The Cigar Shirt
Photo/Jeff Harris

Baron Enrico di Portanova (Ricky to friends) was a man of outsized appetites, a multimillionaire jet-setter who considered sun, sex and spaghetti the best things in life. The heir to a Texas oil fortune, he owned a string of palatial homes, entertained a who's who list of the rich and famous and thought of his Lear Jet as a taxi. But the image for which custom clothier Harris Reiss remembers him best is a 1981 photo taken in Monte Carlo showing Baron Ricky smoking a cigar while styling an ascot under an over-shirt. Custom made by a tailor in Rome, it housed six cigars in slots across the breast. Reiss, who had an earlier career in cigar retail, first saw the picture in his youth. He retained the memory long enough to find the perfect cotton twill and engage the right artisan to recreate the look. Now Reiss offers it by custom order in five colors (including tobacco). It comes with room for accoutrements in the large waist pockets and the option to order the cigar slots to fit your favorite sizes.

Cigar aficionados have long sought clothing to accommodate their pursuit—not only with the traditional smoking jacket meant to absorb smoke, but through design features added as cargo space. While Ricky chose to wear his enthusiasm on his chest, smokers with a more reserved bent could always find a Savile Row tailor willing to hide special pockets for cigars, tools and even weapons within the confines of a business suit. The Baron's shirt was clearly a riff on a safari jacket, with overlong versions of the slots in which a hunter would normally keep his shotgun shells. Reiss's version ($350) can be worn with or without a shirt underneath, comes in short sleeves as well as long and offers different collar and cuff treatments.

Another time-honored, cigar-wear option is the classic guayabera. Its main bona fide as smoking garb is that it has huge cargo pockets (typically across the front) and—oh yeah—comes from Cuba. As such, it is an unsurprisingly lightweight and casually fitted shirt. An identifying feature is the typically fanciful fabric detailing. As most come in short sleeves they don't qualify as the over-shirt that Baron Ricky wore, however.

While Reiss's cigar shirt is made by a New Jersey tailor, he offers it to customers across the country, with delivery in four to six weeks (call for details). This will not be Reiss's last foray into cigar raiment. He is at work on a recreation of the piping-trimmed smoking jacket that the overly self-confident Hollywood producer Jack Woltz sports in the first Godfather flick. Happily, it won't come with a horse's head.