With the gape in his shirt collar, the 1970s-sized bowtie, and industrial-sized watch, musician Nick Cannon is ready for the prom, not an awards show. 

Although few still follow it, there is a hoary rule that a gentleman never wears a watch with formal wear—after all, on those occasions he would never need to take notice of the time.

Izzy pities 72-year-old Giorgio Armani in his refusal to dress his age, which bespeaks a denial of his own mortality.

Likewise, if the clothes make the man, then François Girbaud is an angry adolescent—excepting of course his camera, which he wears like a middle-aged tourist.

The Manolo has noted outgoing Prime Minister Tony Blair’s revelation that

he had worn the same pair of shoes to his weekly question-and-answer session in parliament since he became the country’s leader.

The shoes in question — an 18-year-old pair of hand-made leather Brogues that have only been re-soled once — were made by Church’s in Northampton, central England.

“I know it’s ridiculous, but I’ve worn them for every PMQs (Prime Minister’s Questions) … I’ve actually had them for 18 years,” Blair told The Times in an interview, adding that “cheap shoes are a false economy.”

As the wise adage has it: Women brag about their newest clothing purchase, men their oldest.

In constrast to Ralph Nader, who has worn the same pair of army boots for decades, Blair’s choice of footwear is beyond reproach, and certainly not evidence of an unhealthy asceticism (so common among self-proclaimed saviors). 

The Prime Minister has come along way sartorially since his Oxford days.

For the story behind this bowdlerized photograph, as well as the full original image, which is an incredible depiction of the aristocracy at play, go here.

The Sartorialist took some great photos at Pitti Uomo, the famous men’s ready-to-wear show in Milan. 

This distinguished-looking, no doubt Italian gentleman is casual but debonair in an unconstructed jacket that appears to be made of linen and/or cotton.

Accoutered in a peak-lapelled suit of sumptuous cloth, Valentino CEO Matteo Marzotto looks like the merchant prince he is.  (Note how the color of his pocket square pops out.)

And GQ deputy editor Michael Hainey show you can get away with a too-tight jacket when it’s clearly intentional.  (The hair helps, too.)

When it comes to formal wear, the only truly acceptable shoes are opera pumps (for your inner Louis XIV) and patent leather lace-ups.  Made in England, the glossy pair above is now on sale at Brooks Brothers.

For tasteless frat boys everywhere, this hideous pair of shorts from Matix is designed to carry a six-pack of beer in its four insulated pockets.  Combine it with a beer hat and a camel-sized hydropak, and you’ll never have to leave the couch ever again.

Izzy feels remiss for having offended some of his loyal readers regarding Gianfranco Ferre.  The post was intended to make fun of the designer’s fondness for white suits—not his size and certainly not his passing.  (As someone who has actually read Moby-Dick (twice!), Izzy feels confident that while being compared to a whale can be unflattering, the allusion to the Great White Metaphor has many positive connotations.)

As a matter of fact, Izzy admired Ferre for being someone in the weight-obsessed fashion world who demonstrated a (stereotypically Italian?) willingness to take pleasure in food.  Come to think of it:  Could the widespread abuse of intoxicants in that industry be  an attempt to compensate for self-denial?

In any case, Izzy apologizes for teetering over the “Cartesian vortices” below.

Gianfranco Ferre, the Italian “Architect of Fashion,” has died. Captain Ahab must have finally caught up with him.

Modelled on the guts of vintage watches, these cufflinks put a different kind of jewel on display.

On the other wrist, this “internal watch” is perfect for the man with all the time in the world.  Either that or smothering fantasies.

Izzy recommends the soft-shoulder look for those who can get away with it, a group which, unfortunately for him, doesn’t include David Hyde Pierce (here posing with his recent Tony Award).  Unless he plans on mastering the military press at the gym, he needs a jacket with some padding to bring his shoulders closer to horizontal.

Displaying a flesh-colored hand, Valentino proves himself to be at least partly human.  Kind of like a reverse Luke Skywalker.

Vowel-challenged streetwear label UndrCrwn is selling a seersucker tracksuit, the perfect crinkly accompaniment to these sneakers. 

Although the brand is LA-based, Izzy wonders whether their name was inspired by this Czech and Slovak tongue-twister, meaning “stick finger through throat.”