I once went to a house party in the Cotswolds where the owner of the estate (who I’ll call Henry) greeted us guests wearing a shirt so frayed down the collar you half expected it to fully disintegrate at any moment. He was wearing trousers with signs of wear on the knees, and a barely perceptible patch down near the rear pocket. He wore shoes so old and brown that they’d been polished to a perfect patina; the shine so strong you knew they’d been resoled at least twice.
He very easily could have passed for slightly scruffy—perhaps even down on his luck—if it weren’t for one key detail: those trousers were bespoke from Anderson & Sheppard. That shirt was handmade Turnbull & Asser, likely around ten years old. And those shoes were Edward Green, probably older than everyone else at the party put together.
Henry, meanwhile, was worth tens of millions of pounds. He also owned the house we were currently standing in. <img class=”alignnone size-full wp-image-2193″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_Assared_menswear_sksMarch2015.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most Assared menswear (sksMarch2015)” width=”640″ height=”426″ /> Welcome to the wonderful world of “comfortably posh” dressing, which could arguably be considered Britain’s most understated, complex, and aspirational style of dressing for men.
Clothing that screams privilege while somehow appearing not to care about appearances at all.
Clothing that whispers rather than shouts, ages instead of dates, and prizes heritage over hype. It’s a look that requires immense confidence and knowledge to pull off correctly, despite being constructed on top layers of relaxed nonchalance. <img class=”alignnone size-full wp-image-2194″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_Btifound_menswear_trimmed_1.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most Btifound menswear (trimmed)” width=”640″ height=”426″ />What makes this style so inherently British is that it somehow combines elements of wealth and privilege with deliberate signs of wear. In no other country would the billionaire runoff invest in clothing that looks borderline homeless.
Italian high society will express their wealth through expertly tailored suits and handmade shoes sewn with sprezzatura. America’s old money likes to dress in polished preppy staples. The French traditionally favour luxuriously understated clothing with razor sharp tailoring.
But up here in the UK? Meet Britain’s mega-rich, proudly wearing jumpers with holes moth ate in them and thirty-year-old tweed jackets with sweet packet wrappers permanently ingrained in the pockets. For years now I’ve been studying (& scandalising) members of this crowd (mostly for editorial reasons, I promise), so I’ve decided to compile what you might call “a field guide” to dressing like you could effortlessly wander around WORS in a heritage shirt that you’ve had longer than most of your readers have been alive.
Learn these rules like etiquette, then forget about them all together just as you’ve started to master them. <img class=”alignnone size-full wp-image-2196″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_Edwin_T._Johnson1.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most Edwin T. Johnson” width=”640″ height=”426″ /> Rule No. 1: Clothes should never look new.
Save for trainers and certain casual wear, “new-looking” is a sin. That bright, untouched-from-box shine on suits, shirts, and footwear is slightly vulgar. Even your woodland wear should look like it’s been slept in, thrown over branches, and battered around in hilltop storms for years.
Green wellies should be caked in mud from at least three different seasons. Tweed jackets should have at least ten years of life lived into them before they hug your body the way they should. Formalwear should look like it’s been handed down from your grandfather (ideally, it has been).
To ensure clothes never look new, they have to be exceptionally high quality. Which brings us to Rule No. 2. <img class=”alignnone size-full wp-image-2195″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_CGettyImages698615702.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most CGetty Images 698615702″ width=”640″ height=”426″ /> Rule No.
2: Only buy from certain brands. Or, more specifically, only buy from an extremely short list of brands that doesn’t really change from generation to generation. For country clothing that’s Cordings, Purdey, Farlows.
For tailoring, it’s old Savile Row stalwarts like Huntsman, Anderson & Sheppard, Henry Poole. Shirts are Turnbull & Asser, Hilditch & Key, New & Lingwood. Shoes are Crockett & Jones, Edward Green, Tricker’s or John Lobb.
To anyone else, these subtle differences in cut and detail might not be obvious, and that’s kind of the point: there are no tell-tale brand names, no logos, no flashy design cues that give the game away. But to those who know, they’re written all over your fitted cotton shirt. <img class=”alignnone size-full wp-image-2197″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_JamesArmstrong1989.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most JamesArmstrong1989″ width=”640″ height=”426″ />Rule No. 3: Said brands should mostly be bought secondhand.
The right country clothes are handed down from fathers to sons. Failing that, vintage shopping at places like Apples or PorterBay is just as acceptable, so long as you know where to look. I was once involved in a full-blown argument between two otherwise genteel men as to whether a tweed jacket belonged to someone’s father or uncle.
The fact that someone clearly did, mattered more than who. <img class=”alignnone size-full wp-image-2198″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_(1).jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most (1)” width=”640″ height=”426″ /> Rule No. 4: Wear a handful of garments that you’ve been told to wear since birth. There’s nothing remotely fashionable about the comfortably-portioned-shirt-and-navy-blue-slim-trousers combo that pretty much every gentleman from these elite spheres owns.
Country-wise? Think well worn Barbour jacket (the Beaufort or Border model, patched at least twice rather than just replaced), corduroys or moleskins in earthy browns and greens, classic tattersall cheque shirts, and those infamous ancient brown brogues or equally vintage deerstalker boots. You knit will likely be lambswool or cashmere, usually in that iconic diamond-pattern Fair Isle design, or more simply in bottle green, navy or burgundy crew necks.
