Jessica Chastian’s TIFF styles: on point or off the mark?

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All of us here at Celebitchy are fans of Jessica Chastain as an actress. As a fashionista, she’s been more on the “miss” side than the “hit” side. I mean, who could forget the light blue Calvin Klein gown she wore for the Golden Globes that did nothing for her? And what of the tragic “shelf boobs” that were on display in an otherwise gorgeous Armani gown at Cannes back in May? But, credit where credit is due, it hasn’t been all fashion fails for Jessica. She did dazzle in a beaded purple Givenchy gown at Cannes. And now, the 40-year-old-actress made it to the “do” list with her fashion choices at the Toronto International Film Fest this past weekend.

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It’s almost a fashion given that redheads look good in red, and Jessica was definite proof of this in a fiery red spaghetti strap gown by Zuhair Murad. She accessorized with pink sapphire and diamond earrings from Piaget and Christian Louboutin heels. I love the elegant simplicity of the gown and her hair’s subtle waves and matching red lipstick make her look absolutely radiant. Jessica was dolled up for the premiere of her new movie Woman Walks Ahead on Sunday and posted a hilarious pic to Instagram holding up cardboard cutouts of her head with the caption, “Ugh, that Chastain chick is everywhere.”

Ugh that Chastain chick is everywhere @tiff_net #WomanWalksAheadPremiere

A post shared by Jessica Chastain (@jessicachastain) on

Also during the TIFF festivities, Jessica hit the red carpet for the premiere of Molly’s Game (written by Aaron Sorkin, in which she stars as a woman running a high-stakes underground poker ring) in a stunning blue gown from Prada. She’s already proven that blue definitely works for her, although her boobs looked like they were crying out for at least a tiny bit of underwire in the Elie Saab dress she wore to the Spirit Awards earlier this year. This time, the girls looked much happier and Jessica’s pulled back ‘do and perfect makeup showcased her flawless face.

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Jessica showed off another creation from Elie Saab, a black print cocktail-length at an event hosted by HFPA and InStyle. I’m not big on prints, and the flared out skirt is something I’m not a fan of, but it fits Jessica well and her hair and makeup look wonderful.

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And, going four for four for the weekend, Jessica wore a simple yet sophisticated gold Oscar De La Renta dress to Entertainment Weekly’s Must List Party. Gold tones also suit Jessica’s pale skin and red hair quite well. It’s a little too “mother of the bride” for my taste, but it looks like it was made for the actress. Way to keep the Fashion Police at bay, Jessica!

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42nd Toronto International Film Festival - Molly's Game - Press conference

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19 Responses to “Jessica Chastian’s TIFF styles: on point or off the mark?”

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  1. Sara says:

    Talented beautiful lady. Her fashion to me is secondary because she brings a lot to the table.

  2. midigo says:

    Gorgeous woman.
    She is much better in motion than in still.

    • Imqrious2 says:

      She looks gorgeous, though personally, I’d like her to darken her brows a schooch to emphasise her beautiful eyes.

      Love all the outfits: the red is stunning, and the teal color is perfect for her skin tone. I like the playfulness of the black dress. The gold is meh: blends too much with her skin. Perhaps with a different shoes, neckline, some bold jewellery to break it up, no sleeves or bracelet length sleeves…?

      Anyway, gorgeous, talented woman!

  3. Snazzy says:

    I really like the black Elie Saab

  4. Astrid says:

    She’s gorgeous but those outfits don’t seem right for her

  5. Maria F. says:

    i like all the looks, but the Ellie Saab. I am not a fan when the underlinings are not as long as the dress itself.

  6. Serene Wolf says:

    I love the red dress.❤

  7. Amelia says:

    She always has bust issues. I feel like we need to accept that for whatever reason, her girls sit differently and that doesn’t translate into gowns. I’m really not trying to be mean, just always seems like her bust is the only thing problematic with her looks.

  8. Heat says:

    Molly’s Game was awesome! Powerhouse performances from Jess and Idris, and her boobs have never looked better (Molly wore a lot of low cut dresses)! Sorkin introduced the film, and I know he’s an ass but he was quite charming and had lovely things to say about Toronto crews. Called it a “Sorkin talkie”.

  9. Laura says:

    She looks fantastic! In all of the outfits except the gold dress. That’s not my cup of tea.

  10. bitchyarchitect says:

    Is Aaron Sorkin going to the same tanning salon as Sean Penn. Talk about hamhock.

  11. bella says:

    Love all the outfits! She is a great actress and just so beautiful!

  12. meh says:

    You can just see right through that red dress, can’t you.

  13. Aredheadforreal says:

    what are you talking about ” a fashion given?” I remember my older, also ginger sisters telling me i am forbidden from wearing red/pink/orange growing up. While i have since become more open to the hue, its by no means a fashion given the way that green is for us. I dont know which redheads you have been taking to….