With only 4 weeks left until the release of the five-months-delayed movie starring Michael Douglas and Shia LaBeouf (pronounced "shy-uh la-buff," by the way), it's time for a peek at what the film's stars will be wearing once it hits screens on September 24th.

But first, I'd like to suggest that you take a look at this excellent post at Clothes On Film for a refresher on the style of the original Wall Street. Remember the eighties: contrast collars, big suspenders, big pleats. And more importantly, remember the difference between Gordon Gekko and Bud Fox. As the linked post points out, Fox starts the movie as a very plain, conservative, Brooks-Brothers-type dresser. As he enters more fully into Gekko's world, he begins to emulate Gekko's flashier manner of dress, particularly with regard to accessories.

So too in the sequel we can see the contrast between Gekko and his new protégé, Jacob Moore. But here, the positions are reversed: Gekko is conservative and dresses like "old money," while Moore is contemporary and dresses like "new money." Just take a closer look at the movie poster up there. Gekko: three-piece suit, bengal stripe shirt, simple dotted tie, pocketwatch. Moore: single-breasted peak-lapel (SBPL) suit, white shirt, Hermès tie.

This nearly seems to be Moore's uniform, at least while he's wearing a suit. Always a SBPL suit, always a white shirt, almost always an Hermès tie. He also favours narrow trouser legs hemmed short with substantial cuffs, and appears to wear nothing but Gucci horsebit loafers with every outfit, including casualwear. And don't forget that white linen pocket square, with its artfully scalloped peaks. Much of Moore's clothing is extremely trendy, particularly the SBPL suits with the narrow legs and the cuffs. His wardrobe selections seem to have been made to reflect the Wall Street trader stereotype, the guy who buys new clothes constantly, ensuring that his wardrobe is both of-the-moment and certain to become dated. I don't want to speculate too much on what Moore's clothes mean for his character's identity without having seen the film. But I think it's worth asking whether he's dressing this way because he feels these clothes really belong to him, or whether he's trying to fit into a world where he doesn't quite feel he belongs. The $38,800 watch he apparently wears has to make you wonder a little bit about insecurity.

Gekko, by contrast, wears many more conservative pieces this time out. You might call it the "rich old white guy" look. In the HD trailer, for example, the sharp-eyed observer will spot a Canali label inside one of Gekko's jackets, a very traditionally-styled (and high-quality) line. And when Gekko walks side-by-side with Moore, the contrast becomes even more apparent: Gekko's jackets have a more conventional, slightly longer, length, with lapels of moderate width (generally notch, not peak), paired with shirts and ties of relatively muted colours and patterns. The pants are plain-hemmed, not cuffed, and fall to a normal length, while the shoes are understated lace-ups.

Gekko's wardrobe still has elements of pizzaz, of course, but they're subtler, and they seem to come out more strongly in his suits than his casual clothes. Photographed for Vanity Fair, he wears a three-piece suit with an unusual double-breasted vest, with even more unusually slanted rows of buttons. In the other photo for Vanity Fair and at right, he wears a chalk-stripe suit (with purple stripes!), purple large-foulard tie, and purple pocket square. The shirt, with its simple striping, anchors everything down and prevents it from becoming totally ludicrous (although I have to wonder whether outfits like this might be regarded in decades to come with just as much bemusement and curiosity as Gekko's eighties trainwrecks originals are today). We even see flashes of flair in suitings: right at the end of the trailer, Gekko is wearing a black suit with a strong but unidentifiable textured fabric. Essentially, Gekko tends to be conservative in the fit and cut of his suits, but brings in more contemporary (and ostentatious) elements in the choices of fabrics and accessories.

Maybe it's just because Gekko's personality is already a known quantity from the first Wall Street, but I think there can't be a doubt in anyone's mind that he absolutely owns his clothes. He takes what's already inside him and projects it outward, making his clothes match his inner self, expressing himself through his clothes. And, though he's saying it in different ways, he's saying the same thing in both movies: "I am in your face and I am bigger than you and I will destroy you if you cross me." But there's also the element of comfort there, the sense of being at home in his clothes.

