Some of our readers have expressed concern about the liability of dressing too well—particularly better than one’s boss. Common wisdom says that if you dress better than your boss, you risk his/her ire or jealousy, so you should dress down. I agree, but only if your ambitions go no farther than being a subservient cubicle drone happy with a stagnant but secure job. But if you want to earn your boss’s job someday or one like it, kicking up your personal style is a guaranteed way to distinguish yourself from your rivals.

Sure, you might tick off your boss. Sure, your co-workers might call you a dandy or even a pretentious fop behind your back, but I’ll bet they will secretly admire you as they try to conceal their envy for your eye-catching cufflinks, crisp white dress shirt, and what Forbes.com called "One of Ten Shoes Every Man Should Own" - Toschi’s Berta.

I say:  Don’t dress like the man you are; dress like the man you want to become.

Dressing well is a subtle but powerfully symbolic act of male aggression, but that’s what business is all about—cut-throat competition, balls and brashness, vigor, and survival. J.P. Morgan didn’t have a lot of friends. There was a reason for that. He didn’t want friends. He wanted big-money and all the status that accrues to a man of power. He never ever dressed down.

In our own time, you’ve never seen Donald Trump in a track suit. He’s always in a pricey suit and big phallic-y ties. He’s the Man. Or he thinks he’s The Man. Even though he might not be, he acts the part every day, every night, brushing off ridicule about his hair, his ego, and those God-awful gaudy ties as if they were merely so much lint on his lapel.

To win in business and in life one must not feel guilty about one’s prowess, strength, and talents. Naked ambition should not cause shame. Naked ambition should be clothed in the finest suits and accessories you can afford. Think of it as armor. Style is a gentle but powerful weapon for the man who insists on success. He’s not sitting around waiting for his “big break.” He’ll make it happen himself, some way, somehow.

And if your boss doesn’t like it, then you’ve successfully exposed a weakness you can exploit. If he fires you, then you weren’t going anywhere in that firm anyway, so it’s best you find a work environment that appreciates your strengths rather than regards them as a threat. Just remember to tip your hat to your ex-boss as you head out the door on your way to greener pastures.

These days it’s nearly impossible to find a good martini. And it’s all James Bond’s fault. He popularized the vodka martini and gin became as unhip as a handlebar mustache. Cocktails, like clothes, are as much governed by fashion as they are by taste, so I am pleased to report, that the classic martini, “the elixir of quietude,” as E.B. White called it, is making a comeback. And here’s how to make it the modern gentleman way...[Read More]

Perhaps as a "start-up" ourselves, it is with added sadness that we read about good ideas that come to an end. On Sunday, Eos Airlines filed for bankruptcy after 3 years of service and $200M+ in equity capital raised. Its final flights operated today, Sunday.

Most of the country has probably never heard of Eos, mainly because it had a very focused, niche business model. The airline's concept was to turn a Boeing 757 -- which most commercial airlines fill with over 200 passengers -- into a jet for just 48 business travelers who would fly from New York to London in style. One class. One round-trip route. It seemed like a good idea.[Read More]

Last week, we explored a question at the intersection of On The Fly's point-of-view and my book: Was Cary Grant a "modern gentleman"? It’s an intriguing question because Ami would consider Mr. Grant an icon of "Old School" style -- an actor who not only made movies during Hollywood’s golden era but who epitomized it. And that was a very long time ago.

But the arc of his life, from Archibald Leach, a poor and awkward kid from the English provinces, to the suave movie star at the top of Hollywood’s A-list, is essentially a story about a very modern obsession— the makeover.

By dint of a shrewd understanding of the transformative power of style—and by style I include not only how he wore his suits and ties, but how he walked and talked, where he spent his days off, and the quality of his mind and character—he became the man he wanted to be, a change so profound it is, I believe, largely the reason for the continuing interest in him as not only a movie star but as an historical figure.

His journey is one from which we all can learn—not as a dry academic exercise but as a kind of entertaining guide that reflects our own interests and goals. One of which is the quest for the best and most tantalizingly unique products at the best value.

