A Cool Girl's Guide To Nighttime Dressing

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    Falling somewhere in the middle of the evening style spectrum poses some challenges, particularly in cold temperatures, so we’ve turned to our favorite stylish ladies like Kate Bosworth, Alexa Chung, Cara Delevingne and more, for inspiration.

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    Kate Bosworth

    Once the temperature starts to rise, opt for a coordinated skirt set in a sheer fabric for a modern twist on ladylike style.

    At the Van Cleef and Arpels South Coast Plaza Boutique Celebration in California, Bosworth is wearing a Monique Lhuillier S/S 14 Dress, Van Cleef and Arpels Jewelry, and an Edie Parker Lara Clutch ($995).

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    PHOTO: Neil P. Mockford/FilmMagic

    Cara Delevingne

    No evening outfit list is complete without the trusty little black dress. Achieve Delevingne’s relaxed look by wearing yours under a long, boyfriend coat and throwing your hair into a messy bun.

    Attending her sister’s wedding lunch, Delevingne wore a Burberry Prorsum Tailored Cashmere Coat ($3595) and Open Back Jersey Dress ($1995).

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    Ann Demeulemeester

    Deconstructed Slip Dress ($269) in Black

    ‚ÄčTopshop Wool Boyfriend Coat ($196) in Bright Orange 

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    PHOTO: Vantagenews/AKM-GSI

    Kate Moss

    Steal Moss’ style by pairing a statement pendant and metallic clutch with your black and gray basics.

    On a recent night out in London, Moss carried Stella McCartney Falabella Chamois Fold Over Clutch ($925).

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    Dree Hemingway

    A simple black top and white crepe trousers look effortless when paired with loose waves and a fun clutch.

    At the 2014 amfAR New York Gala, Hemingway wore a Chloe Taffeta-Trimmed Crepe Top ($2995) and Stretch Wool-Blend Tapered Pants ($950).

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    Phillip Lim Textured Cropped Trousers ($395)

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    PHOTO: Neilson Barnard/Getty Images for Target

    Alexa Chung

    Dress down a fun, printed mini with a louche sweater, opaque tights, and a block heel.

    Celebrating the Peter Pilotto for Target Launch in New York, Chung wore a Peter Pilotto for Target Skirt ($35).

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    Peter Pilotto for Target Skirt ($35)

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    Jourdan Dunn

    A floor-length metallic slip dress doesn’t have to be relegated to the red carpet. Instead add ankle boots, a v-neck sweater, and top with a leather biker jacket.

    Leaving the Jason Wu F/W 14 fashion show, Dunn wore Valentino’s Studded Leather Biker Boots ($1495) and carrieda Stella McCartney Falabella Denim Fold Over Tote ($1195).

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    Nili Lotan Maxi Cami Dress ($495)

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    PHOTO: JB Lacroix/WireImage

    Arizona Muse

    Girly dresses not your thing? Try a tailored black suit with a casual white tee underneath.

    At the Warner Music Group's Grammys after-party, Muse wore a Balmain Blazer and Pants (no longer available) with a Valentino Rockstud Flap Leather Shoulder Bag ($2745).

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    PHOTO: David M. Benett/Getty Images

    Suki Waterhouse

    A long-sleeved jumpsuit in a dark floral print looks great with brown accessories and a cardigan jacket.

    At the RoboCop premiere after-party in London, Waterhouse wore a Reformation Cairo Jumper ($258).

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    Cairo Jumper ($258) in Black Floral

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    PHOTO: Mireya Acierto/Getty Images

    Olivia Palermo

    Instead of a tank top, wear a printed silk blouse, fluffy v-neck sweater, and finish with a faux fur scarf.

    Arriving at the Peter Som F/W 14 fashion show, Palermo is wearing a Tibi Two-Tone Crossover-Front Jumpsuit ($333); Fendi Fur-Trimmed Calf-Hair Shoe Boots ($1790).

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    Luncheon Shirt ($62) in Pink

    Barneys New York Faux Fur Crossover Scarf ($50) in Black 

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    Jessica Alba

    Juxtapose a printed sweatshirt with a leather pencil skirt for a warm and fun evening look.

    At the Beverly Hills Chamber of Commerce EXPERIENCE event, Alba wore a Kenzo Tiger Print Sweatshirt ($269) and Nine West Women’s Cashy Ankle Boots ($129) with a Valentino Rockstud Clutch ($1845).

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    Clover Canyon

    Gold Panther Printed Neoprene Sweatshirt ($246) in Multi

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    PHOTO: Dara Kushner/INFphoto.com

    Karlie Kloss

    Up the ante of your all-black ensemble by adding sleek, pointed pumps and a leather bomber jacket.

    Leaving the Jason Wu F/W 14 fashion show, Kloss wore a Coach Leather Varsity Jacket ($1098).

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    Club Monaco

    Gabi Varsity Jacket ($398) in Rum Raisin

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    PHOTO: David M. Benett/Getty Images for InStyle

    Anna Friel

    Jumpsuits are the cool girls’ answer to cocktail attire; try a structured strapless version with heels or ankle boots.

    At a pre-BAFTA party held by InStyle UK, Friel wore a S/S 13 Osman Strapless Embroidered Jumpsuit.

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    Rachel Roy

    Strapless Jumpsuit ($69) in Navy

Shop this Story
Essential Straight-Cut Blazer and Trouser

Essential Straight-Cut Blazer and Trouser

Mango, $170
Deconstructed Slip Dress

Deconstructed Slip Dress

Ann Demeulemeester, $http://bit.ly/MgBqZf
Silver Bead and Black Staeen Zip Clutch

Silver Bead and Black Staeen Zip Clutch

BCBG Maxazria, $81
Textured Cropped Trousers

Textured Cropped Trousers

Phillip Lim, $395


Peter Pilotto for Target, $35
Maxi Cami Dress

Maxi Cami Dress

Nili Lotan, $495
State Of Being Organza Pencil Skirt

State Of Being Organza Pencil Skirt

Asos, $234
Cairo Jumper

Cairo Jumper

Reformation, $258
Luncheon Shirt

Luncheon Shirt

MinkPink, $62
Gold Panther Printed Neoprene Sweatshirt

Gold Panther Printed Neoprene Sweatshirt

Clover Canyon, $246
Gabi Varsity Jacket

Gabi Varsity Jacket

Club Monaco, $398
Strapless Jumpsuit

Strapless Jumpsuit

Rachel Roy, $69
EXPLORE: Peter Pilotto for Target, Club Monaco, Mango, Minkpink, Rachel Roy, Phillip Lim, Nili Lotan, Reformation, BCBG Maxazria, Clover Canyon, ASOS, Ann Demeulemeester, How To, Trends, Anna Friel, Alexa Chung, Arizona Muse, Cara Delevingne, Dree Hemingway, Jessica Alba, Jourdan Dunn, Karlie Kloss, Kate Bosworth, Kate Moss, Olivia Palermo, Suki Waterhouse


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