For urban wear? Classic British tailoring in slim but not skin tight cuts, usually boasting regimental badges, school ties, or membership of certain clubs you’ve probably never heard of. White and blue shirts galore, with the occasional plain stripe or cheque shirt thrown in for “fun”.
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Accessories are kept to a minimum, but may include a family signet ring (God forbid it be trendy), a discreet Jaeger-LeCoultre or Patek Philippe mechanical watch worn on a leather strap (never the gold cuff type), and maybe even a pocket square (but not casually folded, mind. It should look like it was shoved in there). <img class=”alignnone size-full wp-image-2199″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_(2).jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most (2)” width=”640″ height=”426″ /> Rule No. 5: Look a little messy.
Except your shoes. Those must always be polished. While your tailoring may be from the 1950s, it will also have been brushed, hung up respectfully after wear, and maintained proudly.
Your hair may look like you throw it up yourself five minutes before leaving the house, but I can assure you it’ll have been cut by the best barber in town (who has probably been cutting hair for your family for generations. “My Dad took me to get my first haircut at Trumper’s. His Dad took him…”). Yes, these elders of elite dressing have mastered the art of looking effortlessly messy.
Tops popping out of trousers, rolled up jacket sleeves, loose knitwear hanging off shoulders. It creates an illusion that, yes, they care what they look like, but not enough for it to actually matter. It’s a deeply British notion that’s built entirely on privilege. <img class=”alignnone size-full wp-image-2200″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_mossa.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains mossa” width=”640″ height=”426″ /> And that, dear readers, is what makes it impossible to replicate.
Time can’t be bought. You can invest in a Barbour jacket that once belonged to Harry Palmerson, but unless you’ve spent years trudging through mud on it and patching it up when necessary, it’ll look like brand new. You can have your suit bespoke from Huntsman, but if you wear the piss out of it in the next five years rather than carefully maintaining it for fifty, it’ll still look worn.
You can maybe buy a vintage Alec Gordon jumper from Portobello market, but you’ll never know how many pies it’s actually been worn eating before you buy it. Of course, there’s also the factor of ease. Someone who’s wealthy enough to buy from these brands will always appear to wear their clothes better.
They have the leisure time required to pick up these lifestyle-based signifiers. When The Duke of Edinburgh regularly attended events wearing suits that were several decades old, he wasn’t doing it to save money. He could have bought new suits every day of the week if he wanted.
He wore those suits for decades because he didn’t need to prove himself with fashion or clothing. It was the ultimate flex of privilege. <img class=”alignnone size-full wp-image-2201″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britain.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britain” width=”640″ height=”426″ /> Yet here’s the thing I love most about this style: it communicates values. Worn correctly, it says you value continuity over consumption.
Tradition and inheritance over abundance. It implies you’re comfortable inheriting things both materially and culturally. It doesn’t brag, yet loudly announces that the wearer prefers things that improve with age and wear (denim jeans, obviously being one of the prime examples).
At a time where we’re encouraged to throw clothes away after a handful of wears, there’s something quietly revolutionary about dressing in items that’ll last you a lifetime… or longer. If you’re interested in dressing like a comfortably-wealthy Englishman without actually being comfortably-wealthy and English, then my advice is to pick up on the ideology rather than the items themselves. Invest in clothes that will get better with age.
Build relationships with craftspeople who can tailor, repair, and resole your clothes so they’ll last decades. Try to love patina and wear as much as you hate stains and damage. And for fuck’s sake, don’t try.
This is a marathon, not a sprint. Lets address the elephant in the room. A lot about “comfortably posh dressing” is undeniably elitist.
The items listed throughout this feature aren’t accessible to most readers. The ability to take decades to pick up on life’s subtle nuances is a privilege not afforded to everyone. Let’s not pretend that referring to this style invokes anything other than British class.
Which is fair enough.
But what if we took the core idea—that our clothes should last us a lifetime; that we should value quality over fleeting fashion; that mending is better than buying new—and ran with it? What if we could adopt the ideology without the inherited bank accounts and ancient family estates?
I’ve watched men wear the same dinner jacket to the same events every year for thirty years, getting it let out and taken in as their stomachs expand and contract with age. I’ve seen them instinctively reach for shoes they know can be resoled and repaired rather than contemplating the unnaturallycheap-onese they really want. I’ve cried watching one guy destroy his favourite jacket by accidentally washing it, only for him to cry because he couldn’t bear to buy a new one.
This isn’t sustainable fashion, this is a mindset born out of a time before we could buy new clothes every week. <img class=”alignnone size-full wp-image-2202″ src=”http://sartorialhim. co.uk/wp-content/uploads/2015/04/im1979_The_Art_of_Looking_Comfortably_Posh_-_Britains_most_balbesung.jpg” alt=”im1979_The Art of Looking Comfortably Posh – Britains most balbesung” width=”640″ height=”426″ />Part of me hates “comfortably posh dressing” because it is wholly exclusive. But another part thinks we could all learn a thing or two from dressing how you’re meant to in 50, 60, 70 years time. The comfortably off give us heritage menswear.
They taught us that buying better things we’ll love for years means we buy less. They taught us that visible mends are cooler than letting your clothes autumn apart. They showed us that, with the right items, we could look better in thirty years than we do now.
They showed us that some things—clothes, ideally—get better with age.