The question I have about Moore is whether he's doing just the opposite of Gekko: putting clothes on on the outside, and then hoping that they can change what's on the inside. I don't get a sense of personalization from Moore's clothes; it seems like he could be thinking "this is what a trader wears and I need to look like a trader so I need to wear these clothes." It doesn't seem like it could be his personal uniform, so much as it's the uniform of an occupation that he happens to hold at the time. They're someone else's clothes, essentially. I'm interested to see whether this bears out in the plot of the movie itself.

I'd like to close by saying how amused I am that, where the filmmakers decided to ditch Gekko's classic slicked-back hairstyle, they appear to have replaced it with that of another infamous figure in the financial world: Bernie Madoff.

Left, Bernie Madoff; right, Michael Douglas as Gordon Gekko.

(Or, at least, what Madoff would have looked like if he had as much hair left as Michael Douglas does.)

Although it's three years old, I just stumbled on this excellent photoessay from TIME Magazine on JFK's personal style. It's a slideshow of pictures narrated with commentary on what made Kennedy's style so unique and influential. And it occurred to me as I was looking at these pictures that JFK's style can be seen as a combination of two huge trends in men's fashion over the last 3-4 years: traditional Americana/prep, and the '60s revival brought about in large part by the TV series Mad Men.

Left, President John F. Kennedy; right, Mad Men's Don Draper.

Look at above picture—the entire JFK slideshow, in fact—and you'll see the building blocks of Don Draper's wardrobe: narrow lapels, narrow ties, white shirts with small-proportioned point collars. But also in those pictures, especially the more casual ones, you'll see the foundational elements of classic American sportswear: button-down shirts, polos, crew-neck sweaters, khakis, sneakers, Ray-Bans.

Left, JFK; right, a page from the J.Crew September 2010 men's catalogue.

These elements are as close to timeless as you can get. They're the basic staples of the American man's wardrobe. They may pass in and out of fashion, but they are never out of style. GQ even went so far as to compile a list of "10 Things That Will Never Go Out of Style," and, while I think that it's a little too early to make a judgment call on Timberlands, I don't seriously disagree with the rest of the items they list. (Ray-Ban Wayfarers have made a rather tragic hipster comeback lately, but hopefully they'll soon return to their roots.)
Now you may argue that it's facile to compare Kennedy to a J.Crew catalogue when J.Crew doubtlessly draws conscious and perpetual inspiration from Kennedy, but in a way that's exactly the point: you can't draw perpetually from Kennedy unless there's something timeless about his clothes. And these staple clothes are the ones you'll always be able to find in stores. You could do worse than to build a wardrobe around them.

As for Mr. Draper, it could be said that the '60s skinny-suit trend is really just an iteration of the skinny-suit trend that started with Hedi Slimane and Dior Homme in the early 2000s. Really, how long were D&G (and H&M, for that matter) doing narrow lapels before Mad Men came on the air? But the Mad Men look is a little bit different: the jackets are slightly less fitted, the closures somewhat higher. The Dior Homme look was more about leanness and length and androgyny; the Mad Men look is vintage '60s, when men were men, and even a refrigerator-shaped gentleman could get away with a slender tie and lapels. I'd caution anyone against embracing it too fervently, since the pendulum is bound to swing back the other way, but I personally have one grey pinstripe slim suit from H&M in my wardrobe, and it's great fun to Draper it up with a white French-cuff shirt and a skinny black tie every now and again. All you need to top it off is a pack of Luckies, two fingers of rye, and of course, the right gel. Smashing!

...or at least, smashed.

