How To Wear Pinstripes

Getting on the straight and narrow has never been easier

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Think pinstripe or chalk stripe; think fat cats with a penchant for red braces and boozy lunches on expenses. Right? The fact is the finance sector pretty much invented pinstripe tailoring. Back in the early 1800s, when top hats and tails were de rigueur in London's Square Mile, the stripe on your trousers denoted which bank you worked for. The motif remained at the formal end of the spectrum in the UK, but our US pals quickly translated the stripes onto more casual navy two-pieces, "country" brown three-pieces and West Egg pastel get-ups in a way only Lindy-Hopping Long Islanders could.

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Shortly after, mobsters such as Al Capone adopted the look, and from then on, the pinstripe was associated with grisly Chicago massacres and tommy-gun turmoil. Decades later though, in the master-of-the-universe days of the Eighties, it found its way back into the heady world of finance, as mirrored in film by Gordon Gekko, Patrick Bateman and Leonardo DiCaprio's Jordan Belfort. In 2017, pinstripe (and vertical stripes in general) are well and truly back and being used in more interesting ways then ever seen before (none of which make you look like a financier and/or serial killer).

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"Pinstripes immediately convey a tailoring and menswear message," says Jason Basmajian, creative director of Cerruti 1881. "They are powerful, clean and classic. This season, I liked mixing up the scales and dimensions, as well as using new fabrications: linen, cotton blends, wool-silk, which give a more relaxed mood to traditional pinstripes. They feel right at the moment, when fashion is exploring and reinventing the codes."

On-point outerwear

Black/white striped wool-silk coat, £695, by Mackintosh. Ecru cable-knit wool roll-neck, £195; ecru cable-knit wool scarf, £95, both by Daks. Dark grey wool cropped trousers, £250, by Kent & Curwen. Black leather boots, £660, by Canali

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Double stripe

Mustard wool-cashmere greatcoat, £800, by Ami. Blue/white striped cotton shirt, £155, by Sandro. Grey/white striped wool trousers, £225, by Enlist. White leather trainers, £200, by Tiger of Sweden

Low-key weekend

Tan shearling double-breasted jacket, £1,480; white leather trainers, £240, both by Sandro. White cotton T-shirt, £75; black pinstripe wool cropped trousers, £265, both by Ami. White cotton socks, £12, by London Sock Company

Contemporary classic

Black/white chalk-stripe wool suit, £3,070, by Pal Zileri. Black lightweight wool roll-neck, £160, by Daks. Black leather shoes, £410, by Crockett & Jones