Ana, you are a tough cookie to challenge. You have an innate style that I envy. You have scored perfect 10s on some many different looks. (I don't think I had a chance to post on your recent outfit with the cargo clams. I adore that look.) In particular, though, you have perfected the feminine polish the evokes the late50s/early 60s, a la "mad men."

My challenge to you is to choose another era to evoke. It could be something romantic like the 20s flapper or boho like the 70s hippy. Maybe you bring out your 80s flair with those Ray Bans. Of course, the key is to not look costumed but to reference the look in an updated way. We'd love to see some style inspiration through pictures in your post, too.

Have fun! I can't wait to see what you come up with.