In Defense of Four-Furlong Hats

This past weekend, I traveled to the delightfully quaint and lively city of Saratoga Springs. If you've never been, I highly recommend it. Long, shady streets lined with Victorian summer rental houses, endless lawn parties, a preserved 19th-century racetrack, a lake, hot springs, and a row of beautiful shops. Even a great boutique called the Pink Paddock, for all us Lilly fans!

I spent only one night in Saratoga, and my big brother and I had a great time betting on horses, enjoying the weather and doing a nice bar crawl. But my favorite part of visiting Saratoga, primarily the track, is the people-watching, which is better than you'd expect. While the crowd is classier overall than, say, Belmont, the attire still runs the gamut from shots-and-T-shirt to bow ties, sports coats, dresses, and, naturally, big hats.

The Kentucky Derby is not only the most prestigious horse race in the country, but the place to wear your brightest, loudest sundress and most immense, wide-brimmed, view-obstructing hat. While I haven't been to the Derby, though I plan to go soon, I may be attending the Travers in Saratoga Labor Day Weekend. And of all races to attend after the Derby, this will be the perfect place to trot around in the most old-fashioned, ridiculous, never-wear-it-again accessory I will ever wear.

Below are some of my favorite looks: ladies in hats, great dress/hat combinations and articles I'd consider buying for the Travers. Others are looks that are just fabulous for how ostentatious and quintessentially southern they are. I won't make this a huge investment piece, for obvious reasons, but the thing to remember about bonnets is this: the bigger the hat, the more you need to spend to keep it classy.

Enjoy!

Classic & Beautiful

Wide floppy brim, and appropriate ornamentation (the Run of the Roses!)

Hef and his girls, surprisingly classy. My favorite is the one on the left - simple (skin-tight!) solid dress with a straw hat, with added ribbon and dark glasses.

A more fashion-forward choice, in a neutral color. I love the asymmetrical brim.

Lilly's take on the Derby. Great straw hat with her signature print ribbon, and you could probably pull off wearing it to the beach (the right beach, of course).

On this champagne-colored bonnet, the featheres and ribbon don't look too-too because of the neutral, uniform color family. Plus, the more structured brim keeps the hat out of your face, not obstructing the line from the mint julep to your mouth!

Runway Derby look.

Black and white all over - clean, timeless and the most formal combination.

Outrageous and Fantastic

I hope the people sitting behind her got discounts on their tickets. But those feathers are simply wonderful!

Good effort pairing this textured periwinkle hat with a white dress, but the flipped-up brim and cutout pattern are just not quite right.

Audrey Hepburn. The only woman who could pull off a hat that weighs more than she did.

Found on a couture hat website. Might work with a solid black dress, but the heat defeats that, and the big white rose is a bit matronly. Still, not the wackiest one I've seen.

Now this. Is what a race hat looks like. Bright colors, piled-on flowers, wild feathers, netting and a huge brim.

Another black-and-white confection, which isn't bad in theory, but the porous material would give me a headache when the sun came through. Besides, why go this small-and-tall when you could go big-and-broad?

One word: titanic.