1999 ACM Awards fashion flashback

By Bryanne Salazar 8:06am PDT, Apr 3, 2019

Are you as excited as we are for the 54th Annual Academy of Country Music Awards? In honor of the 2019 ACM Awards, which air on April 7, Wonderwall.com is taking a peek back at 1999 to see who wore what on the red carpet… starting with Tim McGraw and Faith Hill. This dynamic duo looked anything but blue in their complementary navy styles. Tim showed his playful side in a metallic pinstriped suit and black cowboy hat while Faith tickled our spidey senses in a sleeveless web-embellished gown with delicate sequin detail and a thigh-high slit. This legendary country music couple were also competing against each other in the same category for best album. Although neither won that particular award, they took home the best vocal event of the year trophy for their duet "Just To Hear You Say That You Love Me." Keep reading for more…

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The Dixie Chicks were a kaleidoscope of color at the 1999 ACM Awards. Emily Robison (left) invoked an orange genie in a sequined crop top and tie-dyed skirt while Natalie Maines (center) paired a sky-blue mini with a matching metallic floor-length duster. Martie Maguire (right) went all pink in a baggy velour pantsuit with pink feather-boa trim and peep-toe pink platforms. While their fashion missed a beat, their music didn't. The trio took home the award for best new album and best new vocal group.

Friends Marie Osmond and Billy Ray Cyrus were captured in this funny photo at the 1999 ACM Awards. Marie, who was seven months pregnant at the time, wore a black shift dress with a matching beaded duster. Billy rocked a mullet, leather pants and an embroidered tuxedo jacket.

Here's country music icon Reba McEntire striking an alluring pose in a cream-colored gown with crocheted straps and a matching shawl. Reba was nominated that night for best vocal event for her duet "If You See Him/If You See Her" with Brooks & Dunn.

If you needed proof the '90s weren't the best decade for fashion, then let us present a young LeAnn Rimes, who arrived on the 1999 ACM Awards red carpet in this tragic all-black look. The combination of her lacy cardigan paired with a black tank top, slacks and a too-small-for-her-head cowgirl hat made us want to turn back time and help the teenage singing sensation find a more flattering style.

Looking like a linebacker, country star Toby Keith and his impossibly broad shoulders made an appearance on the 1999 ACM Awards red carpet. Nominated that night for best video for his song "Getcha Some," Toby went full cowboy in this navy blazer paired with a blue button-up, light-wash jeans, a white cowboy hat and a double-wrapped gold neck chain.

Best song and best single record nominee Martina McBride brought a pop of sunshine to the 1999 ACM Awards. While her shimmering gold and yellow damask-print gown definitely added some radiance to the award show, we can't help but notice that the color also seemed to wash Martina out.

We're calling Trace Adkins' 1999 ACM Awards look "Victorian cowboy." Standing beside wife Rhonda Forlaw, the country crooner rocked some serious turn-of-the-century vibes in this elongated frock coat, vest and black satin puff tie.

Best single record nominee Shania Twain had a dress coat that did double duty at the 1999 ACM Awards. At first glance, it appeared that the "Still the One" singer was wearing a sexy leopard-print wrap dress on the show red carpet. In a fun twist, it turns out Shania wasn't wearing a dress at all. Keep reading to see what this look transformed into…

It turns out Shania Twain's leopard-print dress was actually a cape-duster that covered her chic black bandeau top and matching velvet palazzo pants. We're calling her a fashion genius for maximizing her style while also prioritizing comfort.

At the 1999 ACM Awards, friends Eddie Montgomery and the late Troy Gentry of Montgomery Gentry were enjoying newfound fame following the debut of their first studio album just a month earlier. Wearing long trench coats, denim and lots of leather, the two managed to invoke both country and rock 'n' roll.

English actress Jane Seymour was a surprise attendee at the 1999 ACM Awards. The "Dr. Quinn, Medicine Woman" alum hit the red carpet in this heavily beaded and embroidered black-and-silver evening gown, which she paired with a silver clutch and matching sandals.

