The Coolest Looks Of The Week, From Chappell Roan To Rihanna

From fabulous frocks to the best front-row fashion, the best celebrity style this week.

VMAs! Fashion week! Toronto Film Festival! Tennis! Buckle up. After a couple of weeks’ hiatus, we’re back with a big one.

Chappell Roan

The incomparable Chappell Roan in the best outfit from the MTV Video Music Awards. Evocative of Aubrey Beardsley, this Y/Project look with Juniper Rose chainmail gloves was styled by Chappell’s regular collaborator, Genesis Webb. Her on-stage look (Rabanne) was also fabulously theatrical — really, we expect nothing less.

Ciara

A great ensemble for the Willy Chavarria show at New York Fashion Week; plaid on plaid on plaid with snazzy white shoes.

Selena Gomez

Loving this pivot from Selena, who’s been wearing a lot of black lately; the Gothic glamour suits her well. This one is Rodarte. There was another look at the festival, high-necked and maribou-trimmed Saint Laurent, like Valley of the Dolls but darker.

Chloë Sevigny

Classic Chloë, this calls to mind her pivotal early 2000s looks — fitting for a namesake event in New York City.

Da’Vine Joy Randolph

Very Grecian goddess in this statuesque gown by Christian Siriano. Styled by Wayman Bannerman and Micah McDonald, the Oscar winner is at the Creative Arts Emmys.

Damiano David

Måneskin frontman stepped out in a more conservative look than usual at the VMAs. It’s Etro, and Damiano looks fabulous.

Maya Rudolph

More draping, this time on Maya, who’s wearing Chloé by Chemena Kamali, styled by Rebecca Grice.

Kendall Jenner

This is the best look we’ve seen on her in a while, I wish she leant into this whole 1990s supermodel thing more. Fittingly for that vibe, Kendall — who made a bit of a splash with the new Marni campaign this week — is wearing an archival Manfred Thierry Mugler skirt suit from Aralda Vintage. Styled by Dani Michele, the accessories are what really help carry this one home; a stiff little bag (The Row) and some almond toe pumps.

Cate Blanchett

Gorgeous Givenchy (from 2019) styled by Elizabeth Stewart.

Michelle Williams, Jodie Turner-Smith and Elizabeth Olsen

Dressed for the front row at Tory Burch, this trio look brilliant. Tailored and tidy. Great shoes.

Leon Bridges

After witnessing so many Hollywood men wearing oversized jackets for so long, it’s a nice palate cleanser to see Leon Bridges step out in this snug number. This look, styled by Gabriela Tena (it’s Khaite) works because the pants — great cut — hit high.

Paris Hilton

This self-referential ensemble (custom Celia Kritharioti, an Athens-base couture band that was founded way back in 1906 apparently) at the VMA’s calls back to the star’s famous 21st birthday outfit.

Demi Moore

Another great tie look from this week. Demi is wearing Thom Browne to Toronto Film Festival, where she’s promoting The Substance (I saw it last week and it’s bananas, in a good way, but not for the faint-hearted).

Cyndi Lauper and Lil’ Kim

Also wearing Christian Siriano this week were these music icons, who attended the designer’s New York Fashion Week show.

Sarah Paulson

A sublime Simone Rocha look on Sarah Paulson. Styled by Karla Welch, the actor is also wearing Gianvitto Rossi shoes and Anabela Chan jewellery, with a clutch (I miss these) by Roger Vivier.

Christine Baranski

A very sharp Thom Browne ensemble on the legendary actor, who’s at a preview of the designer’s spring-summer 2025 collection at The Commerce Inn in the Big Apple.

Rihanna

No notes. Never any notes.

Emma Gleason is the Herald’s deputy editor of lifestyle and entertainment (audience), and has worked on Viva for more than four years, contributing stories on culture, fashion and what’s going on in Auckland.

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