Shoe: I Basic Sandal (Zara, $50)

From the Left, Earrings: Oscar de la Renta Earring ($185) Bag: Rebecca Minkoff Black Studded Clutch ($195) Ring: Ruby Kats Dolce Vita Ring ($155) Dress: Tsumori Chisato Bi-Color Dress ($357)

From the Right, Bracelet: Gold Hinge Clutch ($41) Bracelet: Satin Gold Clutch ($60) Clutch: Portfolio Clutch ($36) Sweater: Zero + Maria Cornejo Ruched Turtleneck ($248) Jeans: Moto Skinny Jean ($76)

For a Gallery Opening. I appreciate the deconstructed look of this dress, even though I’m not sure whether I would be bold enough to wear it. (If you want something more structured in the same color palette and a lower price point, click here.)  But the bold style is the perfect compliment to the sassy, colorblock shoe.

For the accessories, I wanted to choose pieces that were interesting but not overpowering.  The earrings are a cool geometric shape, and who can resist Oscar?  The bag is a rocker studded clutch, this was a substitute because I really wanted a large foldover clutch.  And the ring is hammered metal with enamel, you could also add more rings if you were feel like making a statement.

For the hair, I’d recommend stick straight with a center part.  You could also do a high, tight updo with pomade for smoothness.  For the makeup, a red lip and strong eyeliner.  I’d also paint my toes a traditional red.

For a Casual Dinner.  When I wear bold shoes, I like to go easy on everything else.  Here, I paired a simple skinny jean in black with a slouchy turtleneck sweater.  You could also reverse the proportions and do a snug-fitting turtleneck on top and flare leg or boot cut trousers on the bottom.

The accessories are fairly straight forward.  I paired a couple of bracelets with simple clutch (the purse matches the shoes!).  I’d probably wear the bracelets over the cuff for full effect.

For the hair, I would wear it up in either a sleek ponytail or a low bun.  For the makeup, neutral colors on the eyes, a blush cheek and a soft rose lip.  For the toenail polish, I would choose either gold or orange.