Country music star Terri Clark skipped the evening gown and went for stylish comfort at the 1999 ACM Awards. The "You're Easy On the Eyes" singer paired a rich brown snakeskin leather jacket with sleek black leather pants, a simple V-neck tee and shiny black boots while also rocking two must-haves from the '90s: a choker and a very Rachel-from-"Friends" haircut.

Best song nominees Kix Brooks and Ronnie Dunn of Brooks & Dunn let their jackets do the talking at the 1999 ACM Awards. While Kix, donning his signature black cowboy hat, went bold in a royal blue sports coat, Ronnie opted for a more tailored look in this embroidered black blazer. Paying homage to their country roots, both gents paired their looks with denim, oversized belt buckles and leather boots.

Singer-songwriter Sara Evans was glowing at the 1999 ACM Awards. The "Cryin' Game" singer, who was six months pregnant at the time, adorned her voluptuous frame in a metallic blue empire-waist gown with a sheer black polka-dot overlay.

We're not exactly sure what look Naomi Judd was going for at the 1999 ACM Awards. Wearing a sheer black high-collared cheongsam-inspired gown with intricate gold embroidery, Naomi confusingly paired the dress with a wrinkled black shawl and a messy, flower-adorned updo.

Musician Charlie Daniels and wife Hazel Daniels prove age isn't an impediment to style. Charlie — a renowned multi-instrumentalist known for hits like "The Devil Went Down to Georgia" and "Long Haired Country Boy" — kept his 1999 ACM Awards look classic with a pinstriped suit and wide-brimmed cowboy hat. Hazel complemented her beau's look with a fitted cobalt blue pantsuit and matching satin heels.

We love Jo Dee Messina but wish someone would have talked her out of this awkward-fitting prom dress at the 1999 ACM Awards. Jo Dee — who was nominated for best album along with Tim McGraw as well as best new female vocalist (the latter of which she won) — wore this sleeveless satin lavender gown with silver trim that under-emphasized her amazing figure and unfortunately clashed with her vibrant red hair.

Actress-singer Crystal Bernard arrived at the 1999 ACM Awards with country music star Billy Dean. Wearing an iridescent organza gown with a tied waist and layered skirt, Crystal looked radiant next to Billy, whose collarless Nehru suit emphasized his incredibly broad shoulders. The duo began secretly dating in 1997 after meeting on the set of Crystal's TV series "Wings."

Pop and country music icon Patti Page was the picture of elegance on the 1999 ACM Awards red carpet. Wearing a flowing black maxidress with a long-sleeved lotus-adorned overlay, Patti proved that even after 50 years in the music industry, she still knew how to steal the spotlight.

Is it us or does Lila McCann look extremely excited to be at the 1999 ACM Awards? Wearing a medieval-inspired indigo dress that featured a corseted waist, asymmetrical skirt and lace inserts, the 17-year-old "I Wanna Fall in Love" singer wasn't shy about her enthusiasm on the red carpet.

Singer Bryan White and then-girlfriend (now-wife) actress Erika Page arrived on the red carpet in matching all-black styles. While Bryan looked buttoned-down in a double-breasted suit, Erika stunned in a strapless black dress featuring a thigh-high slit, which she paired with floral embellished peep-toe heels.

Country singer Chely Wright invoked the spirit of everything we loved about '90s red carpet fashion. Wearing a soft pink micro-fringed asymmetrical skirt and a sheer, tummy-baring half-sleeved crop top, Chely was working some serious pre-millennium style.

It's not that we don't like Oscar-nominated singer-songwriter Allison Moorer's dress from the 1999 ACM Awards… it's just that we wish she wore something as vibrant and beautiful as she is. The "A Soft Place to Fall" singer played it safe on the red carpet in a shapeless floral-embellished black shift dress paired with black sandals and a matching handbag.

Here's how you go all-black on the red carpet and still have fun. Singer Janie Fricke got playful with her 1999 ACM Awards style in this Mandarin-collar jacket worn over a black mini with matching leggings and rhinestone-studded black boots. The "Down to My Last Broken Heart" singer added a black cowboy hat and glittering globe handbag to complete her look.