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#92 - Equestrian

#92 – Equestrian

Equestrian
Price: Saddle sores/horsemeat scandals

If you are serious about being wealthy, one of life’s great pleasures is developing a sense of class that is far beyond that of the common man. This means enjoying activities like polo, croquet and collecting ascots. While nearly everyone has donned a cowboy hat and straddled a petting zoo pony or mounted a dude ranch work horse better named Gluestick than Silver, the truly wealthy do not consider these representative of a true equine aficionado. In fact, the rich consider anyone that wears blue jeans and a straw hat more likely to be proficient with a pitchfork and a wheelbarrow than a saddle and a bridle. Instead, one simply must own a proper collection of riding boots, flared riding pants and a helmet reminiscent of Marvin the Martian, if Marvin owned a Bentley.

While a trusted steed may elicit images of John Wayne, the Lone Ranger or Clint Eastwood, rich people know that only and elite few can exhibit the grace and elegance of an equestrian rider. The majesty of rider taming a well-papered beast and becoming one as they gracefully vault over obstacles in a race against time is akin to watching a an Italian mechanic tune a classic Ferrari…while it is moving. Equestrian may at first blush appear a frivolous pastime but one must move beyond the literal interpretation and realize it is in fact a metaphor for success as many wealthy patrons believe they have pulled themselves up by the bootstraps overcoming humble beginnings as trust fund children who did not see a penny until they turned 21 or until they narrowly graduated from an Ivy League college at a campus littered with buildings named after their forefathers.

As always, the challenge is not how to mock the frivolities of the wealthy but to embrace them as a means to gallop into the inner circle. Naturally, as with other stuff rich people love, there is a vocabulary to learn. Understanding that the obstacles are called verticals or fences and that the horse and rider are called jumpers is table stakes, so the ability to discuss the finer points of the sport becomes critical. I recommend intimating a knowledge of dressage or perhaps the cultural importance of the fox hunt as light-hearted means to inspire your host to wax poetic on their thoughts about warmblood and thoroughbred breeding or their leaning towards Badminton versus Burghley as the pinnacle of success. Some may suggest that sincerity and genuine interest are keys to winning friends and gaining influence. Others believe that rich people are much more inclined to appreciate a sycophant that feigns interest rather than engaging in meaningful dialogue. Perhaps it is why horses make such great team mates.

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#91 - Fine Wine

#91 - Fine Wine

Fine Wine
Price: French Lessons

One of life’s great joys when you are “comfortable” is being able to distinguish upon which side of the hill grapes were grown, weather patterns that summer and on which day they were picked by delicately inhaling. Bonus points to those who can name a delightful boulangerie, a five-star hotel and a helipad within a five mile radius of the vineyard. Few topics can enthrall the wealthy the way that debating the finer points of a vintage Chateau Lafite can but be warned, there’s hardly any point to speaking about a bottle corked more recently than the Reagan administration.

Taking a stroll through your local gas bar could lead you to believe that all good wines come in a box or have catchy names like Night Raider, Fat Bastard or Naked Grape. You would be mistaken. Take a gander through the cellar of a connoisseur and you will discover that wines have unpronounceable names from places you’ve never traveled. This is all part of the charm of a great wine, the more obscure it is the more valuable it becomes to the truly rich. Wine is a game of one-upmanship where exclusivity and rarity are as important as an iron-clad prenup and a divorce lawyer with blood-drenched fangs. Naturally, one never admits to buying a bottle but refers to the cases secured at their favorite auction house.

Of course, the challenge as always, is to use your cursory knowledge as the bridge to gaining acceptance by the upper crust. While you would think that fitting in with a group of people that drink all evening would be a simple task, recall that like a first wife, one always spits and never swallows at a tasting so you will not be able to use inebriated-induced charm to win over your tannin swilling compatriots. As gaining superior vineyard knowledge requires time, money, patience and the equivalent of a PhD in meteorology, one must turn to collecting and innuendo to make nice. My best advice is to speak as though drinking your wine is beneath you and you are sure to turn heads. Remain vague and imply that it is crass to discuss the contents of your cellar. Furthermore, refer to cellars that you keep in various countries. Seek to illuminate your flock of oenophiles by imparting upon them the famous words of Lawrence Jamieson, that you collect wine to ensure it is properly cared for but that it is too valuable to drink and too dear to sell. While deep knowledge of tasting notes is impressive, your mystery and aloofness could make you the most sought after vintage in the manor.

