When matched with tailoring, boots show you mean business and know what you’re doing. They give the wearer a boss-like appeal that other shoes can’t mimic, transforming a regular suit into a … See more

• Trouser length
• Arguably the most important thing to consider when pairing bootswith a suit is the three-inch area around where your trousers end and your bo… See more

The Chelsea has long been the go-to boot style for pairing with a suit. With its sleek, sculpted silhouette and high, narrow ankle, it slips seamlessly under a pair of trousers without ruining their line. While they were born into regality – Queen Victoria was said to have originally commission the style for riding on horseback – they … See more

Chukka boots are arguably the ultimate in-between shoes; not too smart, not too casual. This makes them a natural pairing for jeansor chinos, but they can also work well with a suit. A Far Cry from Chelsea boots, the chukka isn’t the dressiest silhouette – with their flexible crepe soles and soft yet durable suede uppers – so they instantly add a l... See more