Fashionable Villains

The Krays were hot to trot. Al Capone – epitome of the roaring 20s, even the cigar smokin’, gun toting Bonnie and Clyde had a certain style.  

There’s something that separates your run of the mill criminal from the big names.  We think it’s got something to do with their choice of clothes and shoes.  

Here we take look at dress sense – hoodlum style.  

Al Capone

Al Capone

Al Capone
Source: Wikimedia Commons

In public, Al Capone was immaculate; the fedora, the tailored pinstripe suits and spectator brogues were sheer class. In private, he was a prohibition era bootlegger, pimp and extortionist. In his own words, he was, “a businessman, giving the people what they want.”

Three deep knife wounds to his left cheek earned him the nickname, Scarface, but despite his looks, Capone was a celebrity. Thanks to his legendary generosity, the eponymous crook was widely viewed as the Robin Hood of 1920s Chicago.  

But in 1929, at the peak of his notoriety Capone’s reputation took a broadside. Seven members of Bugs Moran’s rival north side gang were gunned down in a garage and Al was blamed.  The St Valentine’s day massacre, proved to be the beginning of the end for Capone.

Law enforcers began to take a serious interest in his business affairs and on 17th October, 1931, Al Capone – the snappy dressing crime boss – was sent down for 11 years for tax evasion.   

Bonnie and Clyde

bonnie and clyde

Bonnie and Clyde
Source: Wikimedia Commons

Young, wild and indulging in extramarital sex.  It may sound like your average 18 – 30 holiday to our modern ears, but in the America of the great depression, such high jinks were the stuff of newspaper headlines. Add some photos of a glamourous couple, armed to the teeth and smoking cigars as they pose before their stolen car, and you’ve got a legend in the making.

Bonnie in her long figure hugging dresses, and Clyde in dapper suits and open neck shirts; at a time when millions were living at or below the poverty line, theirs was a story that fired the imagination of the tired and dispossessed.

But while they looked like they were having the time of their lives, reality was rather different.  Bonnie had been bored and dissatisfied with her life as a waitress.  Clyde was a petty crook before a spell in the pen that saw him, according to a fellow inmate,  “change from a schoolboy to a rattlesnake.”

From the get go, their rampage was a desperate, doomed affair and both Bonnie and Clyde knew it.  Finally ambushed on a desolate road in Louisiana, they were both died as they had lived – riddled by bullets. Bonnie’s fancy clothes were stolen and auctioned off by a light fingered bystander.


Reggie Kray

Reggie Kray and friends
Source: The National Archives UK

“They were the best years of our lives. They called them the swinging sixties. The Beatles and the Rolling Stones were rulers of pop music, Carnaby Street ruled the fashion world… and me and my brother ruled London. We were f****** untouchable…” –  a quote from Ronnie Kray’s, autobiography.

Ronnie and Reggie Kray, hid in plain sight.  At their zenith, the twins, wore razor sharp Savile Row suits and mixed with rock stars, MPs and the aristocracy. Their chain of nightclubs and scrap metal dealerships, masked their true identity. Vicious criminals, they ran protection rackets and dealt in robbery, hijacking and arson.

Murder was nothing to these men.  In 1966, Reggie shot and killed criminal rival, George Cornell, in the Blind Beggar pub in Whitechapel, sparking a crime war.

Worse was to come, when the following year, the twins decided to wreak vengeance on one of their own for failing to fulfill a contract.  Jack ‘the Hat’ McVitie is alleged to have been stabbed so many times by Reggie that his liver fell out and was later flushed down the toilet.

They may have worn the smartest Oxfords, but their soles were steeped in blood.  McVitie’s body was never recovered, but the Krays were eventually jailed for the murders; their sentence 30 years without parole.

Frank Lucas

Frank Lucas

Frank Lucas
Source: Wikimedia Commons

Wearing a knee length chinchilla coat with matching fedora today, would incite crowds of animal rights aware citizens to riot.  But back in the 1970s, Frank Lucas was a big time drugs baron.  He could wear what he liked – and you’d better like it.

Lucas, it has to be said, was more usually to be seen sporting a very well cut, but inconspicuous suit – his wardrobe paid for by drug smuggling on an unprecedented scale.  The dude from Harlem made it big by breaking the Mafia stranglehold on the New York drug trade.

