In the post-Bogart age, the fedora is a double-or-nothing wager that will land you in the losers’ circle far more often than it will pay out. But for guys who can back up the bet, the returns can be handsome. You’ve seen Brad and Johnny carry it off. Perhaps you’ve watched Mad Men’s Don Draper toss his felt aside after walking into a room like he owns it and thought to yourself, I could make that work. Maybe you went so far as to buy one. But beware the hat trap. Before you venture out”"to a place where a chapeau isn’t required by a costume theme or as a prop to distract paparazzi”"consider how that fabric atop your head will define you.

Click on Jude Law to see a Details slide show

“You have to feel like you own that piece,” says Kevin Harter, men’s fashion director at Bloomingdale’s. But confidence can take you only so far; a false tip, a clumsy doff, or an incorrect fit can render your cap dunced. If you’re in your twenties, there’s a chance you can get away with the casual fedora, as long as you keep what’s south of your chin simple. Avoid necklaces, graphic T-shirts, and vests, which, when paired with a hat, may cause a chemical reaction that results in Pete Wentz. If you’re in your late thirties or early forties, a classic gray fedora can be a smart and practical partner for a suit, provided you stay away from ridiculous embellishments. Shape, size, and positioning make all the difference: A fedora shouldn’t be perched high on your crown or squashed down on your brow. It should frame your eyes but not hide your face. “Stick with smaller brims,” says Banana Republic creative director Simon Kneen, “or you run the risk of looking like Oscar Wilde.” And while a gentle tilt is acceptable, cocking at an extreme angle is strictly for Dick Tracy.

Still think you have what it takes? Go for it. If not, try flipping the hat over and asking for change.

Written by Courtney Colavita. Article used with permission.

The creative director at Marni on male vanity, the importance of modern suits, and the perils of ugly shoes. 

1. A man has to discover his own taste and then base his sartorial decisions on that-you shouldn’t buy something because you saw it on TV. You need to feel at ease in your clothes or you risk being a bit ridiculous.

2. I like a guy in a suit that’s cut a little smaller-slightly shorter, with smaller lapels. Inside, the jacket should have beautiful finishing that only the guy wearing it notices.

3. Italian men are very vain, even if they won’t admit it. They care about their style.

4. Not everyone looks good in a tuxedo. It’s important to look at proportions and find one that fits you well.

5. Shoes define the kind of man you are. They should never be too trendy or showy but lean toward the classic. There are a lot of ugly shoes out there, and they can ruin even the most sophisticated attire.

6. A little bit of chivalry always makes a woman happy. You shouldn’t exaggerate, but I do like it when a man holds the door open for me. I think, Okay, this guy has manners and knows how to comport himself.

7. When it comes to wearing color, you need to be a bit careful-a bit more traditional. A man should look sophisticated and refined, and color can sometimes get in the way. You have to be moderate.

8. Men can carry bags as long as they are masculine, like a tote or an attach© case. Look for a sturdy canvas or handsome leather one, maybe with a raw finish. A bag should be functional and practical.

9. Clothes don’t necessarily render a man sexy-his attitude and his nature do. For me, someone who is not classically handsome but has a lot of charm is more attractive than a really good-looking guy with no personality.

10. My husband’s style is classic, but he’ll occasionally wear a Marni sweater or sneakers with a suit or try a jacket that’s slightly shorter, and it works for him. My son is more daring. The most important thing is to be yourself.

Check out these top stories from Details:
FOLLOW THE RULES: LUCAS OSSENDRIJVER
Lanvin’s inventive men’s designer on the merits of sneakers, the tackiness of logos, and why you should invest in a mismatched suit.
FOLLOW THE RULES: V‰RONIQUE NICHANIAN
The menswear designer at Herm¨s on the myth of French style, avoiding trends, and why you can never have too much cashmere.
FOLLOW THE RULES: PAUL SMITH
The sharp British designer on poorly dressed Londoners, Daniel Day-Lewis, and when you should lose the bow tie.

Our friends at Details Magazine present a few simple fashion rules from men’s designer Lucas Ossendrijver.

1. You shouldn’t adapt to what people expect you to wear-you should make your clothes your own. For me what’s interesting is to wear the jackets and pants of suits separately.

2. I think it’s distasteful when people buy clothes with logos or brag about what they spend on their clothes. Luxury should be something intimate.

3. Jewelry is very difficult for men, but they can go a little more extreme with shoes and bags. Wear trainers with a suit and the look completely changes.

4. I think clothes are more elegant when they’re nonchalant. You can wear something quite sophisticated but not look too overtly luxurious.

