In celebration of the 2020 Academy of Country Music Awards on Sept. 16, Wonderwall.com is taking a look back at the event's red carpet from the year 2000 to see how country's best singers and musicians dressed to impress. Let's start with Faith Hill and Tim McGraw, who'd been married for three years when they attended that year's show in Universal City, California. Keep reading for a closer look at Faith and Tim's fashion, plus more nostalgia-inducing style moments from one of country music's biggest red carpets 20 years ago…
Faith Hill took home her third consecutive female vocalist of the year award at the 2000 show. She arrived wearing a slinky silver dress with a high neckline and equally high slit over her thigh. She accessorized with a matching bangle and rocked heavy eyeshadow, making it a classic look of the era.
Tim McGraw's timeless style was on display at the 2000 Academy of Country Music Awards. The country singer wore his classic cowboy hat along with a dark suit and darker shirt underneath. Tim's style has remained so consistent and he's aged so well, this photo looks like it could have been taken at the 2019 show!
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In 2000, Reba McEntire — a frequent ACM Awards host — took a break from the gig to attend like any other country singer. On the red carpet, the redhead wore a slinky blue heavily beaded gown with delicate jewelry. The dress has withstood the test of time and could easily be worn at any major award show to this day.
In 2000, the then-Dixie Chicks, who in 2020 changed their name to The Chicks, took home the award for top vocal duo or group and album of the year for "Fly" at the 2000 ACM Awards. While walking the red carpet — with a bulldog — Natalie Maines choose a conservative and somewhat casual pink leather tea-length dress. Emily Erwin wore a one-shoulder white midi-length dress with an asymmetrical hemline and Martie Erwin rocked a colorful short frock with bold eyeshadow.
Dwight Yoakam delivered his own brand of country cool in a purple three-piece suit accessorized with white boots and a cowboy hat in the press room at the 2000 ACM Awards.
For the May 3, 2000, award show, Lee Ann Womack wore a yellow halter dress with a flower print with then-popular heavy eyeliner and styled her hair in an updo.
Wynonna Judd performed at the 35th Annual ACM Awards, which were held in Universal City, California. For her performance, she wore black sparkly pants, a black cardigan and a black shell underneath. To complete her look, she wore a matching black cowboy hat.
For Sara Evans' 2000 ACM Awards red carpet appearance, she wore a strapless, plain blue dress. Her very '00s look seemed like something one could have worn to the prom, or a look perfect for a bridesmaid in a wedding.
Naomi Judd went a little out there for her 2000 ACM Awards look. The singer choose a two-piece shimmery blue suit featuring flared pants and extremely wide sleeves that provided somewhat of a mermaid feel.
Clint Black and Lisa Hartman Black took home the award for vocal event of the year with their song "When I Said I Do" at the 2000 ACM Awards. Chris wore a black-on-black suit with a black cowboy hat, not unlike what Tim McGraw went with. For her big night, Lisa wore a shimmery two-piece set featuring a deep neckline and a long skirt worn low on her hips.
Fashion has not changed much for men and Kenny Chesney is no exception. The singer wore the seemingly required black cowboy hat along with a simple white long-sleeved shirt and black pants at the award show 20 years ago.
Martina McBride arrived at the 2000 ACM Awards wearing a sparkling midnight blue gown that resembled a night sky.
A shimmering, neutral-hued spaghetti-strap dress featuring floral embellishments paired with a delicate matching wrap was country queen Tanya Tucker's fashion choice at the 35th Annual Academy of Country Music Awards in 2000.
In 2000, SHeDaisy won the award for top new vocal duo or group. Sisters Kristyn Osborn, Kelsi Osborn and Kassidy Osborn dressed up for the special night with sparkle all around. Kristyn wore a silver two-piece suit, Kelsi chose a low-cut black top with a lacy skirt and black sequined jacket and Kassidy rounded out the shimmer and shine with a sequined black dress and long jacket.
Jo Dee Messina was on-trend at the 35th Annual Academy of Country Music Awards in 2000 in her midriff-baring long-sleeved blouse paired with sparkling embellished trousers.
Singer Amanda Wilkinson picked an interesting pairing for her walk down the ACM Awards red carpet in 2000: a bright pink bottom featuring a bright pink-and-silver flower print with a black sequined tube top.
Shelly Ray leaned into a few prevalent trends when she walked down the ACM Awards red carpet in 2000. The singer chose a two-piece set that featured a long, shimmery skirt in a light gold color and a creamy satin long-sleeved shirt that bared her taut belly.
Coley McCabe was not afraid of a bright color when she picked out her outfit for the ACM Awards. The singer choose a short-sleeved pink crop top and paired it with everyone's favorite at the time — a long, shimmery matching skirt!
Pam Tillis also leaned into the long skirt trend, but unlike her peers, she went for a darker look. The singer wore a blue satin skirt with a wild cat print and a black button-down on top. She accessorized with a cool pair of small sunglasses and a scarf to match her skirt.
Top new female artist winner Jessica Andrews chose a classic red carpet look for the 2000 ACM Awards. Jessica's two-piece look paired a conservative, sleeveless high-necked black top with a sparkly blue skirt.
Identical twin sisters Heather and Jennifer Kinley of The Kinleys attended the ACM Awards together. The siblings walked the red carpet in anything but identical outfits, with one twin favoring a classic black evening gown and updo and the other preferring pants and a cropped button-down along with a casual, beachy hairstyle.
Singer Danni Leigh combined the fashion of both the men's and women's country music stars with this ensemble. She paired low-rise pants with a cropped sparkly jacket but dressed the outfit down with a gray cowboy hat. Like many of her peers, she also favored the heavy eye makeup so popular at the time.