Kate Winslet’s Shoes Looked So Comfy, We’re Carving Out Space for Chelsea Boots in Our Fall Closet

Kate Winslet’s recent fall footwear choice was a jackpot. 

On September 24, the Titanic actress was spotted in New York City wearing a pair of Chelsea boots, the classic shoes everyone needs to have on their radar. They came in a rust-like brown color and had stretchy elastic on the sides — a distinguishing mark of the style — which perfectly matched her slouchy blazer. 

Also seen on Jessica Alba and Gwyneth Paltrow, Chelsea boots have already been around throughout all of 2024. But as it’s now fall, warm and comfortable styles are especially vital. Plus, they’re frequently flat and easy to walk in, they take zero time to lace up, and they look stylish when worn under or tucked into bottoms. 

Oprah, along with other celebrities, have also sported the posh and preppy shoes, so we found seven Amazon pairs for under $55 for you to swoop in on the trend, too. 

Chelsea Boots Inspired by Kate Winslet 

• Dream Pairs Chelsea Boots, $34 with Prime (orig. $43)
• Mysoft Chelsea Boots, $31 with coupon and Prime (orig. $46) 
• Dr. Martens Embury Leather Chelsea Boot, $90–$120 (orig. $130) 
• Hawkwell Chunky Chelsea Boot, $31 (orig. $60) 
• Vepose Chelsea Boots, $42 with coupon (orig. $50) 
• Steve Madden Leopold Chelsea Boot, $52 (orig. $100) 
• Athlefit Lug-Soled Chelsea Boots, $34–$36 (orig. $66)

Dream Pairs Chelsea Boots, $34 with Prime 

Amazon’s October Prime Day, or Prime Big Deal Days, doesn't officially happen until October 8, but some deals are pouring in early — including one on these Chelsea boots. They have a small heel and a little lift thanks to the thick platform sole, plus a pull tab to help get your fuzzy sock-wearing feet into them. 

One shopper walked “literally tens of thousands of steps over uneven cobblestone streets, up and down hills” in them, while others likened them to similar pairs from more expensive brands, including one seen on screen in Only Murders in the Building.  

Steve Madden Leopold Chelsea Boot

The chestnut pair of these Steven Madden boots might mirror Winslet’s the most, but stock is low. While more muted, this soft beige color might have more opportunity for wear and should show less salt stains. Just pick up a suede protectant, if you plan on wearing them as the weather worsens. 

Athlefit Lug-Soled Chelsea Boots

If you want a heeled boot, this pair will get you off the ground slightly more than the others. But even so, they “give great support like my tennis shoes,” said one shopper. They’re also one of the more highly discounted pairs, so if that’s a swaying factor, these should be one of the first to consider. 

Keep scrolling to shop more Chelsea boots inspired by Kate Winslet now. 

Dr. Martens Embury Leather Chelsea Boot

Mysoft Chelsea Boots, $31 with coupon and Prime

Hawkwell Chunky Chelsea Boot

Vepose Chelsea Boots, $42 with coupon