5. Friday-wear is very typically American. You have this office uniform, and then suddenly it’s the weekend and it’s the opposite. I think it’s better to mix the two and make officewear a little less formal and Friday-wear a little less casual.

6. When I was younger I used to wear a lot of T-shirts, but now I wear more and more button-down shirts. I think it’s actually very cool to just have a lot of really great shirts in a very good fabric.

7. It’s important that clothes be light when you’re layering. It’s very nice if you wear three jackets instead of one-but not three suit jackets. I mean a shirt and a shirt jacket and another jacket made out of very light fabric. There’s a richness to that look.

8. A lot of men are very insecure when it comes to dressing. They ask themselves every morning, “What am I going to wear? Is it the right thing? Does it match?” Once they find something they stick to it, and I think that’s a shame. I think men should make a bit more of an effort. They should see clothing not as something necessary but as something fun.

9. here’s something modern about dressing up-wearing a shirt and a tie-but in a lighter way. We made ties that were just strips of fabric–sometimes in the same fabric as the shirt. It’s a new way to wear a tie.

10. I don’t really like wallets. I prefer that you carry your money in your pocket or put everything in a bag and carry it there. Just keep it simple.

1. We’re not living in a very creative era. That’s not good or bad; it’s just the way it is. I think it’s in very bad taste to buy art right now. People should leave it to the hedge-fund owners who want to satisfy their wives. “Hey, I bought a Chinese avant-garde thing.” Good for you.
2. I think it’s very important to look sexy at home. I hate it when people say, “I will take this to the countryside because it’s not fashionable anymore.” I love being well-dressed when nobody’s looking at me.
3. At hotels, they always mess up the cleaning. They will do a crease when it’s not necessary. You give them a cotton shirt and they dry-clean it. It smells funny, so you have to rinse it again. So I travel light.
4. If you can tell a man’s sexuality by the way he dresses—like a “gay” uniform or a “macho” uniform—that’s disgusting.
5. Nowadays, people work out way too much, and they look like invaders from another planet. A guy who works out two hours a day—focusing on his chest because he thinks it’s sexy—you can’t dress him, even if you send him to the best designer or stylist in the world.
6. Finance men have money but no taste. They’ll say, “My wife thinks this tie looks good on me.” They don’t focus on what’s beautiful and what’s not beautiful—they leave it to women.
7. The rock star who uses a personal stylist to dress him should go to jail. If you’re doing rock and roll, you should know how to dress. You shouldn’t need to hire anybody.
8. Anybody can be a good guest for dinner. When it gets delicate is after one day. The worst guests are the people who come to your place and in the morning they say, “Okay, what do we do today?”
9. I once wore a pink, ruffled shirt for dinner, and I wish I had never done it. I thought it was funny, but I felt so bad in it I realized I don’t have the humor to deal with ugliness.
10. After you’re 35, it’s difficult to drink unless you’re running 10 miles a day. I’m not talking one dry martini every Saturday or something. I’m talking three dry martinis a night. And I don’t think that’s possible—it’s too much poisoning. It’s not a very sexy way to talk about drinking, but that’s the truth.

From Details

1. If you’re overdressed, you feel ridiculous. If you’re underdressed, you are ridiculous.

2. The key to being a good host is having an honest interest in the people you invited. You can make an effort without turning the event into a performance and your guests into the audience.

3. The right suit should be comfortable but tailored. It shouldn’t restrict your movements, but it should enhance your figure and give you the silhouette you wish for when you’re undressed.

4. There’s no such thing as a bad style phase, because when you adopt a certain look, you truly believe it’s stylish. In hindsight, the eighties had some awkward moments, but then again, there were some real statements made.

5. Once we were staying at the Ritz in London, and we wanted to have lunch there. We were wearing jeans and no ties. We were refused entrance. So we left the restaurant angry and changed hotels.

6. Men aren’t necessarily dressing up more, but they’re definitely more aware of their grooming. And the first thing that comes to mind in terms of a no-no is a shaped hairline. Or highlights.

7. We don’t recommend that you wear diamonds, but on some men they look good. Sometimes when you have two on it can work. It’s a tricky thing.

8. Some people dress just like their boss. If the boss is a no-tie, blazer, jeans-wearing kind of guy, you’ll see all the people below him dressing just like him. In our case, that’s difficult. We’re kind of schizophrenic. One of us will come in one day in a three-piece suit and then the next day in a baseball cap.

9. We carry our wallets, MP3 players, telephones, and organizers with us every day. We have coats with very large pockets. When we travel, we bring as little luggage as possible.

