Chelsea boots are like a fine (high proof) cognac — the taste is acquired and easy to over-do it your first time around. Just as many gents started rocking suits again in the menswear boom, this iconic style has seen a resurgence amongst discerning individuals who won’t settle for the standard dress shoe. Unless you’re cool with the whole sophisticated cowboy look (seriously no harm in that), the Chelsea is by far the best boot to wear with a suit.
This is a completely different game than the rugged leather boots we champion here at Selectism. It’s a tough jump to just start wearing Chelsea’s everyday — a slow and studied approach always wins. Do what feels natural. We’ve rounded up our 10 favorites of the season that need your consideration. See above.
See our other Buyer’s Guides here.