He travelled to South East Asia where a family connection helped him set up an import business. Vast quantities of exceptionally pure heroin were smuggled into America, it’s claimed, in the caskets of dead soldiers being returned from Vietnam.

In his heyday, Lucas had tens of millions of dollars stashed in accounts in the Caymen Islands and owned property all over the United States, including a cattle ranch in North Carolina.  He’s reported to have lost the lot after he was finally busted in 1976, but Lucas, who turned 83 this week is still a pretty snappy dresser, so who knows..

Men’s fashion blogs straight off the hanger

We recently listed some of our favourite blogs, and since then we’ve found some more.

So here, for your pleasure, are some of the best men’s fashion blog that the web has to offer.

Boy Meets Fashion

Jaime Jan Boy meets fashion

Not your average boy.
Not your average blog.

If you wrote a blog, would you feature a lady you met on the morning commute? Say hello to a blogger, Jamie.

This London boy ranks eighth in the Telegraph’s “Top Fifty Fashion Insiders”, and loves everything to do with fashion. Here you’ll find info on shopping apps, the “bad boy nerd” look, and even posts on ladies’ shoes.

Want the lowdown on the denim section at Selfridges? Find out about the £11 bargain Jamie found there – or the diamond studded jeans. How much do you think those cost?


Bob Larking of Chivalrous

A gentleman, and a scholar.
And also a blogger

There is nothing wrong with the colour pink. And that’s clear from Bob Larking’s John Lennon inspired blog post.

While Larking may use Arthurian legends as lessons on how to behave, he isn’t a chainmail wearing brute. This philosophy graduate swaps shields for shirts and swords for poetry on his way to creating “hybrid looks”.

A blogger with style, and thanks to a Ted Baker contest, one with cufflinks, a designer pocket square and some dashing stripy socks.

Lads Style

Lads Style NYC

For the lads.
By the lads.

The word, “lad” is often synonymous with wild hooting, mindless “banter” and very ungentlemanly behaviour. But don’t worry.

Founded in 2012, Lads Style has sought to become the style HQ for “proper blokes”. They also prove that beige, when worn with blue, is a fantastic colour combination.

This recession busting, affordable clothes loving blog, is run by lads, for lads, without the aforementioned negative vibes. And there isn’t a £300 motorbike jacket in sight.

Omiri and a Dream

Omiri Thomas on a curb

What’s in the bag?
A dreamy blog post?

Have you ever been stopped in the park and asked to put a green acrylic box on your head? Well blogger, Omiri Thomas has.

After hearing “Where did you get that from?” for the “umpteenth” time, Omiri Thomas began his fashion blog. Now this hat wearing fan of style classics, wants to share his Great Gatsby inspired look.

The London Collections posts feature three very different outfits, and tell of a chance meeting with David Gandy.

Rogues and Brogues

Ian Megrath trilby

Another hat wearer?
It must be fashionable.

Grab your weapon of choice when fighting the stubble, and when growing a beard, “don’t force it.”

Away from posts on facial fluff, this is the fashion blog of Ian Megrath, who in his own words is a “30-something who dresses like a 20-something on the budget of a teenager”.

With his teensy budget, Ian can’t afford to be picky, But he certainly knows how to get the most from a cash strapped wardrobe. This isn’t about high end fashion; it’s a blog for the “Everyman”.

St James Style

St James Style Blazer

Be lazy. Or break the rules.
Don’t do both.

Don’t look like a schoolboy. Don’t wear a short sleeve shirt. And in case you didn’t know Panama hats are a better option that baseball caps. That’s the St James Style.

Blogger, Jake, writes about his experience of buying a bespoke suit. With autumn nearly upon us, he opted for wool, but do also check out his post on summer suits – lightweight fabrics for dealing with the sizzling sun.

The Rakish Gent

Rakish Gent Taj hayer

Rakish Gent.
Taj Hayer

Are you a gent with suave dance moves and smoothly rehearsed pick up lines? Well you’ve come to the right place.

Hayer’s bid to help men become more debonair includes an interview with the mustachioed stylist, Franco Vallelonga. In Franco’s eyes a rakish gent is a man who “has made a conscious effort, but looks effortless.”

Hayer writes posts on shopping trips, brand profiles and style icons, creating a jaunty ride through the fashion world.

The Student Tailor

Student Tailor

Wakey wakey.
Rise and shine.

