1. Alan Jackson Alan Jackson kept things cool at the 2009 ACM Awards in a crisp button-down, ornate blazer and denim jeans. © Kabik/Retna Ltd./Corbis
2. Carrie Underwood Carrie Underwood never fails to amaze us on the red carpet, but her 2014 ACMs dress really blew us away. With hints of silver and gold fringe, the “Good Girl” singer sparkled all night. © Nate Beckett/Splash News/Corbis
3. Charlie Daniels Outlaw country legend Charlie Daniels kept things classic at the 2004 ACMs with a cowboy hat and flashy belt buckle. He looked so good, even the Devil wouldn’t mess with him! © Steve Marcus/Reuters/Corbis
4. Dolly Parton No fashion list would be complete without including the beautiful Dolly Parton. The “Jolene” singer dazzled in a pink leopard-print dress as she hosted the 2000 ACM Awards. © Reuters/Corbis
5. Eddie Montgomery Montgomery Gentry’s Eddie Montgomery arrived at the 2011 ACMs wearing quite the bold, patriotic statement. His American flag jacket read, “Try To Burn This One,” and we certainly wouldn’t recommend anyone actually try! © Sam Morris/Reuters/Corbis
6. George Strait After four decades, George Strait continues to surprise us every year with his award-worthy looks. Keeping it simple with a white button-down and plaid blazer, George exuded an air of effortlessness at the 2014 ACMs. © STARPICZ/Splash News/Corbis
7. Ira Dean Singer Ira Dean never goes unnoticed on the red carpet, and his 2011 ensemble was one of the most memorable yet. Dean might’ve paired a couple unexpected items together—i.e. a fitted black cap, ’70s-style suit and sneakers—but somehow he made it work. © Jason Moore/ZUMA Press/Corbis
8. Jake Owen Jake Owen sizzled at the 2014 ACMs in his red suit. When you look this good, why settle for the norm? © Russ Einhorn/Splash News/Corbis
9. Jennifer Nettles Sugarland’s Jennifer Nettles looked sweeter than strawberry lemonade in her summer-ready gown at the 2012 ACM Awards. © Byron Purvis/AdMedia/Corbis
10. Jessie James Decker Singer Jessie James Decker looked absolutely radiant on the 50th ACM Awards red carpet, sporting the cutest accessory of them all—a baby bump! © MJT/AdMedia/Corbis
11. Kacey Musgraves Kacey Musgraves looked darling at the 50th ACM Awards in a pale-pink beaded dress. Her simple hair and natural makeup really made the outfit pop. © Paul A. Hebert/Press Line Photos/Corbis
12. Kimberly Schlapman The Little Big Town singer switched things up on the 2013 ACM Awards red carpet in a beautiful jumpsuit. Schlapman’s clutch and bracelet were gorgeous, too, but her No. 1 accessory will always be her bouncy curls. © Steve Marcus/Reuters/Corbis
13. LeAnn Rimes LeAnn Rimes’s career is filled with a long list of stunning red carpet looks, and her 2008 ACM Awards outfit—a Grecian-style flowing purple gown—was no exception. © Andrew Gombert/epa/Corbis
14. Lee Brice Lee Brice kept things cool at the 2014 ACM Awards by sporting a backwards baseball cap and slick, black suit. © STARPICZ/Splash News/Corbis
15. Loretta Lynn Loretta Lynn took us back to the prairie in her beautiful white peasant dress at the 2004 ACMs. The frilly bell sleeves were just the icing on the cake. © Ethan Miller/Reuters/Corbis
16. Martina McBride Martina McBride arrived at the 2007 ACM Awards looking regal in a plunging purple gown. A crystal-encrusted chain draped around her waist, which also added a magical touch. © Chris Farina/Corbis
17. Miranda Lambert If there’s one thing Miranda Lambert’s better at than winning awards, it’s lighting up the red carpet. Her 2014 ACM Awards look will go down in history for it’s simple elegance. © Keene/Splash News/Corbis
18. Reba McEntire Reba McEntire consistently proves she’s not only a legendary singer, but she’s also a fashion goddess. The lavender gown she wore to the 2010 ACMs will always be one of our favorites. © RD/Erikk Kabik/Retna Ltd./Corbis
19. Rissi Palmer Rissi Palmer looked ravishing in red at the 2008 ACM Awards. Even though her dress was the same color as the carpet, Palmer’s beaming smile made the singer pop. © Kabik/Retna Ltd./Corbis
20. Shania Twain Shania Twain kept things flirty and fun in a high-low black dress with just a touch of leopard print at the 2003 ACM Awards. Add strappy heels and a chunky cross necklace, and her outfit was just as memorable as any one of her many hits. © Frank Trapper/Corbis
21. Susie Brown Susie Brown of The JaneDear Girls was stunning in a ’40s-inspired silky red dress at the 2011 ACMs. Who says young stars can’t pull off Old Hollywood glamour? © Amy Harris/Corbis
22. Taylor Swift Taylor Swift is as much of a fashion icon as she is a multi-genre superstar, as illustrated by the classy two-piece she wore to the 2014 ACM Awards.© Splash News/Corbis
23. Tobi Lee Wild-child Tobi Lee of Mustang Sally made a huge statement when she arrived at the 2013 ACMs in a funky leopard print dress complete with a voluminous tutu skirt. © Steve Marcus/Reuters/Corbis
24. Toby Keith Country bad boy Toby Keith’s 2004 ACM Awards look is hard to forget. Dressed in a denim shirt and red bandana, Toby definitely doesn’t need a black suit to make a fashion statement. © Laura Farr/ZUMA/Corbis
25. Ty Heardon Dressed in red leather, it’s a wonder that singer Ty Herndon didn’t overheat at the 2001 ACM Awards. Guess when you’re already a hot country artist, you don’t even notice the weather! © Frank Trapper/Corbis
26. Willie Nelson With his signature braids and black cowboy hat, Willie Nelson even made a cast look cool at the 2004 ACM Awards. © Lisa O’Connor/ZUMA/Corbis
27. Wynonna Judd Never one to shy away from taking risks, Wynonna Judd she can pull just about anything off, both music and style-wise. This ornate suit paired with purple boots at the 2003 ACM Awards will never be forgotten. © Frank Trapper/Corbis
28. Faith Hill The only thing more beautiful than a Faith Hill ballad is her look on the 2014 ACM Awards red carpet. She looked ethereal in a blue gown. © Steve Marcus/Reuters/Corbis
29. Aaron Tippin Country artist Aaron Tippin was a walking sandwich board for what he expected from the 2006 ACM Awards. Can’t blame a man for wanting to party at the country music’s biggest event of the year! © Mike Valdez/ZUMA/Corbis
30. Billy Gibbons With a beard as long as his, it’s hard to ever forget a “Sharp Dressed Man” like ZZ Top’s Billy Gibbons. But he doesn’t just let his facial hair do all the talking: Billy hit the 2006 ACM Awards red carpet in a funky blazer and one of his signature wacky hats. © Mike Valdez/ZUMA/Corbis