10. Women are much easier to recognize as style icons—everybody can name a few. For us, male style icons are closer to home: a very well-groomed grandfather or uncle, for instance. The beauty of male fashion is that it is very much quality-based and all about the details: a perfect pair of cuff links or tie bar, a carefully chosen scarf and gloves, a good umbrella.

By Tony Hendra

Want to defend $10,000 DDs (and the women who get them) or burst the silicone bubble? Tell us your position in the comment section.

Boobs are busting out all over. In the year since the Food and Drug Administration approved the use of silicone breast implants (do breasts go under Food or Drugs?), one million shiny new ¼ber-boobs have overflowed welcoming bras like rising dough foaming over bread pans, or strained provocatively against satin blouses and wet T-shirts, pert nipples on red alert. An estimated 500,000 American women have joined the approximately 4.5 million who already had chest extensions, waving good-bye to their S-class-driving nip-and-tuckers with a joyful “Thanks for the mammaries!”

To give you an idea of just how many perky new ¼ber-boobs that is: If you laid them end to end they would stretch from Clifton, New Jersey, to Columbus, Ohio!

We’ve got ourselves an ¼ber-boob explosion!

Actually, ¼ber-boobs can, in theory, explode. Under the right circumstances, lasers can ignite the hydrogen locked up in fresh silicone and it’s boobs away! The CIA is probably picking up the intensified chatter on Al Qaeda sites: Next spring break the bastards aim to infiltrate beaches from Key West to Cancun with undercover Islamo-maniacs carrying handheld lasers. A quick zap where bikini top meets armpit and Great Satan’s milk wagons go kablooey.

Freud famously asked, “What do women want?” He never got around to asking, “Why do women want boobs that feel like Porsche hubcaps?” Before I try to answer that question, a robust caveat: When handling the whole area of boobs, men—even feminist men like myself—tend to be insensitive. We hairy retro-primates assume that the self-sacrifice women endure to enlarge themselves has male pleasure as its only goal. Bigger funbags equals bigger fun, right? Not necessarily. Before we dive headlong into the Valley of Silicone, we must establish whom ¼ber-boobs are intended for.

Consider the harrowing tale of poor little Heidi Montag, who graces the insect-brained MTV series The Hills. The nightmare, the unending torment Heidi had to endure from puberty on, is just agonizing to hear about: She was “too flat.” “Mean boys” would say, “If you nailed two nails in a board, they’d be bigger than you are [hahahahahahahaha!!!].” Can you imagine?

Her courage in escaping that nightmare is as inspiring as it is empowering. She risked death. “Right before I went in, I was like, What if I don’t wake up?” she told US Weekly. Good question. What if? Her struggle is up there with suffragettes being beaten to a bloody pulp as they marched for the vote, or the long battle against brutal male chauvinism waged by Friedan, Steinem, and their sisters. What Heidi went through to get from A to C? MTV ought to spin it off. Call it Heidi’s Hills.

She did it for herself, okay? For her own self-esteem. It had nothing to do with Spencer or the Mean Boys or that slut Lauren (who, incidentally, hasn’t yet gone under the knife and boosted her acne bumps into something worth ogling).

Ogling? Oops. Down, retro-primate, down.

But I wonder. Why would a diaphanous sylph like The Heids saddle her upper half with a couple of humonga-gazongas when she looked just fine in the before shot? Especially since anyone with retinas can deduce that her neo-knockers are mostly liquid sand. How does knowing that others know that boost your self-esteem?

Are they really intended to inspire and empower other women? Hmmm. From what little I know of intimate female discourse, the owners of ¼ber-boobs are assumed to be—how to put this delicately?—morons. The thinking seems to be that even God-given 38Ds were fashioned at the expense of cerebro-cortical mass; wit and tit are inversely proportional.

Is it just possible that ¼ber-boobs are . . . for the lads? Other rumored recipients tend to bear out this wild hypothesis. Take the speculation, based on a flattering photograph that circulated on the Internet, that Ann Coulter had gotten implants. It would make sense, right? If she’s to maintain her role as the reigning Fox News fox, the ultimate eye candy of the loony right, she has to take her job seriously. A cold-blooded Cretaceous reptile must at least look like she can suckle her young.

Or take Posh Beckham, whose ¼ber-boobs, in shape and consistency, closely resemble two halves of a fully inflated soccer ball. Obviously those babies are for Becks, who must like the familiar feel.

Which raises the question: How do they feel? Marriage has limited my ability to conduct large-scale tests, but I do recall that awful moment when you plunge happily into soft pink abundance and come across something like one of those tiny helmets Hell’s Angels wear on their bald spots. Detumescence, thy name is silicone.

