The Best Winter Boots Styles Part 2

Chelsea Boots
The Swiss Army knife of your shoe rack. The Chelsea is by far the most versatile shoe you can buy. According to Kacamata Rayban, the right pair goes just as well with a suit or tailored pants from Monday to Friday as with a leather jacket and tattered skinny jeans for a weekend appearance.

Suede Chelsea boots are undoubtedly bad, but it’s a delicate material that’s hard to keep flawless after a downpour. If you don’t need to be cleaned, brushed and treated with protector spray regularly throughout the winter, just choose wipeable leather instead. A pair of smooth black leather comes much closer to the iconic original anyway.

The details to watch out for include autumn rubber soles and the classic heel pull, a practical feature that many modern iterations don’t (but should) have. Also watch your toes. Pointed-toe Chelsea boots look a little different, at least in combination with a suit. Instead, keep an eye on the round shape.

Ankle Boots
In our view, there are only a few cases where wearing Desert or Chukka boots is not a good idea. While their medium-weight construction makes them a clear choice for spring and summer, they are a real killer option for the winter months, along with other ankle-tickling styles such as Jodhpur boots and flat walkers.

Thanks to this intermediate profile, most ankle boots are elegant enough to be combined with a turtleneck, a blazer and chic wool trousers, but also not so fussy that they cannot be combined with chinos and a crew-neck sweatshirt. Perfect for finding your way around the dress codes of the winter months.

Leather pairs are a breeze for cold and wet and offer resilience and lasting elegance. Suede pairs can also be used if you take the time to treat them regularly with a protective spray and always check the forecast before you leave home.

Treat this style – especially chukka or desert boots – as a smarter and more durable alternative to shoes and sneakers. Combine them with chinos, button-down shirts and crew-neck pullovers to create sharp, warm outfits that pass the pub safe test with ease.