A Cool Girl's Guide To Nighttime Dressing

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

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 Jewellery, and an Edie Parker Lara Clutch ($995).

Cara Delevingne


Neil P. Mockford/FilmMagic

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).

Ann Demeulemeester

Deconstructed Slip Dress ($269) in Black

?Topshop Wool Boyfriend Coat ($196) in Bright Orange 

Kate Moss



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

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

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).

Alexa Chung


Neilson Barnard/Getty Images for Target

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).

Peter Pilotto for Target Skirt ($35)

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).

Arizona Muse


JB Lacroix/WireImage

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).

Suki Waterhouse


David M. Benett/Getty Images

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).


Cairo Jumper ($258) in Black Floral

Olivia Palermo


Mireya Acierto/Getty Images

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).

Luncheon Shirt ($62) in Pink

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

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).

Karlie Kloss


Dara Kushner/INFphoto.com

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).

Club Monaco

Gabi Varsity Jacket ($398) in Rum Raisin

Anna Friel


David M. Benett/Getty Images for InStyle

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.

Rachel Roy

Strapless Jumpsuit ($69) in Navy