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.
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.
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.
Outrageous and Fantastic
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.