![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6782/160721_winona_ryder_78069152.jpg)
Look 1: The Pink Sweater
GRAMMY Awards after party ’89
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6774/160721_winona_ryder_114949317.jpg)
Look 2: The Corset Jacket
Dracula premiere ’92
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6779/160721_winona_ryder_116121154.jpg)
Look 3: The Velvet Slip Dress
Dave Pirner & Winona ’93
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/2016/07/160721_winona_ryder_114949262.jpg)
Look 4: The Mum Jeans
The Commitments premiere ’91
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6777/160721_winona_ryder_155502253.jpg)
Look 5: The Kid’s Travel Bag
LAX airport ’90
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6771/160721_winona_ryder_75458439.jpg)
Look 6: The big bow
Costume Institute Gala ’07
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6767/160721_winona_ryder_156185715.jpg)
Look 7: The Bridal Dress
Matt Damon & Winona at the Golden Globes ’07
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6773/160721_winona_ryder_114949816.jpg)
Look 8: The Low-Cut Bodice
Attending an awards night ’96
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6776/160721_winona_ryder_78478836.jpg)
Look 9: The Johnny Depp Arm Candy
Cry-Baby premiere ’90
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/media/6778/160721_winona_ryder_86001655.jpg)
Look 10: Twinning with Gwenyth
Winona & Gwenyth Paltrow ’90
![](https://www.marieclaire.com.au/wp-content/uploads/sites/5/2016/07/160721_winona_ryder_488828532.jpg)
Look 11: All Black Everything
Marc Jacobs Spring 16 runway show