If I'm going to splurge on a pair of Louboutins...

Louboutins will always be in no matter what the style, they are timeless and classic. I would go for any of the shoes that you posted, personally I really like the green patent mary janes. I do hope you invest in a pair!
 
I like the Simple style in the first pic - I am biased. I just got a pair with an extra 15% off from Bluefly and love it! I am usually a US6.5 or 7 and the website listed the shoes as US7 but they are European 37.5. The shoes fit nicely and the heels aren't too high. The shoes will last forever as the style is so timeless. Oh btw, it's quite sexy to have the 'toe cleavage' showing with this style ;)
 
Ack! I was all ready to order the camel pointy toed d'orsays from Saks, but I'm not sure if there is a free shipping promotion going on. Does anyone know? :nuts:

Travel Bug - Thanks for the sizing info. I went ahead and chose a 40.5 for the size, since sizing up seems to be the consensus. The CL espadrilles I have are a 40, so sizing up will probably work.