Olivia Palermo's 65 Best Outfits Ever

The style star is an endless source of fashion inspo.

Photo:

Edward Berthelot / Getty Images

Whether she's sitting front row at a fashion show or simply taking a stroll in NYC's Soho, Olivia Palermo is a sight to be seen. For over a decade now, the socialite and entrepreneur has been serving up a constant stream of fashion inspiration that has us looking to her as our style compass. During her many globe-trotting adventures, Palermo has nailed every look from off-duty to haute couture. It's what makes her style moments so major. To celebrate the fashion it-girl, we're rounding up her best outfits of all time.

Keep scrolling for Olivia Palermo's 65 most stylish looks ever.

01 of 65

March 6, 2023

Olivia Palermo in a denim maxi skirt and shirt with tapered sleeves

Edward Berthelot / Getty Images

Palermo stepped out at Paris Fashion Week in head-to-toe denim. From her oversized V-neck shirt with tapered sleeves to her midi skirt with gold hardware, the results were seamless.

02 of 65

March 4, 2023

Olivia Palermo in a black turtleneck and checked jacket with maxi skirt

Marc Piasecki / WireImage / Getty Images

Palermo arrived at the Elie Saab show during Paris Fashion Week in checked separates, a black turtleneck, and strappy sandals.

03 of 65

March 3, 2023

Olivia Palermo in black and white dress suit with bowtie

Stephane Cardinale - Corbis / Getty Images

At the Giambattista Valli show, Palermo wore a black and white coatdress with fringe details and a perfectly placed headband.

04 of 65

February 25, 2023

Olivia Palermo in oversized purple sweater and black flared skirt

Robino Salvatore / GC Images / Getty Images

Palermo made heads turn by pairing an oversized embellished purple sweater with a pleated black skirt during Milan Fashion Week.

05 of 65

February 22, 2023

Olivia Palermo in a beige suit with zip-up turtleneck blouse

Alessandro Levati / Getty Images

Olivia Palermo stuck to an all-neutral palette, pairing pleated wide-leg trousers with a matching blazer and sheer zip-up. Platform sneakers elevated her monochrome outfit.

06 of 65

February 21, 2023

Olivia Palermo in a gray oversized blazer with sequins and black pants with slits

 Jacopo Raule / Getty Images

The fashionista chose to throw her oversized pinstriped blazer over black trousers with slits at the ankle.

07 of 65

October 3, 2022

Olivia Palermo in an orange pattern coat, cropped jeans, and white loafers

Daniel Zuchnik / Getty Images

Outside the Zimmermann show during Paris Fashion Week, Palermo sported a statement jacket by Zimmermann along with cropped jeans, white loafers, and cat-eye sunnies.

08 of 65

September 25, 2022

Olivia Palermo in printed maxi skirt and jacket with black crop top

Daniele Venturelli / WireImage / Getty Images

Palermo was a vision at the Ferrari fashion show wearing a black crop top and colorful printed separates.

09 of 65

April 6, 2022

Olivia Palermo in a green neon skirt suit with brown puffer coat and overcoat vest

Gotham / GC Images

Palermo was all about the layers when she stepped out in New York City's Soho. Neon green separates made up the base of her outfit while a brown puffer jacket and long vest finished off the look.

10 of 65

February 12, 2022

Olivia Palermo in a white turtleneck cutout dres

Gotham / WireImage

Palermo struck a pose at the PatBo fashion show during New York Fashion Week in this white turtleneck dress with cut-outs.

11 of 65

September 8, 2021

Olivia Palermo in a bright pink knotted suit jacket and strappy sandals

Jared Siskin / Getty Images

Palermo promoted pink fashion, footwear, and makeup while at the Cinq à Sept show during New York Fashion Week.

12 of 65

February 22, 2020

Olivia Palermo in a mustard yellow sweater and brown maxi skirt

Arnold Jerocki / Getty Images

Palermo was embracing sweater weather at Milan Fashion Week wearing an oversized mustard knit, brown midi skirt, and chunky nude boots.

