First up, our favorite dress code dealbreaker: the shirt. DiCaprio has depended on simple (but rest assured, stylish) takes on this design since the dawn of his career. Pictured here in the late 90s, the actor opted to pare down his formal suit with a dusty brown shirt, collar unbuttoned and pulled over the lapels of his jacket for an effortless effect. Consider it your ultimate starting point for any type of event. This offering from French brand A.P.C. is the safest bet for the season ahead, tailored from cotton-corduroy and finished with two parallel front pockets.

DiCaprio’s style archive may not be defined by bold statements, but his strong set of menswear staples is second to none. In this 1993 moment, he wore a white t-shirt, layered under a black crew neck sweater that was loosely draped over straight cut indigo jeans. Finished with minimalist accessories (shoutout to the wallet chain), the result was an easy style win that can lend itself to any age and season. To recreate the look, check out Mr Porter’s Slim-Fit Merino Wool Sweater, and partner it with worn-in denim by Husbands Paris. Less is more, as they say.

If your style revolves around tailoring, a change in sartorial texture is key to battling the biting temperatures ahead. The best one, according to DiCaprio: velvet, as demonstrated by this excellent head-to-toe black ensemble he sported during Milan Fashion Week. Worn with a knit polo shirt and black twill trousers (both failsafe staples), the rich fabric of his finishing layer brought some texture to his simple style move. The outfit is brilliant inspiration for the fast approaching party season, and no house provides velvet flair better than Gucci.No spoilers, all the style

As the frontman of Once Upon A Time… in Hollywood, DiCaprio was blessed with a strong set of on-screen style moments, largely centered around 70s shades, leather jackets and ultra-hip sunglasses. And it’s safe to say this had some influence on DiCaprio’s personal style. During the film’s press tour, he stepped out in a slick suede bomber jacket, crew neck t-shirt, black washed denim and lace up sneakers. The bomber is designed to flatter every body type, so we suggest investing in this supple style by Officine Générale to see you through the decades. Pair it with Veja sneakers for chic all-day comfort.

If there’s one thing every man should have waiting in his wardrobe, it’s a tuxedo. And, unsurprisingly, DiCaprio is a winning case of how to approach it with ease. Pictured here at Hollywood’s most noteworthy event — the annual Academy Awards — the actor opted for a single-breasted style, designed with satin peak lapels and a soft shoulder line to bring out the broadest part of his silhouette. With the festive season looming, now is the time to invest in a well-crafted jacket and trousers, and no tailor does it better than Edward Sexton. Finish the look with your best bow tie and patent oxford shoes for maximum DiCaprio effect.This article was featured in the InsideHook newsletter. Sign up now.