If your thirtieth birthday is in your rearview, lose the rebellious-teen uniform.

-By Katherine Wheelock

Still clinging to that earring and biker jacket? Tell us your thoughts on dressing younger than your years right here.

Image credit: infgoff.com

Call up a mental picture, for a moment, of Dina Lohan. In your mind's eye, the 45-year-old stage mom is probably wearing a low-cut top and a denim miniskirt. Maybe a pair of UGGs. In other words, an outfit a lot like one her 21-year-old daughter would wear. If you're reading this story and you're a 35-plus-year-old wearing a faux-vintage Urban Outfitters T-shirt and plaid Vans, you and Dina Lohan have a lot in common. Only, not having a honey-colored spray-on tan and highlights, you don't look as good.

An unusual wash is one thing. Denim embroidered like a throw pillow is another.

-By Katherine Wheelock

How do you take your denim? Defend bedazzled jeans—or stand up for basic blues—in the comment section below.

Image credit: NINA PROMMER-GLOBE PHOTOS

The torn knees, the bleached thighs, even the girlishly embroidered back pockets—those could have been predicted. But no one saw this coming: At the Country Music Awards a few years ago, the person in the most jaw-droppingly ornamented denim outfit—the country-western equivalent of Louis XIV's brocaded finest—wasn't Dolly Parton, it was Keith Urban. Granted, it was the Country Music Awards, where the red carpet isn't exactly a parade of Jil Sander minimalism, but Urban's clingy jeans, covered with doily-like embroidery, represented a tipping point.

An invitation to a black-tie event isn't a license to bastardize the penguin suit.

-By Katherine Wheelock

Speak out in favor of the red-tie-with-tux look—or trash alternative black tie altogether—in the comment section below.

Image credit: WireImage.com

Black tie should be one of the sweetest phrases a man can hear. It means you won't have to think about anything when you get dressed that night. You won't have to fuss over whether you should go tie or no-tie, or bicker with anyone about whether you can get away with jeans. You'll wear a tuxedo—which, if you've graduated from a backpack to anything made out of leather, you probably own. But for some guys—most conspicuously, celebrities—the words black tie have become a cue to rouse their inner George Clinton.

Unless you're Tom Ford, a splayed shirt makes you look like a game-show host.

-By Katherine Wheelock

Think using your collar to pay homage to Elvis is respectable? Say your piece in the comment section.

Image: Everett Collection

Nick Lachey's is pretty much permanently out. Tony Parker's is too. Ryan Seacrest's makes regular external appearances—usually on formal occasions. And lately Entourage stars Kevin Connolly's and Adrien Grenier's are not only out but spread so wide that looking at a snapshot of them could put "Stayin' Alive" on a loop in your head for days. The Big Man Collar—a phenomenon that once seemed safely trapped in the amber of the seventies—has somehow returned full-force.

If you're old enough to drive, you shouldn't be asking your stylist for bangs.

-By Katherine Wheelock

Take a cut at the boyish hairdo below.

Image credit: Photofest

Taking the occasional style cue from guys a decade younger than you isn't the worst idea. It keeps you a safe distance from the threshold of grandpa-dom. Laceless All Stars. Denim jackets. Rugby shirts. A man over 30 can get away with these youthful accents from time to time. What a man over 30—a man over 20—cannot get away with is the most recent trend to emerge from the hallways of American adolescence: side-swept bangs. Zac Efron, 20, the pearly-toothed, sapphire-eyed star of the Disney Channel's High School Musical, is the poster child for the cut. But men like 28-year-old Fall Out Boy Pete Wentz are propagating it too.

Even if your undergrad regalia still fits—barely—you shouldn't be wearing it out.

-By Katherine Wheelock
-Photograph by Christian Patterson

Want to trash or defend worn-in Yalie gear? Here's your chance. Say your piece in the comment section below.

Photograph by Christian Patterson

Take your college yearbook down from the shelf. Thumb through to a picture of yourself—maybe the one of you in an alma mater-issued lacrosse shirt, arms slung around your classmates' shoulders. Do you think you dressed better then? Do you think you looked more employable—more bankable? Unless you were an undergraduate version of Alex P. Keaton, that's doubtful. You probably looked like a keg-standing tyro. And that's okay—you were a keg-standing tyro. What's not okay is dragging that look into your adulthood like a well-worn blankie.

Your denim should look like it belongs to Paul Newman, not Matt Lauer. PLUS: Watch our video of other unforgivable fashion missteps that come with fatherhood.

-By Katherine Wheelock

Do you think dad denims have a place in a father's life, or should they be banished along with "WORLD'S BEST DAD" T-shirts? Make your case here.

Photo: Lawrence Schwartzwald/Splash News

It wasn't a good day for Matt Lauer. We're not talking about the day Tom Cruise verbally bitch-slapped him on national television (You should be more responsible), or the day he had to be the one on the bottom in a doubles-luge stunt with Al Roker. We're talking about the day a photo of him at a Gucci party in the Hamptons showed up on the media-gossip site Gawker.

Lauer—locked in a side hug with Jessica Seinfeld, head thrown back in a hearty laugh—was wearing what can only be described as dad jeans: the male version of the snug, extra-high-cut denim slacks Rachel Dratch immortalized in the Saturday Night Live commercial for "Mom Jeans" a few years ago. The wash? Wal-Mart blue. The crotch? The length of a baby's arm.

Click here for the fatherhood fashion video

Unless you just finished water-skiing, there's no excuse for wearing Croakies. Think Bollés and Brooks Brothers are a winning combination? Sound off here.

-By Katherine Wheelock
-Photograph by Idris Rheubottom and Tony Craig

Athletic signifiers have a rightful place in men's wardrobes. Diver's watches appropriate for Navy seals can be worn with gossamer cashmere sweaters; basketball shoes have become legitimate accompaniments for tailored pants. But there is a line past which pro-athlete style can no longer commingle with office and cocktail attire. That line is embodied in a pair of Iridium-lensed Oakleys slung around the neck of a Wall Street banker.

What makes you think a loud shirt that's inappropriate by day will look cool unbottoned after hours? Plus: Watch the video escapades of real-life fashion offenders; and sound off about this troubling style trend in the comment section.
-By Katherine Wheelock

Photos: WireImage.com (10), INF (2), Photofest (1), Corbis (1), Getty (1)

No doubt you've earned a night out. All week you rose at a painfully early hour, dutifully tied a four-in-hand, and headed off to an airless office. You deserve to let loose. There's a cocktail for that. There is not, contrary to what guys streaming into velvet-roped clubs on Saturday nights seem to think, a shirt for that.

"You can tell it's the shirt the guy saves for the weekends," designer John Bartlett says. "You get the feeling it has hair gel stains on it from the last time he went out."

You can spot this article of clothing through whiskey goggles from 50 yards away. It's a button-down shirt, usually untucked and always in a print—multicolored stripes, paisley, florals—or a solid color with a slight sheen. If it could speak, the Go-Out Shirt would say what the man wearing it is burning to blurt out—"Yes, I sell mutual funds for a living, but I'm a really fun guy!"