a kentucky gentleman dresses for the derby


The fabled Kentucky Derby is arguably the most important event for which a Gentleman dresses each year. As the Kentucky Gentleman is foremost among God’s chosen children, the Derby is not only the pinnacle of equine competition: it represents the purest expression of sartorial prowess possible. As in all things, the Kentucky Gentleman must be exceptionally deliberate and meticulously thoughtful when selecting his garb in early May. As such lofty aspirations cannot possibly be condensed to a single volume, visit again tomorrow for the conclusion.

Great buildings require firm foundations – the perfect Derby assemblage is no different. Begin your look with a crisp, well-tailored white or muted shirt. The cut is a matter of personal preference – this should reflect the Gentleman’s build. There are, however, several key details that should be considered.


Material is crucially important, but must to some degree be chosen with a nod to Mother Nature – choose a breathable material that holds its shape well. A weightier shirt will hold that crisp appearance race after race, but is also likely to result in unsightly sweating if early May brings warm, humid air. Linen is wonderfully breathable, but the Gentleman who dons it should be mindful of its tendency to wrinkle. A lighter cotton shirt is a fine choice, and should serve the Gentleman well through the day’s events.

While the cut is up to the wearer, he must be conscious of the collar and cuff. Far too many men wear collars that are too tight – you should be able to fit your forefinger between your collar and neck. When purchasing a shirt, ensure that the collar is properly sized, as this is the most difficult feature to alter. A skilled tailor can cut the rest to fit. Where collar style is concerned, remember that the Derby is a special occasion – a button-down collar simply doesn’t offer the formal appearance of a spread or forward-point. To achieve the exacting look he demands, the Kentucky Gentleman will wear a lesser-known tab collar, which provides the aesthetics of a forward-point with the function of a button-down. Ensure that your collar (indeed, your entire shirt) is well ironed and properly staid.

The Derby is a wonderful opportunity for the Kentucky Gentleman to add some splashes of color to his look – even if his more common trappings are decidedly neutral, the saturated selection undoubtedly donned by his companion will justify any and all lively colors he should select. Embracing once again the uniqueness and historic nature of the day, the Kentucky Gentleman will select a colorful bow tie, preferring to root plant himself confidently in timeless tradition. This is, after all, a look he dons for pure pleasure. Consider the following beautiful offerings from Vineyard Vines’ Derby Collection.

Sleeves and their attendant cuffs are, in this Gentleman’s opinion, an opportunity far too often missed. A Kentucky Gentleman never misses such an opportunity. The Derby outfit is won or lost on the details, and the sleeve provides a wonderful canvas. As a jacket of some sort is always part of the Gentleman’s wardrobe, an effective sleeve must be of appropriate length – short sleeves and jackets should not be paired in this case (if ever). The cuff itself provides a further opportunity for expressive detailing, as the Kentucky Gentleman has at his disposal a wide assortment of cufflinks. A french cuff provides both visual interest and increased function (the cumulative weight of cuff and link will ensure that cuffs are not lost in jacket sleeves), and is an essential element of a well-rounded wardrobe.

Cufflinks and Kentucky both representing personal passions, this Kentucky Gentleman prefers Derby cufflinks that pay homage to the Bluegrass State, such as the official cufflink of the Honorable Order of Kentucky Colonels pictured below. Have fun with this… cufflinks are the perfect place to add your own piece of flair.

Andrew, a Kentucky Gentleman

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