Oxford Shirt
To avoid looking like Tom Cruise in Risky Business, ditch the boxer/high socks combo and wear your guys work button down with a simple high-waist belt, basic leggings, and these pretty-in-pink Sam Edelman flats. We're also obsessed with this Fall 2014 Marc by Marc Jacobs bag - it ties the look together and it's practical.
Uniqlo Men Oxford Slim Fit Long Sleeve Shirt, $29.90
Marc by Marc Jacobs 'Sheltered Island Jamie' Satchel, $578
Sam Edelman Ballet Flats, $115.15
LNA Olivia Cotton Basic Leggings, $53
Maison Martin Margiela High Waisted Leather Belt, $295