Try teaming a multi colored chevron crew-neck sweater with charcoal jeans to pull together a really dapper and city casual outfit. Bump up your look with a pair of brown suede chelsea boots. Can you see how extremely easy it is to look dapper and stay snug when colder weather arrives, all thanks to outfits like this? If you frequently wonder how to dress as a man in his 20s, this ensemble is a perfect example.