In Grant’s day finding the best but not necessarily the most expensive objects was truly a quest, an abiding passion that meant exploring the shops and showrooms in cities all over the world.

Visiting Rome, he discovered the luxurious bespoke suits of Caraceni. In Milan he selected cashmere and silk sweaters by Pasquale Avon Celli, a genius with fabric who made a splash in the 1920s with his silk three-button polo shirt whose legendary quality was achieved by the importation of looms with 36 needles that were then only used to produce women’s stockings.

Grant, most notably, wears a long-sleeved striped Avon Celli polo in “To Catch a Thief” which he paired with a red foulard for one of the most memorable looks in film history.

When in London he visited Aquascutum for one of their signature rain coats, Hawes & Curtis for a new glen-plaid suit, Lobb or Tuczek in Mayfair for a fitting with the legendary George Cleverley who might make him a new pair of benchmade tasseled loafers, and then off for window-shopping in the Burlington Arcade, searching its shops for the new and the novel, from hand-crafted chocolates to a nifty new pair of cuff links. 

His scents were selected from Floris, Creed and Aqua di Parma. In New York he might make a stop in Brooks Brothers for one of their off-the-wrack button-down white shirts he liked so much. Then to Tiffany and Verdura whose help he enlisted for the jewelry he designed specially for his wife Barbara.

Later in his life he discovered shirtmakers and tailors in Asia and his garments would travel back and forth from Beverly Hills to Hong Kong with alteration instructions until the garments met his exacting standards. Adjustments of 1/8th of an inch on a shirt sleeve were not unusual.

Accumulating a fine wardrobe was far more perilous than it is for fans of On The Fly. When the Andrea Doria sunk off the coast of Nantucket on July 25, 1956, Grant’s third wife, Betsy Drake, was onboard with a batch of his custom-made shirts that she was transporting from Europe. Betsy was rescued but his shirts went down with the ship.

There were far fewer luxury brands then than there are today, so there were far fewer choices, and of course they were not nearly as accessible for him as they are for us, thanks to the wonders of technology.

Perhaps the image we have of Grant is one of staunch conservatism, a man dressed more like a banker than a daring sartorialist. (It’s that damn gray suit in “North by Northwest”!). But this is not really accurate. He was very cutting-edge, very forward-thinking in just about everything he did. 

Was Cary Grant a modern gentleman? Indeed he was. In fact, I think he had what I would call the essential quality of the modern gentleman—a passion for style, innovation, and quality that is shared by fans of On the Fly who explore this site not as a chore but as a joyful journey, though one without all the travel expenses Mr. Grant no doubt incurred. 

Versace did it. Armani did it. Other designers have thought about it, or talked about it. And last night, Mulholland Brothers, based in San Francisco, unveiled The Mulholland Suite at the Huntington Hotel in San Francisco's Nob Hill neighborhood. Mulholland loyalists know that the company dabbled in the furniture business for a few years with a beautiful line of what we called "boldly masculine" pieces in dark wood stains with complementary leather accents. That, and their particular expertise in leather goods, inspired the design of the suite.

[Read More]

More than a year after my biography, “Cary Grant: A Celebration of Style,” was published, and after writing more than a few articles about him during that time, I return again to the topic.

But I do so not because of any obsession with the iconic movie star or lack of interest in a new subject or even to shamelessly plug my book. I do so because Cary Grant is of enduring interest to you, the movie fan, the sartorialist, the connoisseur, the keen-eyed shopper.

Rarely does a day go by that I do not receive a question about him sent to my web site email address. The appetite for information about him seems insatiable, a testament to his timeless appeal and his mystifying achievement as a man of style.

The questions are far ranging, running the gamut from the arcane, such as, ““How much starch did he like in his shirts” (very little), the merely curious, “Which brand of watch did he wear?” (Cartier) to those typical of film fans, such as, “Who was his favorite actress?” (Grace Kelly).

But the question that interests me now is one posed by On the Fly founder & fellow blogger, Ami Arad: “Was Cary Grant a modern gentleman?” For the answer, tune in next week...