Picture pinstripes and you probably imagine them wrapped around a braying financier, with a phone cradled against each ear and a lady of negotiable affection perched on his lap.
The pattern’s been the unofficial uniform of bankers since the 1980s, serving as silver screen shorthand for avarice and sociopathy in Wall Street, American Psycho and The Wolf of Wall Street. Tony Montana even met his end in a chalkstripe three-piece.
British bankers birthed the style in the 19th century, though back then they were more interested in blending in than standing out. Banks each had their own stripe, varying in shade and weight, that identified who worked for which.
But after they were adopted by the Chicago Cubs baseball team in 1907, then stolen (and made more famous) by their rivals, the New York Yankees, they took on a more maverick air.
The Brits had worn pinstripes only on their trousers, but in the US, gangsters went for whole suits, a boldly patterned middle finger to the pursuing, funereal feds. Movie stars like Clark Gable, eager to cultivate an outlaw aesthetic, followed suit.
Pinstripes were worn by glamorous, womanising men. Then suddenly, by anyone who wanted to be considered glamorous and womanising, even if they worked in insurance. The elan went and pinstripes became try-hard plumage.
In other words, they were perfect for finance’s alpha male bastions of bad taste, who adopted them in the 1980s as a sartorial dick swing, amplified by a double-breast cut and scarlet braces. For anyone who didn’t judge someone’s worth only by the size of their pay package, they were too gauche for words.
The Crash And Recovery
Until 2008, that is, when the bankers destroyed everyone else’s life savings and demand for power suits collapsed as quickly as Lehman Brothers. No one wanted an outfit that telegraphed your responsibility for the worst financial crisis in living memory.
That made pinstripes ripe of reinvention. In the decade since, designers have tossed out traditional tailoring and treated pinstripes like any other pattern. They’ve appeared on everything from overcoats to T-shirts and had a particular boom in the #menswear days, when Pitti’s peacocks took them in a louche, deconstructed direction.
As moods have shifted, you’re more likely to find today’s pinstripes on a pair of cord-tied joggers than anything with shoulder padding. “They’re a modern take on a classic, worn in a hybrid way,” says Topman buying director, Rachel Morgans. “These days you can wear a pinstripe trouser with a casual T-shirt and trainers.”
Not that the pinstriped suit is dead, it’s just different. “It’s down to the cut and colour combinations. The finer details,” says Alexander McCalla, stylist at Thread. “If you change the fit, break it up or wear it with trainers, it can look interesting.” The banker suits were defined by hypermasculinity: strong shoulders, an exaggerated chest and narrow waist. So just do the opposite. “Dress it down. Try an unstructured, Italian-style jacket with a soft shoulder.”
That said, there are some men who should avoid pinstripes entirely. All that up-down movement means beanpoles look even longer, although shorter guys can use that effect to their advantage. “Narrower pinstripes makes you look taller,” says McCalla. “If they’re further apart, like with a chalkstripe, you look wider.” LeBron, take note.
Recent history means that, for those who do actually work in finance, some connotations are almost unshakeable. No matter how Milanese your shoulder, people will still assume you’re an arsehole.
Finally, if you’re the kind of man who emailed tailor David August after Conor McGregor wore one of his suits, on which the pinstripes were in fact the words ‘Fuck You’ stitched in gold thread, then you clearly can’t be trusted to wear them properly. Best sit this one out.
5 Modern Ways To Wear A Pinstripe Suit
Avoid contrast-collar shirts, and pinstriped suits are surprisingly versatile. Here’s how to make yours feel sharp, not fancy dress.
Merge And Acquire
The pinstriped navy suit has taken a battering over the last couple of decades. But it’s a classic, and unlike the financial industry, classics don’t let a few bad apples ruin something for everyone. You just need to think different. “If you wear a three-piece suit with a grey pinstripe, you’ll look like a banker,” says McCalla. Instead, lose the waistcoat and play with your fit.
The look you’re going for is nonchalance. Old pinstripes were a power statement; modern pinstripes are anti-authoritarian. Brighter shades of blue feel sunny (and inappropriate on trading floors), particularly if you lose the socks and swap silk ties for linen.
Better yet, lose the collar and noose entirely to divorce yourself from the office. “I personally like breaking classic rules and clashing stripes and prints together,” says Morgans. A geometric knit conveys fashion confidence, not cocaine-for-lunch arrogance.