13 of 65

September 21, 2019

Olivia Palermo in a black bondage dress

Stefania M. D'Alessandro / Getty Images

Palermo gave off glamorous BDSM vibes when she showed up to the amfAR Gala in this black satin number complete with straps and sky-high slit.

14 of 65

March 3, 2018

March 3, 2018
Pierre Suu/Getty Images

The It-girl was spotted outside of the Elie Saab show wearing a black and white poncho over a pleated dress. Black over-the-knee boots solidified another perfect outfit.

15 of 65

March 2, 2018

Olivia Palermo in a bright pink skirt, black top, and military-style jacket
Christian Vierig/Getty Images

Olivia Palermo draped the coat that she designed with Banana Republic over a black sweater, which was tucked into a Balmain skirt and paired with Dior boots.

16 of 65

February 27, 2018

Olivia Palermo in a gray overcoat
Christian Vierig/Getty Images

Who cares what's underneath your jacket when you've got a coat like Palermo's Dior number?

17 of 65

February 25, 2018

Olivia Palermo in a sweater, faux fur coat, and leather track pants
Melodie Jeng/Getty Images

Palermo knows that an all-black outfit doesn't have to be boring. Here, she paired a Brunello Cucinelli sweater with a Cara Mila faux fur jacket, leather pants, and flats.

18 of 65

February 24, 2018

Olivia Palermo in metallic python bomber jacket, a multi-toned leather skirt, and red boots
Timur Emek/Getty Images

Palermo had fun with a Brunello Cucinelli metallic python bomber jacket, a multi-toned leather skirt, and red boots.

19 of 65

February 23, 2018

Olivia Palermo in a peach top and rolled up tan pants with white sneakers
Christian Vierig/Getty Images

Palermo made this head-to-toe Tod's outfit look cool by pairing it with sneakers.

20 of 65

February 19, 2018

Olivia Palermo in an orange sweater with a yellow sash and leather pants
Christian Vierig/Getty Images

During London Fashion Week, Olivia kept warm in an orange sweater with a yellow sash. Leather J. Brand jeans and Sophia Webster Felicity boots rounded out her winning outfit.

21 of 65

February 11, 2018

Olivia Palermo in a black and white striped blouse, black blazer, and cropped trousers
Daniel Zuchnik/Getty Images

Palermo put her own twist on a classic suit by styling it with a stripe top (notice the red details on the sleeves) and slip-on sneakers.

22 of 65

January 22, 2018

Olivia Palermo in a Valentino jacket paired with a ruffle top, skirt, and combat boots
Melodie Jeng/Getty Images

Palermo served us an extra dose of style with this cool Valentino jacket paired with a ruffle top, skirt, and combat boots.

23 of 65

January 22, 2018

Olivia Palermo in a red Dior suit and beige Prada boots
Edward Berthelot/Getty Images

We're in love with Palermo's red Dior suit, and her Prada boots are just as amazing.

24 of 65

October 3, 2017

Olivia Palermo in a green and black jacket with ripped jeans
Edward Berthelot/Getty Images

Mixed shades of green were the highlight of this picture-perfect street-style outfit. But we'd be remiss not to mention Palermo's purple Fendi sunglasses.

25 of 65

October 1, 2017

Olivia Palermo in a red coat over a white and red Valentino dress
Jacopo Raule/Getty Images

Olivia Palermo teamed up with Banana Republic to design this statement coat, which was paired with a Valentino dress.

26 of 65

September 28, 2017

Olivia Palermo in a beige cable-knit sweater, vest, cropped trousers, and teal pumps
Edward Berthelot/Getty Images

Palermo stuck to mostly tan tones with a Balmain sweater and Max Mara sleeveless jacket and pants. But her favorite Jimmy Choo pumps added a punch of color.

27 of 65

April 10, 2017

April 10, 2017
Splash News

In Manhattan, the style star elevated a sweatshirt and sneakers like only she can. She paired a simple white crewneck with bejeweled Roger Vivier sneakers, a quilted off-white coat, and a tea-length skirt, giving the outfit a pop of color with a blush Elena Ghisellini satchel and purple-tinted sunnies.

