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Aleks Cvetkovic charts the checkered history of the chalk stripe. 

The chalk stripe, rather unfairly, has a reputation for corporate conformity. True, it’s synonymous with city suiting and the legal profession, but its roots precede the uniforms of middle-class professionals, stretching back into the late 18th and early 19th centuries.

In fact, stripes in their earliest form were seen as quite informal. Dress trousers, similar to today’s ‘spongebag’ grey striped morning trousers, were worn with black frockcoats or tailcoats for what was known as ‘day dress,’ or ‘half dress’ – that is to say, for the less formal situations in a gentleman’s day-to-day. It was only really the rise of the 20th century businessman that put paid to the stripe’s apparent casualness, with the plain worsted cloths of formal ‘full dress’ relegated to lounge suit territory, in the stripe’s place.

Named after its soft, mottled appearance, the chalk stripe was subsequently adopted by modern city slickers in the 1910s, firstly as the uniform of corporate big wigs (in many British and American finance firms, only the top ranks of bankers were permitted to wear inch-apart stripes – an unofficial marker of their status), and latterly by mafiosos looking to give a powerful, but above-board impression to society at large. ‘Oh, Mr. Rothstein, what do you do?’, ‘Why I’m a philanthropist, madam’.


Today, chalk stripes are still primarily worn for business, but that doesn’t mean they need to be bland. One of the great powers of Drake’s is to take stiff, formal clothes and somehow relax them –making them both understated and cool in the process.

Here, they’ve done this by cutting a sober navy woollen flannel in the Drake’s house style. Robust winter cloths (particularly dense flannels like this) suit an unstructured silhouette: there’s no internal structure or shoulder pads to fight against the heft of the cloth, so it settles into the wearer’s figure, moulding comfortably to his body. The Drake’s three-roll-two button stance, patch pockets, and single-pleat trousers with side buckles reinforce this easy-wearing impression.

A suit like this feels most at home other deep colours and simple shirts. The team from Drake’s has dressed it with a plain white poplin point collar shirt and a rich forest green 36oz madder tie (whoever said ‘blue and green should ne’er be seen without a colour in-between’ was talking piffle), which will work equally well in the office as during a smart dinner out. The preppy addition of a navy and burgundy hoop striped rugby shrugged over the shoulders introduces a third colour into the mix, which is rich enough to sit against navy flannel and green silk.

Not that you always have to pair a navy chalk stripe with like colours – it’s a restrained base for a tailored look, after all. Mixing it with light checked shirts or this season’s bright stripes works just as well. I also like navy flannel with a washed blue denim or chambray shirt and a vibrant printed tie, or a heavy repp tie with regimental stripes. It even works with a warming lambswool rollneck – wear with the Drake’s cream or forest green options on a chilly morning.

However you choose to wear it, a navy chalk stripe suit’s strength is in its classicism. It’s nice, occasionally, to revel in the sense of security that a stripe brings to the table. You’ll feel prim and proper when you need to look the business, but it’s also a suit with which to bend the rules, too.

And, as we all know, bending the rules is half the fun.

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