Day: November 16, 2025

He walked the red carpet that year in skinny blue jeans, a black belt with a red horseshoe buckle, and a multicolored vest that matched his blazer.

The top of his outfit was, for the most part, red-carpet ready. He only needed a button-up top beneath his vest.

When paired with jeans, though, the outfit didn’t make sense. The bottom half was too casual for the event.

He was photographed at the 37th annual CMA Awards wearing light-wash jeans, dark cowboy boots, a black button-up shirt, and a brown suede jacket.

The outfit, which he completed with a cowboy hat, wasn’t bad by any means — but it also wasn’t the most memorable choice for country music’s biggest night.

The country legend performed that year while wearing bell-bottom jeans adorned with gold sparkles and white lace. There were also gold chains and a heart-shaped charm placed across one pocket.

Parton’s pants were standouts on their own. However, the outfit was perfected with a form-fitting top that had sharp shoulder pads, a lace waistband, and gold embellishments.

KaufmanFranco designed her sleeveless gown, which fit her like a glove. It was decorated with small reflective pieces and had a V-shaped neckline with sheer straps.

The floor-length dress remains one of Swift’s best red-carpet looks of all time.

She hit the red carpet in a sleeveless minidress that was covered from top to bottom in blue sequins. The vibrant choice looked great on the musician and complemented her signature red hair.

Unfortunately, her shoes weren’t the right choice. Simpler silver heels with thin straps would have looked better and matched her delicate earrings.

She wore a baby-pink Oscar de la Renta gown with short sleeves, a mesh neckline, and all-over silver sparkles. Although the dress was pretty, it was somewhat dated.

Her retro hairstyle also distracted from its glamour. A classic updo would’ve made a huge difference.

She wore a sheer silver gown with a plunging neckline and dramatic, puffed sleeves. The music icon also opted to wear layered pearls and diamond necklaces.

Beyoncé wore the dress, which was both elegant and bold, for a performance with The Chicks.

He walked the red carpet in skinny trousers, a fitted blazer, and a black shirt with a floral print. For shoes, he chose navy boots in a dark blue shade.

Though the outfit was understated, it was effective. He stood out from other musicians who wore plain black tuxedos on the carpet.

The country star arrived at the CMA Awards that year wearing a plum-colored suit with black lapels and a matching handkerchief. He also wore a black, button-up shirt.

The suit looked sharp on him and was simple enough to highlight his wife’s gown. Nicole Combs wore a long-sleeved, floor-length dress decorated with silver sequins.

Jean-Louis Sabaji designed her metallic dress. It had a single sleeve with an exaggerated shoulder, a mesh bodice and skirt that were completely sheer, and a mix of gold and silver fringe across the gown.

Though the outfit was fun, it was a bit too over-the-top for Underwood’s petite frame. She wore it with silver platform heels and statement earrings.

She wore a vintage Thierry Mugler design that comprised a pink satin gown beneath a black lace overlay.

The two pieces would have been pretty on their own, but together, they clashed.

Christian Siriano designed her baby-pink look, which had an asymmetrical neckline, a wrapped bodice, and a floor-length skirt with a thigh-high slit.

Its light color paired perfectly with the country singer’s blonde hair and red lipstick.

She wore a black blazer with sections of sparkles, a satin blouse, a silver bolo tie, and a cowboy hat that night.

She also added a daring touch: see-through pants. The outfit was simple, exciting, and true to Wilson’s style.