If you’re looking for a style fit for fancier occasions, opt for our luxury pick, Prada’s Chelsea boots. They’re durable for inclement weather, comfortable, and also a classic style. Our top pick for versatility and style is Dr.

Whether you’re looking for a classic or want something a tad more bold and modern, we’ve got your search locked in with our top picks for the best Chelsea boots in a range of sizes and materials. “They were originally produced only in leather with a very limited color palette but can now come in a variety of colors, materials, and textures, depending on trends,” fashion history expert Maureen Lehto Brewster tells Byrdie. Since growing in popularity and becoming a more timeless boot style, Chelsea boots have seen upgrades to their soles and fabrications. On top of that, many Chelsea boots are designed to withstand rainy weather, so you can wear them without worrying about ruining them, slipping in puddles, or accidentally soaking your feet in a surprise rain storm. They’re comfortable and cool plus, they can often moonlight as a dress boot (depending on the construction and fabrication). The defining factors of Chelsea boots are the lug soles, elastic gussets, and pull tabs that allow wearers to slip them on and go, experts say. The style-derived from a men’s boot made popular on the streets of London-features a few key components that set them apart from other boot silhouettes. With their iconic silhouette, Chelsea boots are a mainstay of fall and winter, both for practical and trendy dressers.

Wilde Low Chelsea Boot