Chlöe Bailey Brings Tailored Edge to Milan with BOSS

Chlöe Bailey turned to sharp tailoring for her Milan appearance with BOSS, leaving behind the red-carpet gowns for a more structured look. The singer shared photos on Instagram wearing an oversized black blazer layered over a white shirt and finished with a striped tie. The styling leaned into classic menswear while still feeling modern and personal.

Photo: @chloebailey-Instagram

She paired the blazer with sheer black tights, pointed stilettos, and a compact handbag. The accessories were kept minimal. Clear aviator-style glasses added a whimsical element, matching the caption she wrote alongside the post: “your favorite nerd out in Milan with @boss thank you for taking good care of me milan.”

Photo: @chloebailey-Instagram

The blazer’s broad shoulders and boxy cut gave it presence, balanced by the clean white shirt cuffs peeking out at the wrists. The short hemline revealed just enough of the shirt beneath, breaking up the dark palette and keeping the look from feeling too heavy. It struck a balance between structure and ease, giving the outfit personality without looking stiff.

Her hair, styled in neat shoulder-length twists, and understated makeup kept the attention on the tailoring and accessories. Every element supported the clean lines of the look.

Photo: @chloebailey-Instagram

The outfit echoed BOSS’s long-standing focus on power dressing but avoided being overly formal. By swapping trousers for tights and heels, Bailey turned the classic suit combination into something more playful and fashion-forward.

For BOSS, it was another example of how the brand’s tailoring connects with younger audiences. For Bailey, it marked another confident step in her fashion journey. It shows she can move easily between music stages, film sets, and the front rows of Milan.