As for saline liquid, it’s alarmingly . . . liquid. It sloshes about. Few men—or women—are turned on by #252;ber-boobs that change shape as often as a minor Harry Potter character. Salty ¼ber-boobs do have one thing going for them, though: When you hold them up to your ear, you can hear the sea.

In a sermon several years ago—one he quoted again in October at Larry King’s behest—evangelist Joel Osteen urged the ewes of his flock to shop at Victoria’s Secret. The reason for this apparent lapse from the Christian right’s typical white-lipped terror of sex? Flirty underwear helps wives better please their scripturally mandated lords and masters.

Once you get past the pseudo-feminist claptrap, women who boost their boobs don’t seem a whole lot different from Joel’s ewes. Heidi, et al., are the real boobs, obediently conforming to some caricature of beauty fantasized by traveling-salesman types. Face it, O lovely woman: That shiny new bosom was fashioned by, and for, men. And you will wear it in public as long as men approve. You could say ¼ber-boobs are Western Civ’s equivalent of. . . a burka.

Our buds at Details say the women you date should behave — and look — like grown-ups, not characters from High School Musical.

By Simon Dumenco

Recently, I found myself at a party in Manhattan, casting sidelong glances at a woman. Her look (baby-doll dress, kinderwhore lip gloss) and behavior (exclaiming “Oh my god, totally!” and text-ing obsessively) screamed tweenager. You know, that hybrid archetype—the one who worships at the altar of Hannah Montana and High School Musical. Everything about the woman telegraphed jailbait—except, that is, for the crow’s feet, which suggested that this wannabe tween was pushing 35.

Look around. The 35-going-on-12 woman is everywhere. Man-child Syndrome—the affliction that causes thirty-something guys to cling to adolescence—may be rampant, but lately it’s women who are taking the lead in regressing. Call it the Big Girl Epidemic: women selling versions of themselves that, when you get down to it, are pretty creepy. It’s not so much a Lolita thing—the Big Girl isn’t trying to be a dewy seductress—but more of a daffy, tweenage thing.

Is this the sort of girl you clawed your way into manhood to date? Think back to what your big brother’s girlfriend seemed like when you were a kid: A woman. A w-o-m-a-n woman. Not someone who speaks in acronyms and carries a glitter-covered Sidekick.

“I get the feeling that a lot of women are dressing and acting that way because they think that that’s what guys want,” says Jean Twenge, associate professor of psychology at San Diego State University and author of Generation Me, a book about American youth culture. “It’s the same thing as older women getting plastic surgery. The idea is that what men want is a woman who looks 18. Although they don’t usually want a woman who acts 18.” Twenge laughs, then adds, “And that’s where the problem comes in.”

And it is a problem—especially if you’re a man who happens to find tween impersonations not only unbecoming but more than a little sad. Unfortunately, as long as our culture reinforces the Big Girl’s worst inclinations, the epidemic will persist.

“I’ve been meditating on the question of why women in their twenties and thirties seem to be obsessed with all things teen—fashion, slang, gossip, et cetera,” says Anastasia Goodstein, publisher of ypulse.com, a marketing website. “The reality is that teen culture has come to define pop culture.” As the usual markers of American adulthood—marriage, career, kids—get more and more delayed, the simpleminded distractions of adolescence have extended their grip on the adult brain. Man-children may drag their old skateboards and video games with them into their thirties, but Big Girls needn’t bother to cling to the pop culture of their youth. “Adult” pop culture has been conveniently colonized by a teen sensibility. Consider Gossip Girls or The Hills. Both shows are endlessly blogged about and compulsively parsed by teenage girls—but they’re also cornerstones of thirtysomething women’s party conversation. The audiences have converged.

Meanwhile, the female-oriented tabloids—Us Weekly, In Touch, and Star—read like Tiger Beat redux, chronicling the dysfunction of the Lindsays, Britneys, Nicoles, Heidis, and Laurens who have come to dominate the celebrity landscape at the expense of more seasoned female celebrities. And you only need look at the teen/tween style bible Teen Vogue to discover where Big Girls are taking their fashion cues from. According to the demographic stats it supplies to advertisers, nearly 2.8 million readers (almost half the total) of Vogue’s little sister are adults.

Dating one of these Big Girls doesn’t mean just putting up with jailbait fashion and IMs that say OMG, totally! It means potentially enduring the worst sort of navel-gazing drama. As Twenge points out, arrested development goes hand in hand with self-absorption: Narcissism “is a very adolescent personality trait. Obviously it means you focus on yourself and what’s good for you.” It used to be that men had the ego market cornered, but now, Twenge says, “there’s virtually no difference between the sexes with regard to narcissism. Most of the change has taken place in girls and women.” Basically, women have caught up to men by sinking to comparable levels of adolescent self-absorption.

