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Style Advice

A brief history of pinstripes

A brief history of pinstripes

We’ll let well-dressed bankers and the New York Yankees fight it out over who wears pinstripes better. But when it comes to who wore it first? There’s a bit of a historical tug of war there too. Many argue it was bankers in Victorian-era London to first wear the spaghetti-thin stripe. It was, after all, common during that time to wear stripes on your suit that identified which bank you worked for. But others are sure it was 19th-century sailors who started the trend. It wasn’t uncommon during that time to borrow sartorial inspiration from sportswear. It still isn’t, as you well know. 

Today, the aesthetic established by both camps still lives on. There’s still the dapper approach to pinstripes, seen in scenic corner offices and flashy red carpet events. But there’s also a more casual approach to the stripe, and we’re not just referring to the iconic Yankee uniforms. There are casual knits, t-shirts, button downs, and accessories that all offer a more casual access point into the print. 

Both approaches to wearing pinstripes have earned their place in the wardrobes of every guy, but there’s also a middle ground that feels especially apt today, when blending high and low dressing is the new style frontier. Take the outfit styled by Freddie Kemp above. He plays with expectations by incorporating a pair of formal pinstripe trousers, but he dials things down by offsetting them with a pair of Converse trainers and a workwear-inspired jacket. With a simple swap of the shoes, it’s a look that will take you from smart casual work environments to after-work dinner. 

Because of the subtlety of pinstripes, Freddie shows it’s possible to wear another stripe in your look without clashing – for days when you want to take a style swing at head-to-toe stripes, but leave the real swinging to the Yanks.


Words: Allison Pavlick
Photography: Angus Williams
Styling: Freddie Kemp