Stars' Fall Date-Night Style

01 of 15

TAILGATE

She shoots, she scores! wins major points with beau by sporting a matching hockey jersey while cheering on the Winnipeg Jets.

02 of 15

THEATER NIGHT

CLOSE ENCOUNTER — Eric Charbonneau/WireImage

Catching a new play? Poke holes in the LBD like the queen of casual-cool , who grabs coordinated evening accessories like an oversize clutch – and her dressed-to-impress boyfriend Justin Theroux! – at the American Cinematheque Award event in L.A.

03 of 15

SOCIAL STYLE GATHERING

Sexy? Check! Chic? Check! Boasting a sizzling hemline in an of-the-moment bright, spicy long-sleeve shift does double duty, dazzling husband and stylish friends alike at Louis Vuitton’s Paris fashion week show.

04 of 15

CONCERT

Groove along to your favorite band in a flirty top and sexy leather leggings like , who dashes out in N.Y.C. in platform pumps that provide extra comfort for dancing with BF Scott Disick. But be sure to throw a pair of flats in your bag just in case!

05 of 15

CHARITY BALL

Garnering a kiss from husband Josh Kelley at the Elle Women in Hollywood Awards, provides the perfect amount of shine to spotlight a good cause with her embellished frock, glittering clutch and satin slingbacks.

06 of 15

BLACK-TIE WEDDING

As temperatures dip and weddings start moving inside, the occasion gets much more formal. Snag and low-key styles (she’s in a Vivienne Westwood gown and Louis Vuitton clutch at the Toronto International Film Festival premiere of his flick Moneyball) to look effortlessly elegant and always appropriate.

07 of 15

ART GALLERY OPENING

and her new beau Justin Theroux are making the most of their N.Y.C. residence, wearing chic outfits to hit the town.

08 of 15

DINNER WITH FRIENDS

and her fiancé Eric Johnson wear flirty his-and-hers denim looks – a Love Sam top and cutoffs for her, plaid button-down for him – to hit Beverly Hills’s Mastro Steakhouse with pals.

09 of 15

COCKTAIL PARTY

Hollywood’s hottest new duo, and Stacy Keibler, show off their new romance in style, with a sexy suit and elaborately ruffled halter for a night out at the Toronto International Film Festival.

10 of 15

AMUSEMENT PARK

Another hot new couple, and indulge their inner kids by spending a casual day at Disneyland’s California Adventure Park in Anaheim, Calif. – carrying layers in case it gets chilly for the evening’s fireworks.

11 of 15

SPORTING EVENT

Take a cue from and Jay-Z, who hit the U.S. Open in N.Y.C.: When dressing for sporting events this season, comfort is key. Still, you can add a little sparkle – and a great hat will keep the sun out of your eyes and your focus on the field.

12 of 15

ZOO DATE

and extend their PDA to include matching outfits – choosing sky-blue polos and comfy kicks to stroll the L.A. Zoo.

13 of 15

HITTING THE BAR

Newlyweds and Kris Humphries hit an N.Y.C. bar to watch a little football, picking outfits that can easily transition from day to night if they are having too much fun to head home.

14 of 15

DINNER AND A MOVIE

As new parents, and Cash Warren make a point to carve out time together, even getting a little fancy for a laid-back evening in a sleek white blazer and patent clogs.

15 of 15

BEACH DATE

Got a fun trip planned for an upcoming long weekend? Don’t just toss on an old tee as a cover up – make like Molly Sims on her Hawaiian honeymoon with Scott Stuber and tie a sexy scarf (hers is Theodora & Callum) around your waist for an eye-catching coverup.