Navy and khaki is about as close to a sure thing as menswear gets, and this pairing doesn't mess with a good formula. The Everywear shirt's shorter, modern length and stretch fabric mean it layers clean or stands alone, moving like a knit while looking like a proper button-down. The slim tech pant keeps the silhouette tailored, and the stretch and water resistance mean the commute in doesn't leave a mark on the meeting.

Finish with brown leather derbies and a woven belt.