10 Best Dressed

updated 09/28/2009 AT 01:00 AM EDT

originally published 09/28/2009 AT 01:00 AM EDT

Kate Winslet

Best Red Carpet

The royal blue Narciso Rodriguez gown with Chopard diamond drop earrings (in L.A. in January) looks regal.

Major sparkle—on the Balmain dress and the bling—highlights basic black (in L.A. in December).

The star goes classic Hollywood glam in Atelier Yves St. Laurent (in L.A. in February).

Winslet flaunts her curves—and tan!—in Hervé Léger (in N.Y.C. in December).

Get Kate's Look!

WET SEAL Zip-front bandage dress, $30.50; wetseal.com

ALDO Embossed clutch, $30; aldoshoes.com

KENNETH COLE "Hey Stud" pumps, $90.72; endless.com

How She Does It

"Kate dresses to really show off her curves," says stylist Freddie Leiba, who has worked with the star. "She doesn't like bubblegum colors." So by choosing dark shades with the occasional pop of color and pairing "simple silhouettes" with "classic diamonds," she epitomizes timeless beauty.

Reese Witherspoon

Best Short Dresses

The bold color of this Temperley London dress (in San Francisco in May) contrasts with the ladylike shape.

The Rodarte dress (with Balenciaga heels in L.A. in March) is all about pattern.

Black Fendi looks anything but basic with a tiered skirt and sexy neckline (in L.A. in January).

Get Reese's Look!

JESSICA MCCLINTOCK Little black dress, $111; jessicamcclintock.com

NINE WEST "Janalynn" satin dress pumps, $79; ninewest.com

How She Does It

In 2009 "we got a Reese we haven't seen yet," her hairstylist Mark Townsend told PEOPLE. Stepping out in edgy patterns, bold colors and hemlines perfect for her petite frame, the star, 33, perfected a look that is "confident and modern."

Michelle Obama

Best Accessible Glamour

Obama (in Moscow in July) has gotten use out of this Jason Wu dress, wearing it for multiple appearances.

Yes, you can find a First Lady wardrobe at the mall! Her J. Crew look (in London in March) includes an $18 tank top.

Obama (in Jason Wu in Rome in July) often champions up-and-coming designers like Wu and Thakoon.

Get Michelle's Look!

WHITE HOUSE BLACK MARKET Mesh Flower Pin, $25; whitehouse blackmarket.com

J. CREW Ink Dot dress, $148; jcrew.com

BCBGENERATION "Ariel" peep-toe pumps, $69.90; endless.com

How She Does It

"I don't consider myself a fashionista," Michelle Obama, 45, told PEOPLE. Many would beg to differ. She made sleeveless sheaths must-haves—the better to show off those rocking arms—and wears J. Crew and couture with equal grace.

Taylor Swift

Best Sparkle

Simple accessories and makeup tone down a flashy Collette Dinnigan dress (in L.A. last November).

Swift's sparkly Kaufman Franco gown (in Nashville last November) "was so heavy but totally worth it," she says.

This Naeem Khan (in L.A. in April) has a modest hemline: "I'm tall, so I can't wear a skirt that's too short."

Get Taylor's Look!

SCALA Black strapless sequined dress, $138; edressme.com

FOREVER 21 Expandable teardrop cuff, $14.80; forever21.com

PARIS HILTON "Destiny" pumps, $89; macys.com

How She Does It

"Anything that glitters hypnotizes me," says Swift, 19, of her red-carpet signature style. "It's always an attention grabber." Adds stylist Joseph Cassell, who keeps her accessories simple: "She does sparkle in a grown-up way."

Beyoncé

Best Street Chic

The star's perfect hair and makeup jazz up a basic white tank and jeans (in Berlin in May).

Beyoncé accessorizes her shopping outfit with a statement necklace (in Paris in May).

A glittery belt is the focal point of the outfit she wore while out and about in Chicago in July.

Get Beyoncé's Look!

EXPRESS White burnout tee, $24.50; express.com

7 FOR ALL MANKIND Straight leg jeans, $175; Retail stores nationwide

R2 "Sonoma" sandals, $55; piperlime.com

How She Does It

You'll rarely see her in sweats. "Even when she's dressing down, she will accessorize with items that make the outfit pop or wear her hair in a glamorous style," says the 28-year-old star's longtime hairstylist Kim Kimble.

