Iconic Style: How to Dress Like Bad-Ass Clint Eastwood

In choosing what to wear, the rugged archetype of masculinity has always been an inspiration of men. The rough nature of a denim jacket or a pair of beat-up leather boots is almost nostalgic for a man, as if these objects are prying into the nature of who we are.

Clint Eastwood emulated this style of dress very well. The pieces he wore echoed who he was—an icon of masculinity, specifically the rough-and-tumble kind. Here, we list down a few things he was known, the essentials you need right now.

1| Clint Eastwood wore rugged fabrics.

IMAGE Paul del Rosario

We don’t expect everyone to go full cowboy, but it’s always nice to incorporate an element of ruggedness in what you wear, and the easiest way to do this is via the fabrics of your garments. Denim is always a fine choice, and besides the ubiquitous pair of jeans, a jacket or shirt in the fabric almost always looks good on anyone.

For days when you’re allowed to be more casual, switch your broadcloth dress shirt for something with more texture like twill, chambray, flannel, or even oxford in a coarser weave. And when the weather gets chilly, you can’t do any better than a hefty leather jacket. Avoid those made of leatherette or jackets that look too clean and invest in one made of real cowhide leather. These will age handsomely the more you break them in.

2| Clint Eastwood wasn't afraid of work boots.

IMAGE Paul del Rosario

Most men may find work boots too costume-y, but you don’t need to be Rowdy Yates from Rawhide or the Man With No Name from all those spaghetti Westerns Eastwood starred in to pull these off. The roots of work boots go back to the heavy physical work done by the proletariats of yore, but now it’s best to treat it just like any other casual shoe.

Wear it with a T-shirt or a henley and a pair of blue jeans to echo their rugged appeal, but if you feel like dressing up, a chambray button-down and chinos work just as well. But don’t go overboard and pair them with suits. These are casual footwear, and that’s really where it ends.

3| Clint Eastwood probably knew about wabi-sabi.

IMAGE Paul del Rosario

That’s the Japanese term used to represent an aesthetic centered on imperfection and impermanence. Remember this concept when you wear your clothes. The more you wear a piece of clothing, the more it changes it form: Colors fade, fits grow and shrink, leather ages and wrinkles, and that’s the beauty of it.

A well-worn garment is personal and has a sense of soul unlike something pristine you just bought off the rack. Embrace the beat-up character of your clothing. Besides, if something is of excellent quality, like fine wine or barrel-aged whiskey, it can only get better with time.

ILLUSTRATOR Alysse Asilo