Jessica Chastain went with a cozy but chic look for her latest outing.
The Oscar-winning actress spent her Thanksgiving morning in New York City attending Macy’s Thanksgiving Day Parade. She watched performances by Cynthia Erivo, Ciara, Lainey Wilson, Jewel, and more.
Jessica Chastain attends the Macy’s Thanksgiving Day Parade 2025 at Macy’s Herald Square on November 27, 2025 in New York City.
Getty Images for Macy’s
For the event, Chastain wore a classic style of footwear. She slipped into leather Chelsea boots from Brunello Cucinelli with a structured pointed toe that met in a slight square. Her brown boots featured a low heel that boosted Chastain up a few extra inches.
A closeup of Chastain’s boots.
Bryan Bedder
Ankle boots like Chastain’s are a popular choice for the fall and winter seasons since they can offer a little more coverage for the cold months while still adding a stylish touch to any outfit. They’re also very versatile, and can be styled with nearly all wardrobe essentials, from skirts and dresses to trousers and denim.
Jessica Chastain attends the Macy’s Thanksgiving Day Parade 2025 at Macy’s Herald Square on November 27, 2025 in New York City.
Getty Images for Macy’s
The “Eyes of Tammy Faye” star paired her boots with a cream mostly monochrome outfit. She wore cream trousers with a high waisted rise. She paired the pants with a crisp white button down blouse. Chastain added a white cardigan over the top with a chunky knit and brown pattern throughout. She accessorized the outfit with a brown leather belt that coordinated with the color and material of her boots.
The star is known for her stylish outfits, both on and off the red carpet. For her footwear, she tends to wear silhouettes like trendy strappy sandals, towering platforms, and sleek pointed toe pumps from top brands like Gucci, Stuart Weitzman, Christian Louboutin, and more.