28 of 65

February 20, 2017

Olivia Palermo in a black ruffled coat, sheer striped top, and leather leggings
Timur Emek/GC Images)

Palermo took London Fashion Week by storm in a ruffled coat, sheer striped top, and leather leggings. She polished off the chic look with a neck scarf and black booties.

29 of 65

February 20, 2017

Olivia Palermo in a floral print dress over leather leggings
Christian Vierig/Getty

The fashion icon was spotted outside of the Erdem LFW show in a floral print dress over leather leggings. She topped off the chic cold-weather look with a black scarf and heeled booties.

30 of 65

February 20, 2017

Olivia Palermo in an orange turtleneck, brown skirt, and blue loafers, with a sweater tied over her shoulders
Neil Mockford/GC Images

Palermo looked perfectly preppy during LFW in an orange turtleneck, embellished skirt, and blue loafers, with a burnt orange sweater tied over her shoulders.

31 of 65

February 19, 2017

Olivia Palermo in a white ribbed turtleneck and asymmetrical skirt and black coat
Timur Emek/Getty

Palermo made white work after Labor Day in a ribbed turtleneck and asymmetrical skirt during London Fashion Week. She topped the monochromatic look with a long black blazer and patent combat boots.

32 of 65

February 13, 2017

Olivia Palermo in a printed plush coat, ripped skinnies, and pointy booties
Gilbert Carrasquillo/GC Images

The style star looked chic during NYFW in a printed plush coat, ripped skinnies, and pointy booties.

33 of 65

January 24, 2017

Olivia Palermo in a military-style coat with a conductor hat and track pants
Edward Berthelot/Getty

Only Palermo could mix and match like this. She paired a military-style coat with a conductor hat and track pants for an unexpected look in Paris.

34 of 65

January 6, 2017

Olivia Palermo in a navy blue velvet trench coat and over-the-knee boots
Alo Ceballos/GC Images

Palermo was walking her Maltese, Mr. Butler, in a navy blue velvet trench coat and a set of over-the-knee boots. She topped her wintry look with a simple black beanie.

35 of 65

January 5, 2017

Olivia Palermo in a double-breasted army green wool military coat over an ankle-length turtleneck dress
Robert O'neil/Splash News

The modern style icon stepped out in Brooklyn wearing a faux double-breasted army green wool military coat over an ankle-length turtleneck dress. Palermo amped up her look with classic black boots, rose-colored shades, and a deep crimson handbag by Longchamp.

36 of 65

November 14, 2016

Olivia Palermo in a buttoned navy coat with ruffled sleeves with wide-leg trousers
Robert Kamau/GC Images

Palermo was sailor-chic for dinner in Manhattan, pairing a buttoned navy coat with ruffled sleeves with wide-leg trousers. She topped off the look with a graphic clutch and black booties.

37 of 65

October 18, 2016

Olivia Palermo in a red dress, leather motorcycle jacket, and combat boots
Jackson Lee/Splash News

Palermo went rocker chic in N.Y.C. in a red dress, leather motorcycle jacket, and combat boots. She polished off the edgy look with a studded choker and waist-defining leather belt.

38 of 65

October 2, 2016

Olivia Palermo in an off-the-shoulder sweater with colorful printed maxi skirt
Jacopo Raule/GC Images

The queen of making unexpected pairings look endlessly chic rocked an off-the-shoulder striped sweater and tropical print skirt to Paris Fashion Week. Never one to shy away from color, she topped off the look with beige and black sandals and a colorful clutch.

39 of 65

September 30, 2016

Olivia Palermo in a sheer lace top and wrap skirt
Pascal Le Segretain/Getty Images

Palermo donned an unexpected navy lip for Paris Fashion Week, pairing the bold hue with a sheer lace top and wrap skirt.

40 of 65

September 23, 2016

Olivia Palermo in a collared blouse and printed midi skirt
Christian Vierig/Getty Images

Palermo looked perfectly polished during Milan Fashion Week in a collared blouse and printed midi skirt.

