Gold Cup quandry solved. Sort of.

"I am going to Gold Cup and I have a fab Kay Unger sundress to wear and I want to wear a pair of brown/nude/beige heels. I prefer 3 inches and higher. My only problem is that I will be standing around outside in the grass and I don't have to spend the entire time leaning on my toes while trying not to fall over after too many bourbons. I have a pair of wedge sandals that I bought last summer but I just feel like the dress calls for something more delicate than wedges. Suggestions?"

I won't sugarcoat it -- this is a no-win situation. Either you go stiletto and put forth some effort, or you go chunky and look like, well, the kind of girl who'd wear a chunky heel.

As my own skinny 4-inchers sank into the soil this morning when I scampered across wood chips, flowerbeds and condom wrappers to collect that which the preciousness at right "left behind" (click for full precious effect), I was reminded even before I received your e-mail just how impractical a high heel can be when treading on less than solid terrain.

That being said, in this and in every situation, I will always advise you as I would advise myself: set practicality aside and do what you have to do to look your best. If that means putting more weight on the balls of your feet for hours on end to avoid turning your stilettos into golf-tees, then so be it. Stay on hard surfaces as often as you can and instead of complaining when the pain becomes too much to bear, make like a socialite and toss out an airy, "Oh goodness, the crazy things we do for fashion!" to those women with their overweening smirks who, despite their dearth of male suitors and jealous up-and-down female glances, are still under the impression their sturdy square-toes were the proper choice. And finally, when you're on the verge of kicking those heels off, try to remember and revel in the fantastic posture those 3+ inch heels afford you.

I know many of you will disagree with me on the just-deal-with-the-pain front, but in my opinion, the reward of feeling like the best-dressed minx in the crowd is worth all the pain and effort I've just described.

It is the Gold Cup, after all.

Even though I don't have the specifics on your Kay Unger dress (love her designs, by the way), I do have the most important information, which is that you already know you want a nude, fairly delicate, sundress-complementing pump or sandal. You didn't mention a the specific price-point you were looking for, but assuming you and I are in similar financial situations, I took the liberty of only looking for pairs under $200.

My recommendations:
1. Esen by Miss Sixty ($173.95 at zappos.com)
2. Tammy by Tahari ($105 at piperlime.com)*
3. Gabay by Anne Klein ($75 at piperlime.com)
4. Maylie pump by Enzo Angiolini ($56 at lorisdesignershoes.com)
5. 3468 by Vic Matie ($188 at lorisdesignershoes.com)
6. Chance encounter pump by Seychelles ($79.95 at endless.com)
7. Faith sandal by Martinez Valero ($128.95 at nordstrom.com)
8. Drama slingback by Via Spiga ($189 at nordstrom.com)
9. Carina open pump by Nina ($89.95 at ninashoes.com)
10. Palermo by Dolce Vita ($132 at pinkmascara.com)**

*your editrix's top pick (shown below)
**your editrix's second pick (if your dress is a neutral shade)