Grammy Favourites: Caribbean Presence, Front and Centre

Grammy night usually starts the same way for us all: phones out, group chats buzzing, volume a little too loud, arguing over who looks good before the show even really begins. We’re watching from home, clocking the fits, clocking the energy, and, let’s be honest, looking to see who showed up for the Caribbean!

And this year? The presence was loud. Proud. Undeniable!

Bad Bunny remains one of the clearest examples of what it looks like to take Caribbean culture global without watering it down. From Puerto Rico to the world, his music, delivery, and personal style always feel intentional, whether that shows up through bold tailoring, unexpected proportions, or moments that challenge what men’s fashion is “supposed” to look like. 

He once again stole the spotlight, not just with his music but with his style and presence on the global stage. At the 2026 Grammys, he walked the red carpet in a custom Schiaparelli haute couture tuxedo,  marking the first-ever major menswear look from the famed house on a red carpet, blending classic tailoring with avant-garde detail. The black velvet ensemble featured a cinched waist, dramatic shoulders, and corset-like lace-up detailing on the back, all rooted in couture craftsmanship while still feeling distinctly his own.

What makes it even more powerful is what he did with his voice. When accepting the night’s biggest honour  – Album of the Year for DeBÍ TiRAR MáS FOToS – he delivered much of his speech in Spanish, celebrating Puerto Rico, his culture, and the global Latino community. Starting with “Puerto Rico” and speaking directly to experiences that resonate across the Caribbean and beyond reminded everyone watching that representation on this stage is about so much more than awards, it’s about identity, pride, and belonging.

Jamaica’s own Lila Iké reminded us that strength doesn’t have to be aggressive to be powerful. As the only woman to be nominated in the reggae category, her presence alone carried weight – and she wore it with elegance and intention. Her gown, a custom piece by Halil Ülgü, was a striking shade of blue, a thoughtful nod referencing her nominated album Treasure Self Love. The structured bodice with a shimmering, almost wet-look finish gave the dress a modern, sculptural edge, while the movement of the fabric mirrored her calm, grounded energy. 

Styled by Ivy Coco, who also carries Jamaican roots, every element of her look reflected artistry; the moment felt deeply aligned, women supporting women, culture meeting care. Lila’s presence was storytelling in motion: expressive, confident, and fully in control of her narrative, celebrating Jamaican heritage and reminding Caribbean women everywhere of the power in believing in yourself, and showing up unapologetically.

For the 2026 GRAMMYS Premiere Ceremony opening performance of “Shining Star”, Lila OPENED the performance, bringing an infectious energy. Her outfit, styled by Posh McKoy, was a tiered, beaded number designed for movement and impact, paired with a statement fur coat that fused elegance and “gangsta” attitude, a perfect reflection of her bold stage presence. The whole outfit came together to create a look that was dramatic and celebratory. Every twirl of the dress and sweep of the coat highlighted the rhythm of the performance, giving Lila a stage-ready presence that was as commanding as it was graceful.

Many people may not even realize that Olivia Dean carries Caribbean roots, but she made sure to honour them on one of music’s biggest stages. Accepting her Grammy for Best New Artist, Olivia spoke about being the granddaughter of immigrants, with those roots tracing back to Jamaica and Guyana; what a powerful acknowledgment of the journeys that made her moment possible! She is the Woman We Need!

On the red carpet, Olivia arrived in a truly showstopping custom black‑and‑white Chanel gown by Matthieu Blazy, a look that felt both classic, playfully modern, and aligned with her brand image. The dress featured a black sequin bodice that shimmered under the lights, a full ivory satin skirt with a dramatic sweep, and a striking band of black feathers at the waist that added movement and texture to the silhouette. Paired with matching black‑and‑white Chanel heels and sparkling diamond jewelry, her ensemble evoked old‑school glamour while feeling strikingly of the moment.

For her performance of Man I Need during the ceremony, Olivia switched into a red Chanel mini dress embroidered with camellia flowers and trimmed with feathers, a bold contrast that brought warmth and energy to her stage presence. The shorter silhouette, vibrant colour, and playful detailing mirrored her dynamic performance style and artistic confidence, turning her fashion into another form of storytelling.

Both looks spoke to her artistry, blending refinement with expressive joy, and showcasing style that evolves with her image and music. In every moment, Olivia carried her heritage, her voice, and her unique perspective forward, proving that presence, pride, and personality can shine just as brightly as any red‑carpet gown.

Lola Young, born in the U.K. with mixed Jamaican-Chinese heritage, brought a layered cultural presence to the 2026 Grammys! Although many viewers may not immediately know her background, her artistry and style should’ve been a sure-fire sign that she had Caribbean roots! She brought something raw and expressive to the carpet. Her fashion, much like her music, doesn’t feel polished for approval, it feels extremely honest. She arrived in full Vivienne Westwood, wearing a look from the designer’s Spring/Summer 2025 collection that featured trinkets printed in monochromatic halftone, creating an abstract camouflage. Nominated in the Best New Artist category, Lola has been breaking through in a major way, especially with her 2025 hit Messy, the most downloaded song in the U.K. Her outfit mirrored that same boundary-pushing spirit: playful, expressive, and confident, a visual echo of her music. Lola’s presence reminded viewers that fashion, like art, is storytelling; a way to declare your individuality while honoring where you come from.

The 25-year-old singer took home her first Grammy on Sunday for Best Pop Solo Performance with her hit song Messy. Her acceptance was a beautiful celebration of authenticity, of unapologetic self-expression. There’s a freedom in that, and it’s refreshing to see artists embracing individuality rather than chasing perfection.

Keznamdi brought a humble, yet confident energy to the Grammys that felt unmistakably rooted in Jamaica. “We a represent Jamaican culture!” he said, as the recording artist took home the Grammy for Best Reggae Album on Sunday for his 13-track set Blxxd and Fyah, a milestone that cemented his influence on the global stage. For the occasion, he wore a full white suit, tailored with clean lines that radiated a sense of elegance and understated royalty – a nod to the regal pride often celebrated in Jamaican culture. On his feet, he paired the look with classic Clarks Wallabees, a subtle but meaningful connection to the footwear many Jamaicans grew up wearing, turning everyday roots into a statement of heritage. Keznamdi’s ensemble mirrored his music: grounded, authentic, and steeped in “truths and rights”. Every detail, from suit to shoes, was intentional, a reminder that success and style can carry culture proudly to the world.

What stood out most wasn’t just what people wore, it was who they showed up as. Caribbean artists continue to bring their full selves to global stages, unapologetically, with pride and personality.

And watching from home, that’s what makes us sit a little straighter, turn up the volume, and say,

 “Wi likkle but wi tallawah!”