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Tessa Thompson in Schiaparelli

Mandatory Credit: Photo by Matt Baron/Shutterstock (12869705hj) Tessa Thompson Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is obviously VERY bold, albeit quite in her wheelhouse. The giant collar is very striking. (The bike shorts are, of course, ridiculous.)

Julia Fox

Mandatory Credit: Photo by Broadimage/Shutterstock (12870115bs) Julia Fox 2022 Vanity Fair Oscar Party in Beverly Hills, California, Los Angeles, USA - 27 Mar 2022

Yes, the turtleneck is a hand that is...well, if not choking her, lightly cradling her thyroid. All seems in order, here.

Janelle Monae in Christian Siriano

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874ca) Janelle Monae Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Christian Siriano Same Outfit as Catwalk Model *12438402bo

Oh lordy. I love her, and Siriano is a treasure, but the idea of trying to sit in this makes me get sympathy hives, and I feel like this must look dangerous in motion. I wish the skirt were solid, at least. (Her head looks great, of course.)

Rosario Dawson

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874sj) Rosario Dawson Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is VERY voluminous and extremely 80s but it's also...visually interesting?

Paris Jackson

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874vr) Paris Jackson Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is similarly voluminous and perhaps even MORE '80s. I love it?

Saweetie in Etro

Mandatory Credit: Photo by Broadimage/Shutterstock (12870115bj) Saweetie 2022 Vanity Fair Oscar Party in Beverly Hills, California, Los Angeles, USA - 27 Mar 2022

This is risky in the sense that she is trusting that fabric with her life! Having said that: This hair and makeup situation is so pretty on her. What a dish!

Zazie Beetz in Monot

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768yd) Zazie Beetz Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Monot

Red hose aside, this is not THAT bold...

Zazie Beetz in Monot

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768yc) Zazie Beetz Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Monot

...until you see the side view!

Dakota Johnson in Gucci

Mandatory Credit: Photo by Casey Flanigan/imageSPACE/Shutterstock (12869708h) Dakota Johnson Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

And this is bold in the sense that it is HUGE and MEMORABLE.

Dakota Johnson in Gucci

Mandatory Credit: Photo by Matt Baron/Shutterstock (12869705am) Dakota Johnson, wearing Gucci Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This feels like a ceremony gown to me. I LOVE it.

Laura Harrier in Off-White

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874kr) Laura Harrier Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Off-White Same Outfit as catwalk model *12826863cf

And this is a big statement only in the sense that I'd like to use a MASSIVE FONT SIZE to note how GREAT IT IS. It's FANTASTIC.

LaKeith Stanfield

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768jd) LaKeith Stanfield Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This rather looks like a referee whose game went into triple OT and he didn't have time to go home and change before his friend's birthday, so he just threw on a dramatic coat and hoped for the best on the way to the club.

Hannah Einbinder in One/Of

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768kt) Hannah Einbinder Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is admittedly in her wheelhouse. She looks great AND like she's playing a Young Holland Taylor in something.

Dan Levy

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768li) Dan Levy Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

I think my big note here is that I wish his trousers were slightly less drapey, material-wise.

Jack Quaid

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768xw) Jack Quaid Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

SNAZZY! He's Dennis Quaid and Meg Ryan's son, and this is the first time he's really looked like his mother to me.

Maria Bakalova in Giambattista Valli

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768ns) Maria Bakalova Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

Okay, this isn't that risky but it's maybe a teeny bit bold and we're here now. I like this except it also reminds me of a nightgown.

Donald Glover in King & Tuckfield

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768ce) Donald Glover Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing King & Tuckfield

He can truly wear almost anything.

Kim Kardashian in Balenciaga

Mandatory Credit: Photo by Matt Baron/Shutterstock (12862768kg) Kim Kardashian Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Balenciaga

This look is NOT designed to blend in. I like it -- although I alway think a train at this event is ill-advised.

Hunter Schafer in Rick Owens

Mandatory Credit: Photo by Casey Flanigan/imageSPACE/Shutterstock (12863280kx) Hunter Schafer Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Rick Owens Same Outfit as catwalk model *12831335s

This is also very in her wheelhouse but my conscience would not allow me to place a Rick Owens dress in the "safe" category.

Olivia Culpo

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874na) Olivia Culpo Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is just primarily HUGE! But fun -- the color is great.

Jay Ellis

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874sv) Jay Ellis Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

This is foxy.

Aldis Hodge

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874ud) Aldis Hodge Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

Also foxy.

Normani

Mandatory Credit: Photo by Matt Baron/Shutterstock (12869705q) Normani Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

Honestly, also foxy, but I wish the underpinnings were also black.

Anya Taylor-Joy

Mandatory Credit: Photo by Matt Baron/Shutterstock (12869705re) Anya Taylor-Joy Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

I technically think the dress is somewhat dull. We've done it, you know? But the veil over her face is going for something, anyway. I appreciate it.

Kelly Rowland

Mandatory Credit: Photo by Broadimage/Shutterstock (12870115ag) Kelly Rowland 2022 Vanity Fair Oscar Party in Beverly Hills, California, Los Angeles, USA - 27 Mar 2022

These are some SLEEEEEEVES!

Daisy Edgar-Jones in Versace

Mandatory Credit: Photo by David Fisher/Shutterstock (12868874ka) Daisy Edgar-Jones Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022 Wearing Versace Same Outfit as catwalk model *12822487bi

I LOVE this. It's unusual, certainly, but fantastic on her.

Poppy Delevingne in Christopher Kane

Mandatory Credit: Photo by Broadimage/Shutterstock (12870115eq) Poppy Delevingne 2022 Vanity Fair Oscar Party in Beverly Hills, California, Los Angeles, USA - 27 Mar 2022

If cornhole were a dress! (It's fun though.)

Donatella Versace

Mandatory Credit: Photo by Matt Baron/Shutterstock (12869705lq) Donatella Versace Vanity Fair Oscar Party, Arrivals, Los Angeles, USA - 27 Mar 2022

Listen, sometimes this woman knows what she's doing.

Some Folks Really Swung for the Fences at the Vanity Fair Party
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