From glamorous ESPYS gowns to bold Chicago Bears game-day fashion, Biles brings championship confidence to every appearance.
Simone Biles has spent years making the extraordinary look effortless, and that same confidence follows her well beyond the gymnastics floor.
Whether she is stepping onto an awards-show carpet or supporting the Chicago Bears from the sideline, the Olympic icon brings a playful, polished sense of style to every appearance.
These 10 looks show Biles moving easily between sweeping gowns, memorable Derby fashion and unforgettable game-day statements.
1. Golden glamour at the 2026 ESPYS
Biles opened a new style chapter in a champagne-gold satin gown with a sculpted bodice, dramatic skirt and sweeping train. The luminous color and elegant silhouette made it an immediate cover-worthy moment.
2. Metallic shine at the CMA Awards
At the 2024 CMA Awards, Biles chose a sleek one-shoulder metallic gown that caught the light from every angle. The fitted silhouette and minimal accessories kept the focus on the dress’s liquid-silver finish.
Her 2025 ESPYS gown blended deep blue and purple tones in a curve-skimming, shimmering design. The rich color and structured neckline delivered a classic red-carpet moment with plenty of personality.
Biles embraced Derby tradition in a strapless lavender minidress and coordinating wide-brim hat. The soft color, playful length and delicate details made the outfit feel fresh without losing the event’s polished spirit.
On a cold Chicago sideline, Biles paired a fluffy white coat with bright orange custom Bears pants and pointed white boots. It was warm, team-forward and impossible to miss.
Biles made a dramatic entrance in a full-length graphic coat, white gloves and black lace-up boots. The oversized print gave the playoff outfit a bold, editorial edge.
For the Bears’ wild-card game, Biles wore a floor-length dark coat accented with team-inspired details and a matching No. 36 bag. The dramatic outerwear brought glamour to a snowy football night.
At the Barnstable Brown Derby Eve Gala, Biles mixed an ivory corset-style top and shorts with black tights, pointed heels and a whimsical headpiece. The contrasting pieces made the look playful, modern and perfectly suited to Derby weekend.
Biles leaned into football fashion with an oversized Bears varsity jacket, slim black pants and tall lace-up boots. The orange-and-navy jacket carried the outfit while the streamlined base kept it sharp.
An oversized denim jacket and matching jeans gave Biles a relaxed game-day uniform for the Bears-Vikings matchup. Dark sunglasses and a tiny No. 36 handbag added just enough star power to the casual look.