41 of 65

September 18, 2016

Olivia Palermo in track pants, a turtleneck sweater vest, and white ruffled long sleeves
Christian Vierig/Getty Images

Palermo makes track pants look so chic when paired with a turtleneck sweater vest and white ruffled long sleeves. She topped off the daring look with a fishtail braid and oversize sunnies.

42 of 65

September 14, 2016

Olivia Palermo in white button-down with light gray sweater and jeans with fringe details
Jared Siskin/Patrick McMullan via Getty Images

Thanks to O.P., fringed jeans are now a thing. The style setter paired the unexpected pants with a button-up shirt and layered sweater during NYFW.

43 of 65

August 19, 2016

Olivia Palermo in a white blouse with a leopard-print pocket, ripped skinny jeans, and yellow flats
Splash News

The street style star paired a Zara blouse with a leopard-print pocket with ripped skinny jeans and yellow flats.

44 of 65

July 6, 2016

Olivia Palermo in a black studded dress with tulle skirt and jacket
Dominique Charriau/WireImage

The style icon strolled her way into Russian model Natalia Vodianova's fifth annual "Art of Giving" Love Ball wearing a ballerina-inspired tulle dress with studs. She styled the frock with a sporty over-the-shoulder jacket and sky-high strappy pumps paired with sheer black tights and a braided 'do.

45 of 65

July 4, 2016

Olivia Palermo in hothouse florals and earthy neutrals
Michael Ip/Runway Manhattan

Palermo was seen during Couture Fashion Week wearing a striking mix of hothouse florals and earthy neutrals. The star paired a floral skirt with a yellow shirt and topped off the look with a green jacket.

46 of 65

June 23, 2016

Olivia Palermo in a navy blue jacket over a black midi dress
Franziska Krug/Getty Images

Palermo proved that black and navy can work together by layering a blue jacket over a black midi dress. She topped the look off with strappy black sandals and a colorful clutch.

47 of 65

June 15, 2016

Olivia Palermo in black leather pants with a black and white chiffon blouse and a colorful Fendi handbag
JENY / Splash News

The entrepreneur strolled across Manhattan's Upper East Side in a bold look. She paired black leather pants with a black and white chiffon blouse and standout accessories, like her colorful Fendi handbag.

48 of 65

June 2, 2016

Olivia Palermo in a white jumpsuit and off-white trench coat
BFA/REX/Shutterstock

The socialite went monochrome for an event in N.Y.C. in a white jumpsuit and off-white trench.

49 of 65

May 25, 2016

Olivia Palermo wearing a navy top with white separates and Stella McCartney platform brogues
Charles Roussel/BFA.com

The fashion influencer attended Piaget's Possession Collection in New York wearing crisp tailored white separates with Stella McCartney platform brogues. She accessorized her look with a delicate pink Adornmonde choker and stunning pieces from the new Piaget Possession Collection.

50 of 65

April 20, 2016

Olivia Palermo in a t-shirt, duster, and skinny jeans
Michael Simon/startraksphoto.com

Palermo hit the streets of New York City wearing a relaxed V-neck from Old Navy in light heather gray. She paired the tee with black Paige skinny jeans, a breezy draped trench coat, ankle-strap Jimmy Choo heels, an envelope clutch, and oversize sunnies.

51 of 65

April 7, 2016

Olivia Palermo in a black hoodie and red sports jacket with "Olivia" on the back
Splash News Online

The fashionista sported an off-duty look perfect for an overcast spring day, hitting the streets of NYC in a personalized red satin jacket with "Olivia" written on the back of it, along with a gray top and jeans.

52 of 65

March 5, 2016

Olivia Palermo in red shirt, fuzzy cream vest, printed pants, and booties
Christian Vierig

At Paris Fashion Week, Palermo wore a cream fuzzy vest over a cherry red silk blouse to combat the cold. Her tribal print trousers were just the right amount of boho, and the cropped detail showed off the dainty laser-cut detail on her pointy-toe black booties.

53 of 65

January 25, 2016

Olivia Palermo in a plaid dress and thigh-high boots
Pascal Le Segretain/Getty Images

Wearing a plaid mini-dress, Palermo redefined school-girl style in thigh-high boots and sunnies.

