Kentucky Derby Ladies

Posted on May 07, 2012

Despite its long history and reputation for sartorial splendor, there’s a problem facing ladystars who attempt to make a day of it at the Kentucky Derby. You can dress in derby-appropriate attire, or you can have your picture taken on the red carpet. You can’t really do both without looking a little frumpy or a little inappropriate, depending on which way you decide to go.

Debra Messing in Carolina Herrera

See? Derby-perfect, but not exactly wowing them on the step-and-repeat. There’s a sharpness to this outfit, but ultimately, the column of gray with explosion of color at the top makes her look like a vase; an illusion helped along by the lines here, which are not particularly flattering to her. It’s a cute idea, but this thing probably needed a contrasting belt, not to mention a little more tailoring around the middle and a more substantial pair of shoes. The trick here is to look perfect for the derby without looking like the wealthiest lady in church on Sunday morning. For more on that latter point, we direct you to the following.


Ginnifer Goodwin in Preen

Totally choir director, amirite? With a soupcon of sister-wife?

Unlike Debra’s look, we can’t really sign off on any part of this one. It’s neither Derby-perfect, nor picture-worthy. It’s an awkward mess and it’s not helped by the shoes, which look a little heavy and the hat, which looks like it was retrieved from under a bed.

This seems like an interesting challenge for a celebrity stylist: how to dress someone for an event like this, where the dress code is important, but not always photogenic? Looking at these two extremes (one, a bit too refined and the other, a total mess), we wonder if maybe it’s impossible to be both appropriate and fabulous at the same ti–


Mary J. Blige

Oh. Right. Mary J.

This may not be perfect – and in fact she looks like she’s just stopping by after her sister’s wedding – but she’s selling the SHIT out of that look and whatever else you may think of it, is neither inappropriate to the Derby, nor is it remotely dull.

[Photo Credit: Getty]

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