The Kentucky Derby, sometimes called the “Greatest 2 minutes in sports” is all about spectacle. And let's be honest, the horses are only a small fraction of the Derby's appeal. When I think of the Kentucky Derby I think of three things: mint juleps, pastel, and hats. Big hats, colorful hats, hats bursting with feathers and flowers; generally it's the ladies that get to be the headwear show ponies (Horse jokes! Don't hate.) but let's not forget that the Derby is where menswear gets to be playful. Brightly colored suits, pastel prints, preppy bowties, the styles aim towards taking the usual formality of suit and tie and turning it into a springtime celebration. The key is to have fun but maintain a tasteful elegance throughout, and with some of the custom brightly colored Borsalinos and Phrenology hats Porkpie Hatters has been making, it's becoming easier to bring this style outside of the tracks.
But wait, you may say, that may do well for Kentucky, but seersucker in the city? Yes seersucker in the city! Yes to an impeccable cream panama. Here's the biggest key to making a Kentucky Derby, southernly smooth, dandy gentleman look relevant to the gritty streets of NYC: Have fun with it. Not comfortable with wearing a full pastel suit? Pick elements that will pop like matching your necktie to a brightly colored hatband on your straw boater. Want to add a little edge to your look? Add some graffiti style prints to your repertoire. It's not for everyone but designer Walter van Beirondonck's Fall 2012 collection is one of my absolute favorites for turning formal menswear on its head. Though the runway looks themselves definitely skirt the edge of weird, there are positive elements to take away from the collection. Take note of the bright color combinations and the mixture of old-school prints with graphic details. It's about playing, taking details that we consider very prim and outmoded and literally cutting new shapes into them. The cuts are well tailored and slim. The print combinations and color choices are eye-catching and complimentary. It's not just being weird for weird's sake, it's holding up a mirror to what we attribute to formal wear. Although this collection was meant for a more in your face audience and colder weather (a leather bowler might be a bit much in the sun for both stylistic and practical reasons) the color choices, combination of prints, and colorful headwear to match are definite style notes to incorporate into a reasonable wardrobe.
The Kentucky Derby happens only once a year, but if we're breaking the seal on that light grey suit, I say keep it in play. Keep pairing the classics with unexpected twists, and you've got a look that is continually fresh and relevant. I'm actually going to quote the Kentucky Derby's official website where they opine on what's the usual attire for their event: “...Men just need to be confident. No matter what you wear, it's how you wear it, gentlemen.” I think that is great advice. Feel confident. Have fun. Go on, tip that brim to a jauntier angle, it's spring!
For those that feel they need a little more inspiration, I threw together a quick pinterest board, including actual looks from street snaps and such. The industry can oft bend towards fashion for fashion's sake so it's refreshing to see looks pulled off in the wild. Check it out here.
Using a tape measure, measure the widest part of your head (just above the ears and eyebrows) to the nearest 1/8th of an inch.
If you have not purchased a new hat recently, please remeasure your head, as sizes may change depending on hair style, weight loss/gain, and age.
If you are in between hat sizes, try this cotton sizing to make adjustments at home.
For more information on stretching a hat, click here
How do I measure my glove size?
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