I Heart Sadie Smith. I love freckles, use a sheer tinted moisturiser so that they show through, try Juice Beauty SPF30 Tinted Moisturiser. 

I Heart Loretta Young. If you love a gloss but feel it never stays on try MAC Pro Longwear Lipglass in Driven by Love.

I Heart Leelee Sobieski. Go bold with your eyeshadow and try a mossy green, I love the chartreuse shade from NARS Rater R Eyeshadow Duo.

I Heart Lisa Bonet. Whether you have the bone structure or not try using a cream shade a few tones darker then your natural skin tone to define eyes & cheekbones, I love Becca Lowlight Sculpting Perfector.

I Heart Penelope Tree. Drawing on your lower lashes may not be office appropriate but you can still emphasise them to be soft and fluttery, try Kevyn Aucoin The Volume Mascara which has a tiny little brush for precision.