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Patterns for the Adventurous Man: Timeless Pinstripe

Truth be told, the solid navy blue suit will never go out of style. There is something so extraordinarily refined about a well-tailored monochromatic suit that requires a man always keep one on hand for a variety of different occasions.

Indeed, the solid, dark-coloured suit is one of the most versatile and tastefully minimalist garments for men the world over. There are times when the need for a bit of edge or shot of personality outweighs the comfort of a classic suit jacket. At these times, a man of adventurous and particular style will venture into the world of patterns. Shapes, angles, and lines form a distinct canvas for the suit, which evokes a particular image for the wearer.

As with anything else deemed unordinary, however, patterns can be as disastrous as they can be outstanding. We pride ourselves on knowing the intricacies of men’s style, and our knowledge of patterns is no different. This is just the beginning of patterns for the more adventurous man, so if you’re looking to branch out from your everyday solid navy suit, please do read on.


In the 21st century, the pinstripe suit is a mainstay of professional style for men and even women. It was not always this way. Although there isn’t a clear consensus on the origins of the pinstripe suit, there are a few respectable theories that historians and style buffs purport. Some believe that the pattern was inspired by striped military uniforms, while others claim that it was derived from a late 19th-century boating suit that utilised thin dark stripes on a cream coloured background. Whatever the case, the pinstripe suit has been with us since at least the 1920s and is still worn by men all over the world today.

Pictured here from the movie The Philadelphia Story is Cary Grant and James Stewart in Double Breasted Pinstripe Suits along side John Howard with Katherine Hepburn in the centre. Photo Credit: The Fashionisto

It’s interesting, however, to note that the pinstripe suit was considered flashy and overwhelming when it first began to catch on in the 1920s. This likely explains why the suit was initially well-received by more rebellious types, such as American gangster Al Capone. Even to today, bolder pinstripe suits with more of a contrast between dark and light are associated with the style of organised crime in the early 20th century U.S. On another note, the Chicago Cubs were the first sports team to wear pinstripe uniforms and have been doing so since 1907. This also would have made wearing a suit of the same pattern seem a bit outlandish for conservative business men and professionals.

The suit caught on and today is worn without a second thought by men in all sorts of professions, ranging from finance to law, to politics. In many instances, the pinstripe suit comes off as more formal, even regal, than a traditional solid dark-coloured suit. Unlike many other patterns, a full pinstripe suit, with both jacket and pants matching, carries a sophisticated and professional air, rather than a flashy or tacky one.

Still, even with something as timeless and elegant as the pinstripe suit, there is room for error. Colours and the right amount of contrast are key to the perfect pinstripe suit, so try to avoid a stark black and white pattern. Instead, aim for the more subtle contrast of a light grey on a soft charcoal or even a powder blue on a dark navy. Pinstripe is easy to spot and recognise, so there is no reason to over-emphasise. Also, the detail of added shades of colour will give you the opportunity to experiment with a variety of shirt colours. Don’t be afraid to stray from the classic white shirt when sporting pinstripes—depending on your skin tone, a pale pink or blue can help by adding liveliness and energy to a rather serious suit.


Pinstripe Pairing Inspiration

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