When the Toronto International Film Festival rolls into town, it brings with it quality cinema, A-list celebrities and 10 nights of red carpet premiere parties. Considering this particular triad that is TIFF, it’s easy to understand how the festival coaxes out everyone’s inner-trendsetter.

With any number of reasons for festival goers to dawn a suit jacket between September 4th-14th, Hugo BOSS has teamed up with TIFF to design a pocket square that will help add a dash of panache to every gentleman’s party ensemble, on top of kickstarting a child’s love of film.

A spot of style to go with a charitable donation, proceeds from sales of the pocket square — a steal at $45.00 — will go to help support the TIFF Pocket Fund, an outreach initiative created to subsidize tickets and travel for underprivileged children and youth interested in experiencing the TIFF Kids International Film Festival and the organization’s educational workshops.

Philanthropic cinephiles don’t delay, this fashionable accessory is only available for a limited time at select BOSS stores across Canada.

In the spirit of the TIFF Pocket Fund, we take a look back at some of cinema’s most fashionable leading men, and the small, but integral, part the pocket square played in earning them their style kudos.

In The Great Gatsby, Leonardo DiCaprio stepped into his role of Jay Gatsby by way of a manicured world of look-at-me-glamour: money, parties, women and of course pink suits. Gatsby’s winged puff pocket squares were the finish touch to all his suits — pink or not — always matching either his vest or tie. How riche.

Stepping in and out of an Aston Martin, woman in one hand and a gun in the other, is all part of a 00 agent’s job description, according to the Bond franchise that is.  And while Sean Connery did make our heart skip a beat with his portrayal of the dashing secret agent, there’s something about the way Daniel Craig owns a suit that has every woman wish they were the one at home folding 007’s pocket squares.  Just as Bond completes his missions, his pocket square style is clean and tidy — a classic white scarf peaking out of the breast pocket. Cue swooning.

It’s never easy to be a hopeless romantic, especially when your heart is set on the matriarch of a dysfunctional family, kept together by a lie that is the difference between you losing the girl and you winning the girl. Enter Henry Sherman (Danny Glover) the noble truth bearer and Etheline Tenenbaum’s unlikely knight in…a tweed suit. The most stylish of Wes Anderson’s Royal Tenenbaums bunch, Sherman is a gentleman through and through, hence the perfection of his pocket squares. It’s a rare breed who can pull off a look that combines a bow tie, double breasted suit and an ornately patterned two-point pocket square without looking stuffy, and kindly Henry Sherman is just that breed. It’s just something about his face…perhaps it’s the little tabs of toilet paper on it.