When J. Jill sent me an email asking me if I’d like to sample one of their new chino pant styles, I checked out their website and thought, “Huh. Not exactly ‘me’.” And they’re totally not – they’re way more conservative than the stuff I usually wear – but, you know, I’m open-minded about clothing, so I requested their “boyfriend” style (available on their website starting Feb 1). Surprising me completely, I love them and have barely taken them off since they arrived. They’re more lightweight than you expect, and just baggy enough to be kinda cool while still making me feel a smidgen like Carolyn Bessette.

Above they’re worn with a Theory button-down, but to de-prep the look a bit I’d do a white ribbed tank, heels, and big gold jewelry.