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#90 - Sailing

#90 - Sailing

Sailing
Price: Chapped Lips & Wind Blown Hair

If you think a sloop is a rapper, feel ketch is played with a baseball and glove and believe that yawl is a greeting in the southern American states you are likely not rubbing shoulders with the Rockefellers. If however, you are unfamiliar with rap music, believe that ballpark franks are uncivilized and refuse to associate with Confederate sympathizers, you already know that standing topside in Chesapeake Bay is the perfect summer pastime. If you lean more to the latter than the former you are aware that sailing is among the stuff that rich people love

While port, starboard, stern and bow make the average person’s head spin, these are among the first words out of a trust fund baby’s mouth once the proverbial silver spoon is removed. Rich people that do not learn to sail are as out of place as an Amish couple at a swinger’s party or a West Virginian at a wedding where the bride and groom are not related, it’s awkward for everybody. That said these social anomalies are few and far between. Just as every working class American should have a chicken in every pot and a car in every garage, the rich will continue to have a blue water cruiser in every bay and a mooring ball in every harbor. More important, to the rich, than actually sailing their luxury yacht is ensuring that they have the most conspicuous slip at the marina. There is hardly any point in commissioning an 89 foot Oyster yacht if nobody knows it is yours. While size is important, sailing ships are one of the few places that a sense of humor is acceptable in wealthy circles. Witty monikers like Alimony, TARP, and Golden Parachute all convey a playfulness that only money can buy.

The question, as always, is how can sailing help you to befriend the fabulously wealthy without becoming their indentured servant dishing up caviar on the high seas while the aforementioned Alimony is heeling in 45 knot winds. While anyone with a PhD in English literature can land a crew job on a yacht off St. Maarten, it takes a special type of sycophant to ingratiate themselves and secure an aft berth on a month long cruise of the Mediterranean.  To start, learn a few key words like regatta, Maxi class and Top-Sider boat shoes. Next, learn how to tie a bowline, a cleat hitch and a reef knot and know when to use them. Finally, purchase a vintage copy of Slocum’s Sailing Alone Around The World. To bring it all together, plant yourself at the most Jimmy Buffettesque pub in the port reading this month’s copy of Yacht World circling classifieds larger than 45 feet. In no time, you’ll be talking about ports of call in the BVIs with an overweight boat owner wearing the latest Tommy Bahama linen pants and Helly Hansen waterproofs. Word of advice there’s no such thing as a starport jigpole!

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#89 - Cufflinks

#89 - Cufflinks

Cufflinks
Price: Accepting the French

In the immortal words of Little Orphan Annie, “you are never fully dressed without a smile”. This whimsical idea may apply to the vast majority of pencil pushing middle managers trying to keep their head above water in spite of a partner that believes shopping at the newly opened Crate & Barrel is akin to the second coming of Jesus. This little cliché certainly does not apply to the proverbial upper crust. While custom tailored shirts are a staple of any well-to-do wardrobe, they hardly provide the opportunity to flex one’s personality and showcase their avant-garde sense of fashion. Enter the French cuff and Louis XIV’s fashion forward gift to the world, gilded studs called cufflinks.

To the everyday man and woman who feel that Starbucks charging $1.50 for a cup of Joe is unconstitutional the idea of spending hundreds, if not thousands of dollars, on two chunks of semi-precious metal in place of a twelve cent button must seem certifiably ridiculous. It is this difference in the classes that keeps Pabst and Camaros popular in trailer parks and cufflinks in vogue on the Upper East Side of New York. Naturally, throwing on any old piece of kitschy jewelry won’t cut it at the club. While your groomsmen, who believe white socks and tuxedos go together like fried peanut butter and banana sandwiches, will commend you on your compass with built-in thermometer or roulette table cufflinks, you have a better chance of catching Dora the Explorer in Playboy than seeing Gordon Gekko adopting your mischievous sense of fashion or glimpsing Bruce Wayne sporting batman logo cufflinks. Instead, rich people opt for subtle designs that reflect their personal interests. This may be collecting impressionist art, classic cars or a layman’s interest in Adam Smith’s Wealth of Nations and its influence on the credit default swap crisis of 2008.

