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Country music doesn't get much shine here on Complex, but go back a few years and the leading men of this genre were some of the freshest looking guys making big moves. Originating in the dirty South, country was very much about the people and for the people. Its subject matter ranged from the simple pleasures of life to social rebellion to fast living, and the leading men were dressed as diversely and as awesomely as the music.
Whether these OG rockstars were wearing simple but functional garb that was typical of its blue collar audience, or colorful suits that matched their celebration of life, or somber dark clothing that expressed their outlaw nature, country music gave rise to some of the most colorful personalities and senses of style we've ever seen in music. Currently, it seems like all country stars are trying to look like cheesy Hollywood stars, which is a shame but wasn't always the case. We looked past the Taylor Swifts and the Tim McGraws to find The 10 Most Stylish Country Singers of All Time.
10. Willie Nelson
While he may have gotten recent attention for being the only person able to outsmoke Snoop Lion, Willie Nelson is also a dude with some serious rebel style that fits perfectly with his anti-establishment attitude and music. W
illie was one of the founders of outlaw country, a sub-genre of country music that was mostly a big "fuck you" to the corniness that the music industry Nashville had become by the late 1960s. With his signature headband, long red hair, and proud drug usage, his whole manner of being and style was one big flipping off of the industry and The Man.
9. Hank Williams Jr.
Most of Hank Williams Jr.'s early days were spent in the shadow of his legendary father, Hank Williams (more on him later). Style-wise, this wasn't necessarily a bad thing. Junior looked great in the '60s, but wanted to forge his own path. After finding drugs, alcohol, and a Southern rock influence, his music became known in its own right, and he definitely stopped dressing like his Pops.
After a brutal mountain climbing accident in 1975, Hank grew a beard and wore sunglasses and a cowboy hat to cover up his scars and disfigurements. The look soon became his signature style, and co-incided with his rise to superstardom. Now you know him as that guy you heard every Monday night until he made some seriously controversial comments.
8. Gregg Allman
Born in Nashville, the epicenter of country music, Gregg Allman incorporated all types of rock 'n roll into The Allman Brothers Band's music. Country, blues, psychedelic, and Southern rock all conflated to create an original sound that was hugely popular as soon as the nation got a chance to hear it. Gregg was definitely the trippiest looking country singer out there, but he was a certified rockstar and thus could do whatever the fuck he wanted. This included marrying Cher and dressing so kooky that the extra "g" in his name most definitely stood for gangster.
7. Jimmie Rodgers
Jimmie Rodgers, who became known as "The Father of Country Music," was taught to play as a child by railroad workers and train-hopping hobos. Different times, the 1910s were. He set the stage for future country singers by dressing like the common people he set out to entertain, as well as donning classic American suiting, which was also a staple of the working man way back then. Almost every country singer who came after "The Singing Brakesman" owed much to this man, both for their sound and setting the starting point of country music's style evolution.
6. Gene Autry
Gene Autry is considered the second biggest influence on country music after Jimmie Rodgers. Known as the "Singing Cowboy," Autry starred in an absurd number of movies from the 1930s to the 1960s, and is widely credited with bringing country music to the attention of a national audience.
As the genre's biggest stars on the big screen and on TV, it's a damn good thing Autry dressed the way he did. In cowboy gear that was both practical and looked good, he was the archetype of the straight-shooting hero who personified bravery, honor, and style.
5. Ray Price
Ray Price was one of the original supporters of Nudie Cohn, and he definitely rocked some of the famous tailor's most awesome creations. He is considered one of the pioneers of 1950s honky-tonk music, and when a genre you help make popular is synonymous with bars that cater to guys who are looking to get wasted, you better dress like a party animal. Ray Price did not disappoint, and he continues to wear flamboyant clothing as he continues to ball out in his late 80s.
4. Jimmy Martin
Jimmy Martin was known for two things: being the "King of Bluegrass" and having a personality that unpredictably swung between being a violent asshole and being the exuberant life of the party. Martin's fun-loving and hard-partying persona was definitely reflected in his wild style of dress. From the impoverished countryside of Tennessee, Martin showed off his success and personality in bright garish customized suiting that upped the fashion ante on all his contemporaries.
3. Waylon Jennings
Alongside Willie Nelson, Waylon Jennings was the OG outlaw singer. No one else embodied the fast living of country music's rebel lifestyle more so than Jennings. His signature long hair and beard (unheard of in Nashville in the early '70s) and black leather vest were symbols of his rebellion and spoke to a new audience of country: the youth who were disaffected by the failed utopia of the '60s.
2. Hank Williams
Widely considered the greatest country music singer of all time, Hank Williams only lived to the age of 29 but left a lasting legacy of music and style. When the most prominent country singer starts donning Nudie Cohn suits, anyone who was paying attention in Nashville was going to start jocking his steez, giving rise to one of the more colorful trends in recent history. Hank put country music and its unique style on the map for good.
1. Johnny Cash
If you thought Kanye West, Jay-Z, and A$AP Rocky were the first ones to dress all murdered out, then allow us to introduce you to the guy who was simply known as The Man in Black. Johnny Cash rocked all-black everything in mourning for the perpetually downtrodden people he came across in his travels, and looked damn good doing it.
This champion of the people transcended country music to become known as one of the most influential musicians of his time. His romantic outlaw image essentially founded the notion that any desperado cool guy could express his bandit and anti-establishment mentality in all black garb.