54 of 65

January 10, 2016

Olivia Palermo in a green, red, and white, strapless A-line dress
John Shearer/Getty Images

In a Delpozo knee-length dress at the Golden Globes, Palermo's look stood out on the red carpet.

55 of 65

December 9, 2015

Olivia Palermo in a tan satin dress with dual slits
Jason LaVeris/FilmMagic

The stylish socialite donned a tan dress with dual slits for a red-carpet event in Beverly Hills.

56 of 65

December 7, 2015

Olivia Palermo in a black Valentino gown with gold detailing
Monica Schipper/FilmMagic

Palermo stunned in a Valentino gown while attending a red carpet event honoring Valentino in New York City.

57 of 65

November 3, 2015

Olivia Palermo in head-to-toe denim with a long vest
Pacific Coast News

Palermo stepped out with hubby Johannes Huebl in the West Village in N.Y.C. in her preferred off-duty uniform: denim on denim. But she gave her chambray shirt-and-skinnies combo a fall-ready take by topping it with a wool two-tone sleeveless coat and caramel brown croc pumps. The finishing touches? Tortoiseshell shades and a bright cherry red duffel affixed with a fluffy pom charm.

58 of 65

September 10, 2015

Olivia Palermo in a colorful floral gown and red pumps
Splash News

Palermo sizzled in a bold lip and floral gown with fiery red pumps while attending an event in London.

59 of 65

July 22, 2015

Olivia Palermo in a tucked Chambray shirt and destroyed denim skinny jeans
Splash News

Palermo prevailed once again, ruling the New York City streets in a chambray monogrammed Rails shirt that she casually half-tucked into a pair of destroyed skinnies.

60 of 65

July 20, 2015

Olivia Palermo seen wearing a blue printed dress while walking in New York City
Splash News

Palermo's sartorial greatness remains intact even in 90-plus-degree weather. She brought her impossibly chic, not to mention melt-proof, aesthetic to the streets in a summery blue-multi watercolor-esque Tularosa top tucked into a matching Tularosa flared mini. She topped off her look with hot-weather staples, like tortoiseshell shades, an easy golden yellow bucket bag, a chilled bottle of Evian water, and comfy snakeskin ballet flats.

61 of 65

January 26, 2015

Olivia Palermo in a flowy berry-colored dress with high neckline
Joe Schildhorn/BFA/REX/Shutterstock

The former reality star slipped into a berry-colored, flowing gown for an evening out while attending Paris Fashion Week.

62 of 65

June 3, 2015

Oliva Palermo in an all-black outfit with open shoulders and strappy heels
Raymond Hall/GC Images

While running errands in NYC, Palermo stuck to mostly black with an open-shoulder blouse and loose trousers. She added a hint of color with a python tote and white sunglasses.

63 of 65

December 9, 2014

Olivia Palermo in a black top, gold sequined skirt, and blazer
MICHAEL SIMON/Startraksphoto

The street style star got into the holiday spirit at the Piperlime holiday party in a gold-dipped Piperlime Collection knit that she layered over a high-shine sequined Milly skirt, styling the two with a sharp tuxedo jacket, a black clutch, and ankle-strap heels.

64 of 65

December 4, 2014

Olivia Palermo in a white top and orange maxi skirt with slit
David M. Benett/Getty Images for Monica Vinader

At the Monica Vinader London flagship launch party, Palermo gave her summery orange maxi skirt a winter-ready spin by pairing it with a crisp white long-sleeve neck-tie blouse, black opaque tights, and over-the-knee leather boots. A studded belt (for a touch of edge), a printed clutch, and a selection of Monica Vinader pieces completed her look.

65 of 65

November 14, 2014

Olivia Palermo in a white top, black leather jacket, and floor-length skirt
Victor Chavez/WireImage

Palermo hit the House of Herrera runway show and gala in Mexico City in an elegant white asymmetrical CH Carolina Herrera blouse with a navy silk evening skirt, lending edge with a black leather jacket draped over her shoulders, Dior earrings, and a black clutch.

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