If you don’t feel a burning desire to retire your dress shirts and adopt French cuffs throughout your wardrobe, fear not! There are two things to remember when befriending the wealthy; as any first year associate on Wall Street quickly learns rich people don’t like when common folk wear cufflinks and complimenting a rich person’s sense of fashion is substantially less expense than dressing like them. While wearing cufflinks will not ingratiate you, asking leading questions will. The trick to making friends with the rich is to walk the fine line between ass kissing and cerebral flattery. For example, telling a wealthy man or woman that their cufflinks are really impressive is blatant brown nosing. Asking if their sense of fashion enhances their success or if their success enhances their stylish appearance is the fast track to gaining the respect of the rich. So next time you button-up before work, think about those inconspicuous pieces of cuff candy and consider how they could enhance your own life.

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#86 - Suspenders

#86 – Suspenders

Suspenders
Price: Chafed Nipples

There are two types of people in the world, those that wear suspenders and those that do not. In the former group there are two types of people, rich men and everyone else. While everyone else is quite broad it includes notable and questionably valuable members of society like clowns, satirical television characters and pseudo tycoons that hope the powers that be mistake them as well bred. This group also includes adorable old men but they are exempt from public scrutiny, a benefit of respecting one’s elders. The considerably smaller group of men that rely on clips to hold their trousers in place do so for one important reason; linking thumbs through these elasticized accessories conveys a sense of unquestionable wisdom, a direct yet subconscious connection to President Roosevelt, thereby solidifying one’s alpha dominance in a room full of everyone else.

If you are like 95% of men, suspenders aren’t your cup of tea and you think that they represent arrogant money grubbers that care more about their Rolls Royce than their personal chef’s welfare. If you are in the 5% of arrogant money grubbers that wear suspenders, you could care less what the 95% think, hope that they stay the hell away from your Rolls Royce, wonder what your chef is preparing for dinner and believe that Michael Douglas was a “real pussy” in the film Wall Street. There are of course exceptions to the stereotypical hard-nosed businessman in suspenders; there are hard-nosed news anchors that make their interviewee weep, hard-nosed MI6 double-O agents that are licensed to kill, there is even a band named Satan Wears Suspenders and of course your grandfather who remains adorable in his suspenders.

The burning question is how can suspenders help you? As mentioned, unless you are in the 5% and a notably wealthy individual you will fall into the category of pseudo tycoon desperately trying to fit in also known as the brown-nosing pain in the ass. Adopting this transparent ruse will likely have a negative impact on your career, destroy your personal life and most importantly eliminate what is left of your sex life as the former crumble. Instead there are three things you can do to elevate yourself in the presence of the suspenderati. First, never snap the suspenders that your boss wears, that their boss wears or those worn by important clients that visit the office. This will inevitably lead to a stint counting ball bearings in a city that Detroit natives wouldn’t relocate to. Second, make a point of snapping the suspenders of those in your peer group at work to expose them as ass-kissing sycophants. This will make you popular with your co-workers and unpopular with the ass-kissers. Finally, sarcastically yet vigilantly refer to your bootlicking, suspender clad co-worker as Thurston and ensure that all other co-workers know this refers to the British manufacturer that has outfitted kings, presidents, princes and film stars in suspenders since 1820. This bit of corporate frivolity will clean out the climbers and make for a better place to work. Like Gordon Gekko said and Sun-Tzu before him, “Every battle is won before it is ever fought” so snap to it.

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#85 - Enormous Fancy Hats

#85 - Enormous Fancy Hats

Enormous Fancy Hats
Price: Vitamin D Deficiency

Among the many things that rich people like to own, gigantic floppy hats are among the most baffling. Unlike other fashionable accoutrements, intended to flatter a wealthy belle’s beauty, the hat hides rather than showcases the extensive plastic surgery that the trophy wife has undergone. In fact, when matched with the perfect pair of oversized Chanel sunglasses, one’s collagen-injected lips are hardly noticeable. So what’s the point? Why wear a hat with a two foot diameter laden with flowers large enough to make Keukenhof appear unimpressive? Simply put, just as a wealthy gentleman drives an Italian racecar to proclaim his manhood, women wear hats to trumpet their sense of fashion and signal that they are the alpha female in the group. The only way to remain queen bee among the swarming masses is to outdo one’s social circle by purchasing and bravely wearing larger and more ostentatious headpieces than the other ladies at the club.

