How to Dress Like Brad Pitt and Leonardo DiCaprio in “Once Upon a Time in Hollywood”

There’s a lot packed into Quentin Tarantino’s ninth film.

Once Upon a Time in Hollywood features, in no particular order: Spaghetti Westerns, acid-dipped cigarettes, Bruce Lee, the best dog acting since Air Bud, Los Angeles freeways not jammed with cars, Kraft Macaroni & Cheese, hitchhiking hippies, flamethrowers and a whole lotta feet.

We’ll let the rest of the internet play armchair critic and decide where this ranks in Tarantino’s canon; we’re here to talk about the film’s vibe, specifically how 1969 Southern California is worn on the shoulders of actor Rick Dalton (Leonardo DiCaprio) and his stuntman Cliff Booth (Brad Pitt).

Each of the protagonists has his own distinct style, and because the majority of the film takes place over a single weekend, their outfits are almost characters unto themselves, which meander from bizarre to familiar to iconic as the lengthy film stretches on.

Below, find the closest imitations we could find of all the Hawaiians, leather jackets, sunglasses and boots worn by Dalton and Booth in Once Upon a Time in Hollywood. It probably would’ve been easier to drop links for Gucci and Prada throughout, but as you don’t have the unholy budget of a Hollywood costume designer, we made sure to source options on the more democratic side.

Rick Dalton

Rick’s a has-been TV star in crisis, but he still, at least, has an address in Beverly Hills. That means he’s always dressed to immediately take a famous neighbor up on a pool party invite. Dalton sports tailored leather jackets, has a collection of musty red, yellow and beige turtlenecks, and often wears a gold chain with a circular pendant across his chest. Taken out of context, or attempted faithfully in 2019, this look is probably on the goofier side. But when these pieces are mixed and matched — pair the jacket with the boots and your favorite pair of jeans, or tuck the turtleneck into those pants and get yourself a blazer — outfit options abound.

Motorcycle Jacket
Thursday Boot Company

Easy Fit Roll Neck in Camel
John Smedley Sweaters

Torino Classic Fit Flat Front Solid Trousers
John W. Nordstrom

Corey Lace-Up Boot
Frye

George Frost Shield Necklace
Lulu Frost

Cliff Booth

Cliff spends most of his days driving around LA or getting into fights, and makes sure to dress comfortably for the potential of either. He lives in a trailer in the lot behind a drive-in movie theater, so it’s unlikely he’s bought new clothes in a long time. This charismatic outfit then, the yellow Hawaiian, the faded Champion tee (which matches well with the Wheaties in his kitchen), the Levi’s jeans and exhausted boots, feels like a beloved, reliable curation of his limited wardrobe. It’s also far more replicable than Dalton’s look. You can and should wear this full ensemble to the bar on the weekend.

Palm Dreams Woven Shirt
Banks Journal

Reverse Print Logo T-Shirt
Champion Auto Parts

1967 505 Regular Fit Men’s Jeans
Levi’s

Two Button Hardsole Boot
Minnetonka Moccasin

60mm Polarized Aviator Sunglasses
Cole Haan

Holmes Reversible Leather Belt
Robert Graham