in itself, a kind of elegance.
A well-maintained Barbour, as an alternative, covers suit, denim and everything between.
This is a very personal choice, and you know if it's yours.
Ties.
Optional – a word that would have been unthinkable in 1989.
Bring one: the black silk knit Smith specified, still the most versatile piece of neckwear ever devised.
I have written at some length about the tie and its proper uses (Ties That Know Their Place, February 2026) and will not repeat myself, except to say that the man who knows when to wear one and when not to is more interesting than either the man who always does or the man who never does.
On cufflinks – and it is a question, despite what certain corners of the internet would have you believe – I have expressed a view (Cufflinks? Seriously?, March 2026) that need not be restated.
The short version: they matter, the right ones reward attention, and the wrong ones undo everything the shirt was trying to achieve.
One addition Smith didn't include, because in 1989 she didn't need to.
A good linen handkerchief.
Two, if you have room.
White, plain, folded simply into the top pocket.
Not silk attempting to be decorative.
Not a printed affair announcing its own presence.
Linen – which washes easily, travels without complaint, and has the particular quality of looking better slightly worn than fresh from the packet.
The pocket square has become sufficiently optional in 2026 that its presence is now genuinely noticed.
This is an argument for wearing one, not against it.
The additions Smith couldn't have anticipated.
Well-cut chinos, dark or khaki – occupying the space between tailored and casual that 1989 didn't quite have a name for.
A plain white or navy T-shirt in quality cotton, for under the knitwear, for the hotel gym, for the Sunday morning when you're not seeing anyone who matters.
A belt – one, in dark tan or cognac leather, for everything except the black Oxfords, for which you need a black belt.
Yes, you need both.
The logic is the same as Smith's.
Everything earns its place. Everything works with everything else.
The number of pieces has barely changed.
What has changed is the occasion they're dressing for – less fixed, less legible, but not, if you know what you're doing, any harder to navigate.
Smith got it right in 1989.
The basics are still the basics.
They've just learned to travel lighter.
Do You Need My Help?
Have you ever found yourself staring at the closet not knowing what to wear?
Do you need help with coordinating pieces?
Do you constantly struggle putting an outfit together and want to turn that confusion into confidence?
Then let's talk about how we can improve your look.
Just by making simple fashion decisions, you can boost your self-esteem, make you more productive and improve your career opportunities. Every week, I help 1,000+ men make the most of their wardrobe with fashion tips to upgrade your life.
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