If you’re a morning zombie, take a look at Aleksander Cvetkovic’s morning routine. This Oxford student will teach you how spending that little bit of time choosing an outfit, can really improve your day.

Ever wondered what colours make a good mix? Or do you need help picking the correct cloth? Learn about Aleksander’s love for gentleman’s outfitting, and find answers.

This blog is young, and so is its author. But while Cvetkovic may only be twenty, he has a wealth of fashion knowledge with Jazz being a particularly strong influence.

The Style Derektory

Linen suit and blue shirt

Look up stylish.
In the Style Derektory.

With help from family, Derek proves you can stay stylish over sixty. His Joan Rivers-esque critiques and warnings of crimes against fashion are sandwiched between picnics at Lords and the odd comedy text message.

Just what is an “international style chameleon”? Well if you’re unsure what that means, then Derek will clear it up.

It was after his daughters mooted the idea, that North Londoner Derek began his journey into outfit centric fashion blogging. He has a style for all occasions, and can even be seen in the egg and bacon of the MCC.

Top Grain

top grain header cropped

Top Grain.
Top blog.

Find the garment that matches your wallet with the “Good, Better and Best” section, where Matthew Coles selects three products from different price brackets.

If you aren’t happy with cargo trousers for £19 then Matthew’s pair for £415 might foot the bill.

But it’s not all high end and high price. Because though Mathew visits Florence for fashion show, Pitti Uomu, he’s also on hand to advise you on how to button your blazer.

The psychology of men’s shoes

Before we build relationships, we have to make a first impression. So often the look of the person and the clothes they wear are the driving force behind this meeting moment, but what about the shoes?

There are many theories on what different shoes for men represent, but a University of Kansas study reveals some startling results. Whether it’s Chelsea boots or penny loafers, what you wear on your feet may well dictate how other people perceive you.

Oxfords: solid guy

Black Oxford shoe

The classic, solid Oxford shoe

A man with immaculately presentable shoes, may seem like a catch, but he might not reciprocate an emotional attachment. According to the study, those who have fantastically shiny shoes, may be more attached to their footwear than friends, family or a possible partner.

So if a man is dressed in a wonderfully shiny pair of Oxfords, does that mean he is exuding messages of short-termism?

Though the gentleman in question may have attachment anxiety, it may be that he’ll apply his conscientious approach to footwear, to the rest of his life. The same shiny shoes that are the mark of a social shyness, might also be a sign of dependability. In short – shiny shoes – solid guy.

Good time Gibsons

Brown lightweight Derby shoes

Is it a Derby or is it a Gibson?

A man in unkempt trainers, or unshined Gibsons, may seem like a lazy so and so, but research suggests the wearer is socially energetic.

Wearing well worn, slightly shabby looking shoes, is a sign that the gent in question doesn’t have time to buff his boots or go shopping for replacements. Wining, dining and having a good time top his list of priorities, and he is very good at them too.

Chelsea boots: colourful characters

Samuel Windsor boot collection

Which boot would you wear?

It seems obvious, but the bolder and more colourful the shoe, the more extrovert the character wearing them.

But it goes a bit deeper. While someone who picks big, bright boots may be confident, it also appears those more partial to colourful shoes are more open to conversation and are good at public interaction.

Chelsea boots are the footwear choice of ‘entertainers’, but at the same time, a colourful shoe wearer makes a better friend.

These shoes have a point

Their shoes may be the envy of many, with style oozing from the seams, but according to the study, those wearing the most stylish shoes, were also the meanest. And those who had the most visible brand name, were the worst of the lot.

Pointy shoes look great but they can be pretty uncomfortable. According to the study, sharp toe caps give the first impression that the man wearing them is more concerned with personal aesthetics, than inner happiness.

To say that all stylish men are mean hearted, is a wide sweeping statement. Take time to chat. Check that the man in question is comfy in his shoes, before making up your mind. A sartorially elegant man can be likeable too.

Style costs

Fashion doesn’t always come cheap, but researchers did show that the more expensive the shoes, the more stylish people considered them to be.

But be warned that flashing the cash, doesn’t necessarily make a man more likeable. The more money, spent, the more stylish shoes become. But in terms of first impressions – the more you spend, the more shallow people think you are.

It’s certainly possible to look stylish and be a nice fellow, but perhaps what this proves is that money can’t buy you happiness.