One of the most iconic looks from Hollywood in recent times has come from the film adaptation of The Great Gatsby. Few men can pull off a pink linen suit with a white button down shirt. Now, part of the reason this worked was, of course, Leonardo DiCaprio. But the other name associated with this iconic image was Brooks Brothers. As much as Brooks Brothers has a stake in history –  at 199 years, it is the oldest menswear brand in the United States – the classic white button-down also has a historical significance. For one, not only was it a staple in Gatsby's wardrobe, it was also made popular by F Scott Fitzgerald, the author who created the character. In fact, his status as a fashion icon of the Jazz Age (1920s) might have propelled the button-down shirt's popularity amongst the bourgeoisie of the time. The button-down shirt first came to be in 1896. In modern design, the principle of "form follows function" defines the merit of good design; whether it is in terms of architecture or industrial/utility design of the 20th century. It wouldn't be wrong to say this applies to fashion too, and John E Brooks, grandson of the label's founder, was one of the first to demonstrate this. Shirt collars at the time were worn unfastened. While this seemed fine for quotidian purposes, Brooks realised how it could be an impediment, while he was at a polo match. He noticed that the polo players had sewn buttons to keep the collars fastened to prevent them from flapping around while they rode on their horses. Brooks took this concept back to his atelier and started offering button-down shirts under the Brooks Brothers label. These were marketed as the Original Polo Shirt and bear the tagline even today.   8   While Fitzgerald brought the button-down shirt to limelight, the surge in its popularity owes much to the Italian industrialist and style icon, Gianni Agnelli.  The chairman of Fiat and a notorious playboy, Agnelli was known for wearing his Brooks Brothers button-downs unbuttoned on top, and his watch on top of the cuff, creating a look called sprezzatura – a consciously dishevelled-yet-stylish look.  Contemporary iterations of the button-down shirt are seen everywhere, from corporate offices to George Clooney on his off-duty days. Here are three ways to wear this classic.

Off-duty Style

A button-down collar when fastened up can end up looking too formal, so pick a fun printed shirt and pair it with a pair of khakis or beige chinos for a more relaxed, off-duty look you could wear to a brunch.

Work Mode

A classic pinstriped button-down shirt, when paired with a jacket and complimentary tie, will help you make a power play in the boardroom.

Daytime Celebration

Eveningwear is pretty straightforward but daytime events can be confusing as far as a dress code is concerned. A pastel button-down, when paired with a navy jacket and a foulard instead of a tie can be your saviour on such occasions. Like this article? Also readBrand Now: Brooks Brothers