The Chelsea boot is the shoe equivalent of that blazer we keep mentioning in that it works across more situations than almost anything else in your wardrobe and deserves a place in pretty much every man’s rotation regardless of what else he typically wears. The elastic sided silhouette is clean and minimal and that minimalism is exactly what makes it so adaptable. It works under suit trousers in a way that feels contemporary rather than overly formal. It works with straight jeans in a way that looks deliberate. It works with more casual outfits in a way that adds a bit of sharpness without overdressing the look. Black Chelsea boots in a smooth leather are as close to a universal answer as footwear gets. A tan or brown version gives you something warmer and more casual that works brilliantly for weekends and smart casual situations throughout the year.