A Complete Timeline of How Cowboy Style Got so Cool Again

Double denim, henleys, and shearling entered heavy rotation last year, and look on track to make an even bigger impact on style culture in the year ahead. Menswear has officially circled the wagons around Western-inspired duds. Here’s how we got here.

February 2017

Raf Simons debuted a cowboy boot–laden collection for Calvin Klein — a warning shot, pardner.


June 2018

Season 2 of country sci-fi thriller Westworld ended, but not before our obsession with cowboy hats took hold.


January 2019

Bradley Cooper’s country-star drawl (and his khaki denim jacket) nabbed an Academy Award nom for Best Actor in A Star Is Born.


April 2019


Atlanta rapper Lil Nas X’s remix of “Old Town Road” with Billy Ray Cyrus had social media swigging “yeehaw juice” in corduroy. The song achieves Diamond certification from the RIAA in October.


January 2020

Photo by Christian Vierig/Getty Images

Cowboy hats, boots, and jackets are all unexpected street style fixtures in Florence during the 97th edition of menswear Pitti Uomo.

January 26, 2020

Photo by Frazer Harrison/Getty Images

An incredible 24 hours in cowboy culture. First, Halsey rides a mechanical bull during her Saturday Night Live performance in the early hours of the morning, and then the Grammy Awards the following night welcome no shortage of western style, with Orville Peck, Diplo, Lil Nas X, and Billy Ray Cyrus all gracing the red carpet in cowboy hats. Country is back, y’all!

February 2020

You buy and immediately question the purchase of a pair of bold leather cowboy boots that your friends will probably tease you about. But we support them! And hey, the Calgary Stampede is only five months away.

$1,400 at Mr Porter