Vanessa Hudgens

Best Hippie Chic

Loose waves pair perfectly with Hudgens's floral Rebecca Taylor dress (in L.A. in March).

Dramatic ruffled sleeves elevate a white Temperley London dress (in N.Y.C. in August).

Black gladiators (and polish!) add edginess to a flirty Gold Hawk dress (in L.A in April).

Get Vanessa's Look!

JANIQUE Short aqua cocktail dress, $338; edressme.com 20% discount for People readers. Enter "people" at checkout.

FOREVER 21 Filigree pendant necklace, $6.80; forever21.com

MARCIANO "Carolina" strappy platforms, $187.96; endless.com

How She Does It

"Vanessa's style goes from sweet hippie girl to rocker chic," says stylist Deborah Waknin of the 20-year-old star's blend of "feminine and easy" pieces that are "non-matchy." Hudgens's mantra? "Not trying too hard."

Cameron Diaz

Best Jeans

Pink lips and red heels liven up jeans and a white shirt (in L.A. last October).

Ripped 7 For All Mankind jeans look polished with a Michael Kors top and Dsquared2 shoes (in L.A. in March).

Pierre Hardy heels add edge to Diaz's J Brand jeans and Lela Rose top (in N.Y.C. in June).

Get Cameron's Look!

EXPRESS Buckle cuff shirt, $49.50; express.com

EXPRESS "Stella" skinny leg jeans, $59.50; express.com

JESSICA SIMPSON COLLECTION "Amona" shoes in Cherry, $89; jessicasimpsoncollection.com

How She Does It

"Cameron is the ultimate denim girl—it's what she feels the most herself in," says stylist Rachel Zoe. To add polish, Diaz, 37, "always uses a dash of color or a modern shoe that pulls the look together effortlessly."

Freida Pinto

Best Use of Color

The yellow Christian Lacroix gown she wore in L.A. in January "enhanced her golden complexion," says Paul.

Diamonds add flash to the star's cornflower blue Marchesa dress (in L.A. in January).

Studded shoes are an unexpected pairing for Pinto's Dries Van Noten dress (in London in February).

Get Freida's Look!

FOREVER 21 Belted linen dress, $22.80; forever21.com

STEVE MADDEN "Kerrin" shoes, $100; jildorshoes.com

How She Does It

"She is not afraid of wearing clothes that have vibrant tones or rich colors," says Pinto's makeup artist Jeffrey Paul. The 24-year-old star's go-to shades? "She is stunning in pinks, blues and yellows," says her stylist George Kotsiopoulos.

Nicole Richie

Best Maternity

Richie gives basic black a boho vibe (in Nicole for A Pea in the Pod in L.A. in August).

The star demonstrates her love of maxidresses (in Issa in Miami in May).

Richie pairs exotic accessories with a bold red Issa dress (in L.A. in February).

Get Nicole's Look!

BANANA REPUBLIC Modern locket necklace, $48; bananarepublic.com

NICOLE FOR A PEA IN THE POD Kimono blouse, $78; 877-273-2763 for stores

NICOLE FOR A PEA IN THE POD Tank minidress, $68; 877-273-2763 for stores

MICHAEL ANTONIO "Sisley" sandals, $54.95; endless.com

How She Does It

"The last thing a pregnant woman wants is to feel like she's wearing maternity clothes," says Richie, 28, who designed and launched her own clothing line with A Pea in the Pod in August. "I love prints and maxidresses."

Kim Kardashian

Best Bikinis

Kardashian (in Malibu in July) adds a sarong to her Anika Brazil bikini.

Bold colors (like in this L Space bikini) "draw the eye away from your flaws," says the star.

Accessorizing with jewelry "adds fun" to her L Space bikini, says Kardashian.

Get Kim's Look!

CALAMITY JANE Statement necklace, $24; shopthelook.net

CIA MARITIMA Triangle top ($45) and tie-side bottom ($50); ciamaritimaus.com

How She Does It

"It's about trial and error," says Kardashian, who favors boldly colored suits with tie bottoms for adjusting and triangle tops for support. And the reality star, 28, isn't afraid to accessorize: "A sarong is my No. 1."

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