The 5 Most Charming Moments From Olivia Dean’s Tour

Just nine months ago, Olivia Dean opened for Sabrina Carpenter at Madison Square Garden during the Short n’ Sweet tour. Less than a year later, she’s sold out four consecutive shows at the historic New York City arena from Aug. 15 through Aug. 18. The Art of Loving Live Tour supports her sophomore album, while also featuring some of her older songs, acoustic renditions, epic outfit changes, moody upholstered backdrops, powerhouse backup vocals, and tons of heartwarming advice.

Dean’s album, The Art of Loving, is predicted to be a contender in major categories during the 2027 Grammys and focuses on love in all of its forms: self-love, romantic, platonic, and love lost. During her show, the neo-soul singer introduces each track by explaining why she wrote it. For example, to “remind you you’re that b*tch” for “So Easy (To Fall in Love)” or an ode to her grandmother, who immigrated to the U.K. from Guyana at just 18 years old, before “Carmen.”

Ahead of the third sold-out show at MSG on Aug. 17, I went to the Olivia Dean activation at UMusic Shop NY to check out the curated experience and exclusive merch. There were photo ops, exclusive vinyls, a lush cheetah-print carpet, and several styles of New York-specific T-shirts and merch. I went with a black tee that says “New York Is For Lovers” on the front, with the tour name in the back — and spotted tons of fans wearing pieces from the exclusive collection by the time I got into the venue.

Read on for a rundown of the show’s most charming moments, from outfit changes to disco dance party vibes.

Silhouette Singing & A Curtain Drop

Just like the tour’s namesake album, the concert aptly started with “The Art of Loving (Intro).” Like many superstars before her, Dean had fans on the edge of their seats as she sang behind a curtain. Her silhouette was projected by a spotlight while she sang the intro, which is less than a minute long, before the curtain dropped to reveal her first look — a form-fitting black gown.

Shouting Out Bell Hooks (Twice)

As she introduced each song, Dean shared what inspired her lyrics. At one point, she spoke sweetly about how much she loves bell hooks’ All About Love: New Visions, and encouraged everyone in the audience to read it if they haven’t. She shared a quote from the book about how love is about wanting a person to be the best version of themselves before going into “Let Alone The One You Love.”

Before the show ended, she revisited her love for bell hooks, saying if she wanted fans to take on thing from her show besides having a good time, it would be to read that book.

A Whimsical Second Look For The Second Stage

The art of an outfit change is a beautiful thing, and while the brass band played upbeat solos, Dean hurried off-stage to get ready for her stint on the second stage further back on the floor. The stage was shaped like a flower, and when she reemerged, you could see that the layers of her full skirt mimicked petals too.

A Third Outfit Change & Disco Vibes

After a few slower-paced songs on the second stage, Dean made her way back to the main stage and once again switched to a new look. This time, it was a bedazzled cheetah-print corset-top dress with a flirty fringe skirt. Simultaneously, four huge disco balls were erected in all four corners of the floor. This created a complete disco dance-party vibe as she sang “Baby Steps” while lights bounced all over the arena.

A Confetti Blast During “Man I Need”

Fans were waiting with bated breath to hear the hit song “Man I Need,” so it was only fitting that Dean saved it for the very last song of the night. While vibes were at their highest, everyone was on their feet, and the residual hype from the disco ball moment was still intact — the familiar beat started. The grand finale included an epic confetti blast, with pieces reading lyrics like “love’s never wasted” and “when it’s shared,” that showered over the euphoric audience.