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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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#76 - Tartan Print Pants

#76 - Tartan Print Pants

Tartan Print Pants
Price: Wool Itch Where You Want It Least 

If eggnog, mistletoe, tinsel, Grandma’s flask and the lingering scent of pine needles sounds familiar, you know the holiday season is upon us. In many households, Dad’s tattered and occasionally revealing terrycloth robe has contributed to psychological trauma during the holidays, in other homes it is Mom’s “blackened” turkey that has scarred the children’s memories. For the children of rich people, the ghost of holiday trauma manifests itself as the donning of tartan print pants. These holiday favorites are thought to strike the perfect balance between formal and festive but in fact walk the line between hideous and ridiculous, more so for families without a hint of Scotsman in their storied lineage. 

Traditionally, tartan prints have bound clans and identified kinsmen to one another through the intricate patterns designed exclusively for their family name. As the Scottish boast an unrivaled history of war, the tartan played an integral role in identifying the unrecognizable fallen warriors of battle. Today, far from the vaunted lochs and moors of Culloden and Bannockburn these same tartans, as pants not kilts, represent cliché advertisements and the mark of a healthy net worth. For the wealthy it is a subconscious announcement that they are loud, proud and can make any item fashionable by spending excessively. In fact, there are fashion historians who believe the grunge movement in Seattle and today’s explosion of plaid prints at leading American clothiers can be traced back to a tartan cummerbund worn during holiday festivities hosted by the Vanderbilt family on December 19, 1872. This brash display spawned a “fashion” revolution despite the underlying rationale; young Alistair chose tartan over haggis following a lost wager to a member of the MacLean family. 

Nonetheless, tartan prints are an excellent means to kick start a wealthy friendship. While purists would recommend honing your ability to identify the more than 13,000 tartan patterns, this is time consuming and frivolous. It is highly unlikely that your plaid sporting friend’s knowledge of Scotland extends beyond Braveheart, whisky and the Loch Ness Monster and could not identify the tartan they are wearing even if you could. In fact, it would make them uncomfortable if you asked them anything about the history of their woven cloth given their ignorance of the topic. Instead, draw on the strength and power that a tartan represents. Asking if wearing such a print reminds them of their own success and prowess in life could be magnificent. You will be tiptoeing through the DMZ that separates blatant brown nosing and world class flattery but when it works it really works! Fine tune this skill and you’ll be sipping single malt with the upper crust, otherwise you will face the social guillotine without the historical significance attributed to Mary Queen of Scots. Tha mo bhàta-foluaimein loma-làn easgannan! 

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#58 - White Pants

#58 - White Pants

White Pants
Price: No Condiments or Red Wine

As summer draws to a close, the sun finally sets on another season of rocking the white pants. Labor Day is just around the corner so it seems like the right time to reflect and revisit questions like “dude, what the f*&k are you wearing?” While women will always have a classic elegance when wearing white pants, men will always have jokes made about them when wearing white pants. That is unless they are professional athletes in uniform, sailors in uniform or male nurses in a psychiatric ward which brings up an entirely different list of questions.

While rich people love wearing white pants they know it is wrong. At some point between deciding to wear them and complimenting their own posterior in the mirror they realize that they are about to spend an entire day looking like Captain Stubing’s cabin boy and still they walk out the door to their freshly waxed Range Rover. Knowing that rich people love being right, they spend their short commute prepping why white pants are a must-have wardrobe item to counter snide remarks from the likes of Hunter in Sales. Explanations range from “knowing fashion” to “it keeps me cool by reflecting the sun” and if required “I’m sailing with Jim from Oracle this afternoon”.

None are convincing arguments that sway anyone towards considering white pants as a good decision but the desire to evade a half hour lecture on why white pants represent culture means nodding one’s head and quickly departing in the opposite direction. The explanation for white pants is simple; to flaunt wealth. Just as middle-class kids wear skirts over their jeans to illustrate that they have more clothes than they know what to do with, rich people use white pants as a way to showcase their disregard for practical choices. A typical pair of white pants will last for two and a half uses before coffee, wine, mustard, grass or fresh berries deflower the pants and render them useless. This gives their owner the opportunity to flippantly disregard the accident and quip “c’est la vie” indicating his $395 Michael Kors mean nothing. This impending incident adds excitement to the buttoned-down, conservative elite as the inevitable stain is like Russian roulette for the fashion conscious. That said, Czar Ivan the Terrible would have justifiably shot any man in his court for wearing white pants.

