By People Staff
November 15, 1999 12:00 PM

At various times during his boyhood, Virginia-born actor Diedrich Bader owned a necklace made from machine-gun bullets, wore nothing but thrift-store clothes and was content to get his hair cut only once a year. “And I’d never brush it,” he adds, “so I’d get these big matted clumps of rattiness.”

The 6’2″ Bader, 32, has learned from his mistakes—although you wouldn’t know it from the character he plays, package delivery guy Oswald Lee Harvey on ABC’s The Drew Carey Show. In real life, Bader, who lives in Los Angeles with his wife, actress Dulcy Rogers, now favors clothes that have “a casual elegance” like “a button-down shirt, some jeans and nice shoes.”

The good news is that any man can make such a transition—or so say the fashion and grooming experts whom we asked to fill us in on today’s sexiest male looks. The bad news? As Miami stylist Danny Santiago puts it: “Men are afraid to experiment; they’re scared to take chances.” Los Angeles stylist Cary Fetman agrees. “Men always think the safest thing is the best thing,” he says.

But there has never been a better time to make a change. “Men are now being given the same opportunities as women,” says celebrity hairstylist José Eber. So we asked a team of pros from around the country—which also included L.A. stylists Eric Berg, Kim Bowen and Jo Goodman; Terry Maki of Washington, D.C.’s RPM Hair and Skin Care Center; New York City stylist Rachel Zoe Rosenzweig and Tom Julian, a trend analyst for Fallon McElligott ad agency—for tips to make over any guy. As Bader recently discovered when he bought a three-button, dark blue Hugo Boss suit, there’s nothing a woman finds sexier than a well-dressed man. “It’s my lucky suit,” he quips. “When I put it on, it’s lucky my wife and I make it out for the evening!”

Knit shirt

Tops should be fitted but not skintight. “One of the biggest mistakes men make,” notes stylist Rachel Zoe Rosenzweig, “is that they wear their clothes too big.”

Flat-front pnants

“Right now, the silhouette is looser, with wider legs,” says trend analyst Tom Julian.

Monochromatic outfit

Stylist Danny Santiago says the tone-on-tone look is “modern and simple and very clean.”

Round-toe oxfords

Shoes should not be “overly detailed,” Danny Santiago says.

Naturally styled hair

“You should follow the flow of the hairline,” says hair and makeup expert Terry Maki.


This neckline flatters anyone, “except guys with really hairy chests,” stylist Jo Goodman says.

Slicked-back hair

“Over-gelled hair is frightening!” declares stylist Kim Bowen. How do you know you’re using too many styling products? “A girl shouldn’t be afraid to run her fingers through it,” says stylist Danny Santiago.


“It’s passé—and way too Hollywood,” says stylist Jo Goodman.

Heavy gold chains

Says stylist Cary Fetman: “We’re not back into Vinnie Barbarino.”

Too much chest

“If someone thinks for a millisecond that you stood in front of a mirror buttoning and unbuttoning, it’s a terrible thing,” says Kim Bowen.

Floral-print silk shirt

“Yuck, no!” groans stylist Eric Berg, who derides this as “the laid-back Palm Springs look.”

What’s HOT

Oxford-cloth shirt

The button rule: “Never show more [skin] than below the collarbone,” says stylist Rachel Zoe Rosenzweig.

Leather jacket

Trend analyst Tom Julian claims that “leather is probably the most good-looking item a man can own.”

Silver-buckle belt

“You want a nice, simple belt that isn’t super-wide,” says stylist Danny Santiago.

Well-fitting jeans

“You’ve got to have a good pair,” insists stylist Eric Berg. That means not too relaxed—but not too tight.

Ankle boots

“One of the sexiest things on a guy,” says Rachel Zoe Rosenzweig.

What’s Always Sexy

  • A leather jacket
  • A cashmere turtleneck
  • A fitted, white cotton T-shirt
  • A good pair of jeans
  • A button-down shirt—with no more than the top two buttons undone
  • Clear skin
  • A classic tuxedo
  • Well-groomed facial hair (likeBen Affleck‘s, below)

What’s NOT

Basebal cap

“Not unless you’re going to the gym,” declares stylist Eric Berg.

Nose lings et al

“Inducing pain on yourself is never attractive,” says stylist Rachel Zoe Rosenzweig.

Body art

“There are very few people covered with tattoos who look good,” stylist Kim Bowen says.

Hip-hop style

“This look is kind of over,” stylist Danny Santiago observes. “There’s something deeply foolish about grown men with their buttocks jutting out over the top of their trousers,” adds Kim Bowen.


“Not unless you’re doing a sport,” says Rachel Zoe Rosenzweig.

What’s Never Sexy

  • A comb-over
  • A light suit with a black T-shirt
  • Capri pants
  • Overpowering cologne
  • Thong bathing suits
  • Nylon socks
  • Wearing one designer label head-to-toe
  • Fur
  • Banded collars
  • Sneakers with dress pants
  • Garish tattoos
  • ”Creative black tie” (like Don King’s attire, below)

What’s HOT

Suede bomber jacket

“The brown is very friendly,” says stylist Jo Goodman. “It’s sort of a guy-next-door look.”

Silver jewelry

“It should be kept simple, not showy,” stylist Danny Santiago says.


Fashionable females tell the opposite sex how to dress for success

Camryn Manheim

“I really love bold choices, people who break the rules. I like guys who aren’t following trends but setting them.”

Dyan Cannon

“I don’t like real tight jeans on men; I love sweaters with collared shirts underneath.”

Helena Bonham Carter

“Cologne or aftershave is very important.”

Bridget Fonda

“I like a good suit. I’ve been spoiled by all these film images of Gary Cooper and Cary Grant!”

Gloria Reuben

“I love men in cotton boxers.”

Sheryl Lee Ralph: “A well-cut, good-fitting black shirt with a white T-shirt underneath just son of rocks my boat.”

Gena Lee Nolin

“I love a guy in a suit—someone who puts on his nice Armani pants.”

Julianne Moore “Bad hygiene is never sexy.”

Alex Kingston

“If a guy has really good pecs and wears a tight T-shirt, that’s really sexy.”

Molly Shannon

“I like white shirts with a V-neck blue sweater over them. And I like cargo pants.”

Rose McGowan

“A guy in a gray cashmere turtle-neck always does it.”

Christine Baranski

“I like the cowboy look: leather jacket, motorcycle and fedora—it’s Harrison Ford in Indiana Jones.”

Lisa Ling

“I don’t think sexy means showing a lot of skin. To me sexy is actually stuff that has yet to be revealed.”

Rosie Perez

“I love a three-quarter length leather jacket.”

Jane Seymour

“I hate baggy pants, because I don’t like seeing guys’ underwear unless they’re taking off their clothes! But I love blue shirts—they do amazing things for men’s eyes.”

What’s Sexy for the Next 15 Min.

  • Ricky Martin-style highlights (left)
  • Sideburns
  • A four-button tuxedo
  • Solid-color ties
  • Bucket caps
  • An earring in each ear Shiny, futuristic-looking outerwear
  • Black leather pants—Cargo pants (left)
  • Silver jewelry
  • Bead bracelets
  • Nylon running pants
  • Stretch clothing

What Was Over 15 Min. Ago

  • Yellow- or blue-tinted sunglasses
  • Baseball caps—especially when worn backwards
  • Wraparound eyeglasses
  • Over-gelled hair
  • Visible underwear
  • Sweatpants
  • Body piercing
  • Cuffed jeans
  • Pleated pants
  • The Mr. Muscles look (a la Jean-Claude Van Damme in 1998, below)