a kentucky gentleman dresses for the derby- part 2

A Kentucky gentleman always keeps his promises – thus, here is the second installment of our Kentucky Gentleman’s Derby advice, fresh from the paddock! Segment one covered the foundation – the perfect shirt. Now, it’s time to cover some of the finer points of the derby outfit.

A well-planned Derby outfit (and, in point of fact, any outfit) should always include pants – unless your tickets say ‘infield’ on them, in which case this may not be the post for you! Look for a mid-weight chino in a light color, which will handle the glaring sunlight far better than a darker pant. As with shirts, the lighter, more breathable fabrics will risk wrinkling, while the heavier weaves are insufferable on warmer days.

Make sure that your pant fits correctly – again, buy for the most fitted part, in this case the waist, and tailor the legs to fit. Pleats are a matter of taste, but there is simply no excuse for pleated trousers with a ballooning effect or flat-fronts that pull at the pockets. Cuffs, as with shirts, are at the discretion of the wearer, but serve as a weight, encouraging a straight line and clean break at the shoe. Shoes (being an accessory) are another place that the competent Kentucky Gentleman will choose to express himself. A more traditional (albeit formal) shoe might suffice, but will stop short of the prowess the Kentucky Gentleman always displays. A saddle, oxford or spectator in a two-tone finish will anchor his appearance and draw the eye down, ensuring that his look is fully appreciated.

While runway models and Kentucky Derby celebrities have, in recent days, brought welcome attention to the Run for the Roses, the balanced Kentucky Gentleman understands that – in this case – tradition wins the day. Kentucky is rife with it, and her native sons will not have spent their morning in a salon chair, prepping for the red carpet. Thus, the Kentucky Gentleman will shy away from the more fleeting trends – embroidered pants, lime green corduroy, etc. – in favor of what they know to be true: some things simply do not go out of style. A classic look, properly accessorized, is a testament to both race and spectator.

Tradition being a predictable mistress, it is assumed that the discerning Gentleman will tie his look together with a sports jacket. The addition of a second layer permits some control over temperature, as the jacket can easily be removed if the occasion requires extended time in direct sunlight. The cut once again falls under the domain of preference, but must be well-tailored. Look for a two-button affair, as the lines it creates will draw the eye in, creating a slimming appearance. As this is an equestrian event (and the Kentucky Gentleman is, of course, an equestrian), details that evoke the heritage of the sports-coat – which, oddly enough, came out of equestrian sporting to begin with – will be greatly favored. Hatch pockets and patched sleeves create an aura that will have fellow spectators valuing your selection in the eleventh race above all others.

Jackets also provide an opportunity for personality by the addition of a pocket square. The Kentucky Gentleman will select a pocket square that accents both his and his companion’s looks – a bright color will provide another pop of visual interest to keep the eye moving. Look to this guide by Brooks Brothers for advice on folding this most Genteel handkerchief. Once again, Vineyard Vines’ Derby Collection offers an excellent option.

This brings the Kentucky Gentleman to the last of his Derby accoutrements – the hat. Hats are a lost and forgotten art, but the Derby provides an excuse to return to the polish and flair of yore – and, as previously stated, the Kentucky Gentleman does not miss opportunities. Unlike that of his companion, his hat selection is born of participation, not of competition. Straws and felts are excellent choices, but in the former be careful to select a lightweight fabric, as heat becomes an issue rather quickly. In straws especially, the addition of banding is another place to add a colorful twist.

Andrew, the Kentucky Gentleman

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