You can always count on a pocket square to add flair and panache to an outfit. (I hope I don't have to tell you how to fold one. If so... I'll look the other way while you click here.) I get a little self-conscious wearing a pocket square to the office, though; I worry that anything other than the plain single-fold might come across as too flashy, even uppity. But one day, I had a wonderful stroke of luck while trying to achieve that perfect devil-may-care spray of asymmetrical points:

Pocket square, Hugo Boss. Jacket, H&M. Shirt, Tristan. Tie, vintage.

Such a unique shape! But what on earth was it? At the time, I thought it looked like the Guggenheim Museum in Bilbao, Spain:

But only today did I realize that this impression wasn't accurate. What it actually reminded me of was a piece of furniture: the "Tatlin" sofa, designed in 1989 by Mario Cananzi and Roberto Semprini, and manufactured by Italian furniture company Edra:

Cananzi & Semprini's design was based on a tower designed (but never constructed) by the Russian architect Vladimir Tatlin. The sofa might already be familiar to you if you're a Star Trek fan; it featured prominently in the Next Generation episode "The Most Toys," where it belonged to the unscrupulous trader and collector Kivas Fajo.

As for the pocket square? It was raining that day, and by the time I got to the office and took off my trenchcoat, the fold was ruined. I could've probably tried for half an hour and still not succeeded in duplicating it. Maybe someday I'll figure out how to do it again...

I've been writing a lot of personal thoughts and musings here in my first few entries, but I also promised to provide some concrete style rules for you guys. The most stringent rules for propriety in dress come, not surprisingly, in the world of suiting. They require significant study, care, and attention to detail before they can be mastered, which is why I've devoted a lot of time to learning about suits and their related accoutrements. So now it's time for a bit of practical advice. In no particular order:

1. Size does matter.
You need to know your size. This really should go without saying, but I can't count the number of times I've asked a guy what his jacket size is and had him tell me one way or another that he had no idea. Here's what you do: get a tape measure. Even a metal one that you'd use for measuring wood will work. Wrap the tape measure around your chest at its fullest point, usually right around the nipples. The measurement in inches is your jacket size. And chances are, if you subtract 6 inches from that, you'll get your waist size. This is how a standard suit is sized; the difference between the chest measurement and the waist measurement is called the "drop." 6 inches is the standard drop for men's suits.

Once you know your chest measurement, knowing what length of jacket (regular, tall/long, or short) to purchase is fairly straightforward. The two rules of thumb are (1) the jacket, like a good lawyer, should cover your ass, and (2) the hem of the jacket should fall roughly even with the knuckle of your thumb when your arm is at your side, though many jackets today may be an inch or even two inches shorter. Generally, if you're between 5'8" and 6', you'll probably take a Regular; outside that range, you should try both Regular and the other to see what looks best.

2. The most important fit is not the chest, but the shoulders.
Having said all of the above, the first thing you need to look at when trying on a suit is the fit of the shoulders, because in spite of what the salesman may tell you, shoulders cannot be tailored. The entire jacket is constructed around the shoulders; they are the garment's foundation, and if they don't fit, forget it. How do you tell whether they fit? The outermost point of the shoulder should not extend beyond the muscle of your upper arm. You can test it this way: if you stand perpendicular to a wall and edge sideways towards it, the shoulder of the jacket should not touch the wall before the rest of your arm does. If the jacket fails this test, go down a size. Generally speaking, if the jacket makes your shoulders look broader than they actually are, it's not a proper fit.

3. Tapered waists aren't just for women.
I will never forgive the salesman at Moores who, when I suggested that the waist of my first suit jacket needed to be taken in so that it curved closer to my body, told the 18-year-old me that "only women's suits do that." WRONG. A man's jacket should not hang straight and shapeless from his underarm to his thigh. Although suits have been cut this way from time to time over the last century, notably the "sack" suit popularized by Brooks Brothers, this shape doesn't flatter the body at all. Speaking in terms of ideals, men are supposed to have shoulders that are broader than their waist; essentially, a triangular-shaped torso is the most desirable. To create this shape (or the illusion of it), the jacket must taper in at the middle, contouring to the wearer's body so that the waist appears smaller than the shoulders and chest. This is known as "waist suppression." And regardless of the man's actual shape, tailoring a jacket this way makes him look better.

