Shoes?

I figure the best way to do this is to begin with what I have and what works for me, and go from there.

The inner circle are the shoes I wear more often, and the outer circle are my "specialty" shoes.

Starting with the Maroon Converses:

• Maroon Low-Top Converses with Inserts
  
• Black leather Franco Sarto pumps, with arch support sticky things inside
• Black Low-Top Converses, same 20z miracle inserts as the Maroon
• Moroccan Babouches - not a lot of padding for the foot, but still fun as hell to wear
• Sofft Wedges - bought on sale at DSW and fantastic heels that don't kill my feet much
• Gold Ballet flats from Payless, with a Dr. Scholl's Arch Support insole; my favorite work shoes
• Born sandals - unstylish but comfy as hell and the BEST travel shoes

Outer Circle:

• Red Aldo Moccasins - rarely worn because the leather insole is falling out
• Black Oxford pumps from payless - not terribly comfy but cute & good for wet or cold weather
• Ivory Hot Cakes heels - cute, comfy, and I own a pair in white. the heel is too low and they look too casual for a wedding
• Black strappy "The Touch of NINA" shoes I bought for formal night on the 2007 cruise; they don't kill my feet, per se
• Payless' American Eagle brand chocolate T-straps. If these came in black, I would never need another pair of shoes, ever.
• Black T-strap Oxford style heels by Nine West. Great, but not as comfy as the aforementioned shoes
• Jewel tone gladiator sandals from Plato's Closet, cute as hell but awful to wear all day
• Strappy champagne Daisy Fuentes heels that I bought for prom. I only wore them for three hours or so, and I don't remember them as being terrible. Probably backup shoes in case I can't find good bridals
• Black Old Navy flip flops - necessary, cheap, and comfy
• Brown faux-suede pumps with floral detail from Payless' Highlights brand, bought for Senior year homecoming
• Black slouchy faux-suede boots from Payless, bought to wear to the Renaissance fair, require inserts as well.

So, a breakdown of what works for me:

1. Insoles - I buy them and I use them everyday. My arches are high, my heel bones perpeutally hurt, and if I don't wear them then my knees hurt too. I'm also prone to blisters.
2. Payless - I've bought tons of shoes there over the years, although I am trying to do more DSW, but the prices can't be beat!
3. I like to buy cute shoes - but I wear my unstylish, comfy ones more

So what are my options for cute shoes with heels, that I can strut down the aisle and then rock out all night in without wanting to cry from my heel/arch pain?

Options are forthcoming in post #2