White-Soled Penny
$575 by Canali.

Plain-Toe Driving
$475 by Tod's.

Burnished Bit
$590 by Gucci.

Contrast Leather Tassel
$248 by Coach Men's.

Oxblood Penny
$1,050 by Brunello Cucinelli.

Loafers, $650 by Ermenegildo Zegna. Left: Chinos by Shades of Grey by Micah Cohen. Right: Suit pants by Gucci. Socks by Pantherella