Which makes the idea of actually dating a Big Girl even more unappealing.

Not that, in this postfeminist age, you have to hold out for “I am woman, hear me roar.” But “I am girl, hear me giggle”? Uh, no. Totes no.

How a pack of skinny girls became better tabloid fodder than any young actor. PLUS: Play “Spot the Bad Boy” and pick out the real renegades—then share your take on the candyass leading men of today.

-Bart Blasengame

Approximately 144 consecutive hours into CNN’s coverage of Paris Hilton‘s release from jail, my vision got a little blurry. A hot tear balled up in my left eye and I began imagining Paris Hilton with a penis. Yes, a penis. A nice, healthy man-appendage swaddled in Levi’s. I even added some facial shrubbery to her cheeks.

Because while having Hilton & Co. suddenly flood the police blotters increases our chances for a show called Simple Life: Caged Heat, it also raises an unsettling question: When did the Hollywood Bad Boy become a Hollywood Bad Girl?

Renegade lovelies like Lindsay Lohan, Britney Spears, and Paris Hilton are staging their own real-life, white-girl version of Set It Off: They’re doing things like sucking down spliffs while cruising L.A. boulevards, playing smash-up derby in their convertible Benzes, snorting rails at VIP clubs, and flashing their labia like an American Express Black card. Apparently, their male counterparts are too busy getting their eyebrows sculpted and perfecting their pigeon poses to join them.

“They’re all a bunch of marshmallows,” says James Parish, author of Hollywood Bad Boys: Loud, Fast and Out of Control, of young male celebrities. “Older men like Mel Gibson and Russell Crowe are still belligerent, but as for the new breed of actors, Elijah Wood isn’t exactly Johnny Depp.” Frankly, Jim, he’s not even Scott Baio. And neither are any of the other Eagle Scouts pounding green tea on the back patio of the Marmont. They’re either too busy prioritizing the environment over model nookie (Leo), making babies with mere mortals (Tobey), treating the 12 steps like something other than a speed bump (Joaquin), or grinning like a simpleton amid the sickening stagnation of a committed relationship (Matt, Ben, Heath).

Since as far back as the twenties, self-destructive thespians have been a fixture in Hollywood. Fatty Arbuckle allegedly raped and murdered a girl—and got off scot-free (though the scandal did put an end to his career). After Fatty came unapologetic embodiments of trouble like Robert Mitchum, Frank Sinatra, Marlon Brando, and, of course, Steve McQueen, a drug-devouring, chopper-straddling, womanizing, gun-toting Republican. In the eighties, Rob Lowe filmed himself having sex with two girls in an Atlanta hotel room—one of whom was 16. Not bad. But somewhere between Sean Penn’s last frothing swing at a cameraman and Robert Downey Jr.’s famous Palm Springs cocaine bust, we’ve lost our way.

“Yeah,” actor Corey Haim says with a weary exhale. “They’ve all gone soft. Now Robert’s into yoga, meditation, and natural herbs.” Haim, the cuter half of the pair of Coreys who ruled teen cinema in the late eighties, knows all about what it means to be a Hollywood Bad Boy.

“I was 17 and doing stuff crazier than anybody out there today,” says Haim, who’s getting a second shot at infamy with an A&E reality show costarring Corey Feldman called The Two Coreys. By his mid-twenties, Haim had been in and out of rehab several times and had filed for bankruptcy once: “When you have that sort of money and access at that age, it’s kind of expected.”

Kind of?! Hell, it’s obligatory. When Colin Farrell, our best hope for an Errol Flynn-style return to decadence, completes a stint in rehab and then fights to keep a tape of himself having sex with a Playboy Playmate out of our hands, something isn’t right. But until Shia LaBeouf starts banging the lead grinder at the Crazy Horse, or Frankie Muniz is popped with a kilo of Mexican brown up his ass, we’re left with two options: Suffer through the faux tantrums of rich kids like Sean Stewart and Brody Jenner while we wait for a bona fide savior to lift us from our mama’s-boy-induced malaise, or gape in awe at the Cat Pack: Blo-han, Brit-Brit, and Inmate No. 9818783 tearing through velvet ropes with a squad of cop cars in hot pursuit.

“Hey,” Haim says with a growling smoker’s chuckle, “at least they look good doing it.”

Come back, Corey. Hollywood needs you.