4. You need a good tailor.
It's highly unlikely that a suit will fit you perfectly right off the rack; at bare minimum, you'll have to have the pants hemmed. But it'll probably need a lot more work than that if you want it to fit like the ones you see in movies. The good news is, though, that if the jacket is a bit baggy, its sleeves are a bit too long, or the pants are a bit too big, a tailor can fix them. (Personally, my spine is little too straight at the top, so I always get a roll in the back of my jackets just below the collar that has to be corrected.) Having said that, tailoring can get expensive, and remember: he's a tailor, not a miracle worker. If the suit jacket is totally the wrong size, a tailor can't fix it. (Pants, yes, if you're prepared to pay for them to be taken apart entirely and basically re-cut into a new pair, but even then you can probably only go down one size.) The general rule is that it's usually possible to take something in, but it's not necessarily possible to let something out, because the extra fabric may simply not be there.

5. Money isn't everything.
I've heard it said many times: a $400 suit that fits properly looks better than a $2400 suit that doesn't. If you have the knowledge to properly instruct your tailor, you can make a cheap suit look pretty damn good. Sure, a $2400 suit is very nice, but if you have to wear one to the office every day, it becomes rather cost-prohibitive. Personally, as far as the lower end goes, I really like Club Monaco and Zara. They both have great designs at a sub-$400 price point which, importantly, usually come in 100% natural fibres (wool, cotton and linen). If there's one minimum standard I would advocate for a suit, it's the 100%-natural-fibre rule. You often find polyester in cheap suits at places like H&M, Le Chateau, etc., but wool is superior in every way, primarily because it looks better and wears better.

And there you have it. Coming soon: specific ideas to get more mileage out of your existing suits, using tailoring and accessories. Questions? Leave a comment!

Vanity Fair has excerpts from various sections of the upcoming book True Prep: It's a Whole New Old World, written by Lisa Birnbach as a sequel to her 1980 bestseller The Official Preppy Handbook. TOPH (a complete scan of which can be found here) was apparently originally intended to be a humour book, but over the years many have adopted it as an earnest guide to creating the ideal preppy lifestyle. Sadly, the book is now significantly outdated, with all its meticulously-researched addresses, phone numbers, and postal rates having become all but useless to the modern reader. Combine that with the recent resurgence in preppy style and the fact that the original is long out of print, and is it any wonder that a sequel should arrive? 

True Prep is essentially conceived as an update of the original, to reflect social changes that have occurred in the last 30 years. For example:

If, in 1980, you had whispered to friends that within the next few decades America would elect a thin, black, preppy, basketball-playing lawyer to be president, they would have laughed at you and exhaled [smoke] in your face, inside the restaurant or club where you were sitting.

Now, contrary to what you might first assume, TOPH wasn't just a style guide, but an insight into an entire way of life, covering not only the "correct" schools, sports, decor and pets, but also delving into more abstract topics, such as attitudes and manners. The excerpts from True Prep show that it contains the same breadth of coverage as the original, discussing not only the pedigree and size of logos on polo shirts—unquestionably a topic of grave concern—but also matters like demographics, career choices, and the importance of frugality.

I'm hugely looking forward to this book. Not having been "to the madras born," as it were, it's hard enough to understand true prep even with the assistance of TOPH, let alone trying to figure out what it means to be preppy in 2010 rather than in the '80s. But of course, as this is a style blog, I'm most looking forward to their thoughts on changes in preppy clothing, particularly those "recent prep brands we are forced to recognize." What are the fates of J.Crew and Ralph Lauren? Inquiring minds want to know! And I, for one, am placing my pre-order ASAP.

I'll leave you with a True Prep Preppy Playlist, courtesy of publisher Knopf Doubleday.