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#37 - Pure White Bathrobes

#37 - Pure White Bathrobes

Loro Piana Cashmere Robe
Price: $3,495

Rich people face a never-ending dichotomy, an inner turmoil that is rarely understood by the middle and lower classes. How does one balance a public image of importance and responsibility with a private life of leisure and luxury? Remember, their time is precious and it should be spent increasing wealth or enjoying life to the fullest. While yacht charters, island getaways, topiary and escort services are all important, the most accessible way to enjoy a luxurious lifestyle is the white bathrobe. Of course it helps if your major domo is serving fresh squeezed orange juice, Italian espresso and a selection of tropical fruits while you work through the NY Times crossword, in pen of course, but these are secondary to the primary luxury that a robe provides.

To befriend the rich, you will want to familiarize yourself with the comfort and luxury provided by this simple item. I know what you are thinking, my father wore a threadbare robe every Sunday morning and he definitely wasn’t rich. Don’t be fooled, there are robes and then there are robes. Any jackass can visit Target and pick up a terry cloth striped robe with bunny slippers for less than twenty bucks but these betray the essence of the real deal. A robe should be thick with plenty of material to wrap and long enough to avoid errantly displaying the family jewels. Next, you will notice the difference in the collar; luxury demands that a second layer is stitched on the inside to ensure you are swaddled in plush fabric around the neck and chest. Finally, deep pockets are required. You may wonder…what would I carry around in the morning? The answer is nothing; they act as a metaphor to remind you that you are rich and can afford frivolities like meaningless pockets.

Should you find yourself in conversation concerning morning couture, sharing breakfast with a wealthy colleague at the summer home or enjoying a steam bath at the club, it is wise to be versed in the subtleties of leisure wear. Debate continues around where one should acquire this essential apparel. To many, the only choice is a pure white robe from a high-end department store or local boutique specializing in fine linens and towels. For others, purchasing robes embossed with luxury hotel brands serves a dual purpose of showcasing your worldliness and accessing global luxury through well regarded purchasing departments. The danger with the latter is the lingering question of whether the robe was purchased or gauchely abducted from the Four Seasons without a second thought. For this reason above all others, err on the side of social acceptability and avoid branded robes, unless you are Winona Ryder of course.

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#36 - Dress Shoes With No Socks

#36 - Dress Shoes With No Socks

Salvatore Ferragamo Puntala Croc Oxford
Price: $2,300

Rich people love fashion. Rich people love beautiful shoes. Rich people love the feeling of soft Corinthian leather, or maybe that’s just life according to Ricardo Montalbán. Regardless, fantasies do come true and every summer thousands of rich people opt to leave their socks at home and slide their sweaty feet into extravagant Prada, John Lobb, Salvatore Ferragamo and A. Testoni shoes to express their carefree nature and show-off their lack of podiatric inhibitions. If you are rich and you wear socks you may as well drive a 1975 Chrysler Cordoba because that’s the level of respect that you will garner but at least you’ll still feel soft leather against your skin from your vintage automobile’s luxurious seats.

For many, the thought of sliding their feet into a pair of brand new shoes with nothing but a smile and a shoehorn is repulsive. In fairness, there are more disgusting habits that a man can pick up in the dirty streets of the world’s finest cities and unlike the aforementioned dirty habits, sans sock aficionados say don’t judge it until you’ve tried it. Of course, if you aren’t rich, you aren’t subjected to ridiculous peer pressure to adopt styles popularized by Miami Vice and other atrocities of the eighties. In fact, average men that show up anywhere in dress shoes without socks are most likely to become the butt of all jokes for the night and likely for the rest of their life. Not so for the rich.

The ability to destroy a pair of shoes with nothing but a thousand sweats glands is a status symbol more than it is a comfort choice. While middle class white kids wear Che Guevara t-shirts and baseball hats with sticker attached to express that they are badass, the wealthy adopt a modest subtlety to show that they have more money than most Caribbean nations. Sockless Italian loafers are akin to standing outside Goldman Sachs’ headquarters and screaming “I just cashed a million dollar bonus check! Screw you taxpayer!” Of course they never would, so they let bare ankles do the talking under their perfectly tailored suit. A quick glance around Madison Ave, Lexington Ave, Fifth Ave and the men’s department of Bergdorf Goodman will reveal them as playgrounds for the sockless masses. A word to the wise, steer clear of Japanese restaurants that require patrons to remove their footwear if you want to avoid the pungent smell of old money at lunch!

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