How To Style Chelsea Boots in Winter Over 40

Boot season is here, and it’s always nice to have a casual pair you can throw on and go—something a little more refined than your cozy UGG-style booties, yet still laid-back and effortless. Enter the Chelsea boot. These lug-sole slip-ons are the perfect alternative for winter: easy to wear, versatile enough for your entire capsule wardrobe, and a simple way to add a bit of edge to your everyday style.

Whether you’re pairing them with jeans or dressing down a skirt or dress, Chelsea boots instantly create an unexpected, on-trend finishing touch.

Here are nine stylish ways to wear them this winter, featuring trending pieces to refresh your wardrobe.

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