It may appear that hat fashion ebbs and flows, but just because Aunt Sally didn’t wear her gigantic peacock feathered Easter hat for Sunday mass doesn’t mean that the cultural elite are taking their cue to pack away their hat boxes. In fact, the true barracudas of the runway have already been recounting to which event each woman in her social network wore which hat. After creating a complex social matrix where hats and events are matched, the mad hatter will predict what the ladies will showcase this season and carefully select the latest and largest hats from small boutiques around the globe for her upcoming calendar. This ensures she will never be embarrassed by donning an Albertus Swanepoel from Barney’s during a weekend jaunt to the Hampton’s. Most women in NYC still recall the horror of seeing Mrs. Eleanor Thomas of the Upper East Side standing next to Ms. Mandy-Anne of Kansas wearing identical hats. Unfortunately for Mrs. Thomas she opted for wearing last season’s fashion and Mandy-Anne had just finished a day of shopping at Century 21. Thomas’ agoraphobic fate was sealed when innocent Mandy-Anne asked Eleanor “Did you buy yours on sale too?”

As always, what matters is how to use this to your advantage. Just as Keanu Reeves could not be unseated as “the one” during the 90’s, you should not strive to occupy the throne reserved for a hat aficionado. Instead, opt to go big but not enough that you will clash horns with Chiquita Banana. Flattery will get you everywhere with the Queen Bee and while no less that 24 inches of couture circumference means you won’t recognize her, you will nonetheless be able to pick out her horn of plenty in any crowd. A well placed compliment on her style will go far but delivery is paramount. When approaching, keep your eyes averted and never look her directly in the eye. She will recognize this as respect and allow you to proceed. Next, let her know you love her style. Never tell her you could not wear such a beautiful hat as she already believes that to be true and by stating it you are implying that you think you could be in the same league as her. Instead, let her know that it is the perfect hat for her. She will recognize that you accept her as the alpha female and may at this point compliment your hat. A polite thank-you will suffice and you should offer to fetch her champagne or Iranian caviar to show your gratitude. If she accepts you are part of her entourage. Finally, never make reference to Dr. Seuss or Alice in Wonderland in her presence, she will take it as a personal slight and you will feel her social wrath. Remember, hell hath seen no fury like a woman scorned.

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#84 - Designer Cupcakes

#84 - Designer Cupcakes

Designer Cupcakes
Price: $36 a dozen

Prevailing wisdom dictates that little girls are made of sugar and spice and everything nice. Spend some time in a trendy shopping district and you will soon find that this is largely due to designer cupcakes, emphasis on the sugar and light on the nice. Thankfully, for the financially endowed, they need venture no further than around the corner in their hybrid SUV to satisfy a craving that used to take their private chef as much as an hour to whip up. Designer cupcake shops are becoming so popular, they are threatening to supplant Starbucks as the storefront voted most likely to replace a former tenant, although Vietnamese nail salons run a close third.

While common people may purchase these single serving delights at the supermarket, this could never satisfy the sophisticated sweet tooth of a high net worth individual. For starters, store bought icing isn’t rich enough; cupcake shops appear to have cracked the age old problem of condensing a full pound of butter into a half pound of icing. Second, buying a dozen chocolate cupcakes is blasé; the baked pleasures of the wealthy deserve creative names like “Tickled Pink”, “Lady Baltimore” or “Dirty Blonde”, the latter may also describe one’s third wife. Finally, the creativity doesn’t end with naming cupcakes, rich people love to fawn over the playful shop names where they purchased these heavenly indulgences; think Babycakes, Buttercup and Flour Girls for starters; I adore the t-shirts from Babycakes in NYC.

While many quirks of the wealthy are out of reach of the common man, a love of rich desserts is a human condition that knows no economic boundaries. With this in mind, impressing the wealthy is simple when done by the dozen. Discussing your favorite cupcake shop will certainly do in a pinch but it is the gift of cupcakes that will truly impress. The elegance and tastefulness of ribbon wrapped sugary goodness will have your hosts beaming at your thoughtfulness and once it comes to naming these savory delights, they will figuratively if not literally be eating out of your hand. An excellent conversation starter, your affection for cupcakes will win hearts, minds and stapled stomachs. Be sure to save the “Sexy Red Velvet” for the beautiful heiress you’ve been watching and she may turn out to be your sweet temptation!

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