Break Up The Banks
The easiest way to wear a pinstripe suit is not to wear one at all. “Originally, trousers were the only thing that a man would wear that were pinstriped,” says Alexander. “And they still work really well with a block-colour blazer.” The split suit is tougher to pull off in reverse; pinstripes are so associated with suits that people will think you’re just wearing the jacket and had to change out of the trousers.
The separates approach is inherently more relaxed, so lean into that aesthetic by breaking every rule on the Morgan Stanley dress code: white trainers, not black shoes; a shirt that looks best without a tie (try a button-down, polo or crew neck); and a sense of decency and respect for your fellow man.
Gordon Gekko’s more is more philosophy extended beyond his bank account. As well as pinstripes, he leaned into accessories, draping himself in power ties, hot pink pocket squares, collar bars and cufflinks you could see from the top of the World Trade Center. This season, you should ditch it all if you want to pull off pinstripes.
“A pinstripe suit over a plain T-shirt [or roll neck], with nothing else going on, looks really clean and refined,” says McCalla. It’s a stripped-back aesthetic that works best with an equally minimalist pattern; think tonal pinstripes on grey tailoring rather than anything too flashy.
All that being said, it is still possible to wear pinstripes without being a wallflower. Recently, brands like Haider Ackerman, E. Tautz and Topman Design have blown up the pinstripe, switching from fine lines to zebra stripes. “We’ve also seen textured and metallic yarns that give a contemporary update,” says Morgans.
These disruptive patterns come bundled with new shapes, from wide-legged trousers to safari jackets, which riff on tailoring’s traditions. “Brands that have a suiting heritage are able to innovate in ways that respect the culture and background,” says McCalla. “They’ve got the authority to mix it up.”
These wilder looks aren’t even appropriate for business-casual offices, which means you can have fun everywhere from head to toe; try accessorising with chunky trainers and a beanie or baseball cap.
Greed isn’t good, but the classic pinstripe suit look can still work, whether you’re a City boy or just want to mix up your officewear rotation. A sober pinstripe in a dark navy still looks smart and sophisticated when all the constituent parts are done right.
Also keep your accessories, well, recessive. Pick a pocket square or a tie bar, not both. If you’re going double-breasted, you don’t need any embellishments. Okay, maybe a business card with Silian Rail lettering, Patrick.
The Brands That Do Pinstripes Best
As well as its excellent range of affordable tailoring, in which you’ll find slim-fit and skinny pinstripe suits that no Canary Wharfer could ever pull off, there’s also Topman’s envelope-pushing Design arm.
The brand’s directional wing takes a wild approach to striped tailoring, with cut-up shirts that clash vertical lines together, belted suits you might wear in the world’s best-dressed prison and contrast waistcoats that twist the idea of a three-piece into new shapes.
The Wall St look is more than a little stuffy for the Spaniards, so it should be no surprise to find Mango’s take on pinstripes skew casual. Think unstructured blazers and chore jackets with big patch pockets, looser-legged trousers and shirts that are better unbuttoned than corporate chokers. The chalkstripe lines are softer, too. If your annual bonus is taking you to the sun, this is what to pack.
For those who prefer their tailoring more traditional, Ralph Lauren cuts a fine line in not-quite-banker suits. Yes, you can get double-breasted navy pinstripes and yes, they come with a strong, no-nonsense shoulder.
But you’ll also find less structured preppy cuts, alongside trim and slim, modern updates on the 1980s classic. Perfect if you work anywhere other than a bank, but still want to bring a bit of that high-roller lifestyle to the office.
This titan of American tailoring gives you everything you’d expect if you have a Jordan Belfort-sized budget for your tailoring. The pinstripes are narrow and subtle, slicing through 100 per cent wool, hand-sewn suits with canvas construction.
And if you’re heading to the Hamptons for the weekend, the firm will kit you out seersucker pinstripes that are every inch as immaculate, if a lot less formal.
Italy is a nation more adept at fine tailoring than high finance, so it’s perfect for a suit that nails the former without shades of the latter. Lardini’s pinstripes are everything commodities traders aren’t: soft, refined, relaxed, and a pleasure to spend time with.
Its pinstriped blazers in particular are so unstructured they could double as a cardigan, particularly since the patterns are picked out in sumptuous shades of ocean blue. It’s the kind of suit a banker might wear once he’d sold up and retired to Tuscany.
The disruptive Dutch tailoring brand has a handful of navy pinstripes, but it also does a version of its youthful suits in white, light grey and brown. All of which tip things more modern. Equally interesting is its range of fabrics: alpaca, cashmere and linen offer unexpected texture and a level of depth you won’t find in finance.