Meghan Markle in white pencil skirt and silk shirt on June 9

Meghan Markle, Jume 9 2026 Instagram

WHAT SHE WORE: Meghan wore silk shirt from Matteau, white pencil skirt from Posse and Sarah Bray sun hat

BUY:

SKIRT: POSSE EMMA PENCIL SKIRT

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Posse Emma pencil skirt

Bella Hadid in blue jacket and black pencil skirt on January 14

 

Bella Hadid in New York City on January 14 2026

WHAT SHE WORE: Bella wore blue Saint Laurent jacket, black pencil skirt from Saint Laurent, black Saint Laurent sunglasses and black Saint Laurent slingback pumps

BUY:

SKIRT: SAINT LAURENT PAPERBAG PENCIL SKIRT IN COATED COTTON

SUNGLASSES: SAINT LAURENT SL 853 ESTHER

BAG: SAINT LAURENT MOMBASA MEDIUM IN LEATHER

SHOES: SAINT LAURENT AMALIA SLINGBACK PUMPS

Hailey Bieber in dark navy jacket and pencil skirt on July 16

 

Hailey Bieber on July 16 2025, Instagram

WHAT SHE WORE: Hailey wore dark navy fitted jacket from Alfie, dark navy pencil skirt from Alfie and black Gucci sandals

BUY:

JACKET: ALFIE THE CAPRI PANTS

SKIRT: ALFIE THE ALMA JACKET

SANDALS: VINTAGE GUCCI BY TOM FORD SANDALS

Lauren Sanchez in denim pencil skirt and denim bodysuit and white Balenciaga cup bag on March 26

 

Lauren Sanchez in Studio City on March 26 2025

WHAT SHE WORE: Lauren wore denim bodysuit from Alaia, denim Alaia pencil skirt and white Balenciaga cup clutch

BUY:

TOP: ALAIA DENIM SLEEVELESS BODYSUIT

SKIRT: ALAIA HIGH RISE DENIM PENCIL SKIRT at Mytheresa at Residenza725

BAG: BALENCIAGA 9 AM CLUTCH WHITE at Balenciaga at Bloomingdale's at FWRD at Saks Fifth Avenue

Rosie Huntington-Whiteley in beige cropped jacket and pencil skirt on September 3

 

Rosie Huntington-Whiteley on September 3 2024

WHAT SHE WORE: Rosie wore beige cropped jacket from Wardrobe NYC, beige pencil skirt from Wardrobe NYC and white Balenciaga pumps

BUY:

JACKET: WARDROBE NYC PERFECTO COTTON CROP TRENCH JACKET at Saks Fifth Avenue at Ferfetch at Saks off 5th at FWRD

SHOES: BALENCIAGA SQUARE KNIFE PUMPS WHITE at Mytheresa

Melania Trump in black blazer and white pencil skirt on May 17

 

Melania Trump at Baron's graduation on May 17 2024

WHAT SHE WORE: Melania wore black Dior blazer, white pencil skirt from Michael Kors, Gucci straw hat and white Manolo Blahnik pumps

BUY:

BLAZER: DIOR 30 MONTAIGNE DOUBLE-BREASTED WOOL AND SILK BAR JACKET BLACK

SKIRT: MICHAEL KORS COLLECTION DOUBLE CREPE SABLE PENCIL SKIRT IN OPTIC WHITE

HAT: GUCCI GROSGRAIN-TRIMMED GLITTERED STRAW HAT

SHOES: MANOLO BLAHNIK BB PUMPS WHITE SUEDE

Meghan Markle in floral embroidered cardigan and pencil skirt on November 8

 

Meghan Markle in San Diego on November 8 2023

WHAT SHE WORE: Meghan wore floral embroidered cardigan from Carolina Herrera and pencil skirt from Lafayette 148 New York

BUY:

CARDIGAN: CAROLINA HERRERA EMBROIDERED POPPY WOOL CARDIGAN

SKIRT: LAFAYETTE 148 NEW YORK RAFFERTY NOUVEAU CREPE MIDI SKIRT

Meghan Markle in black top and black pencil skirt on May 15

 

Meghan Markle on May 15 2023, Archewell Foundation

WHAT SHE WORE: Meghan wore black sweater from Another Tomorrow and black pencil skirt from Lafayette 148 New York

BUY:

TOP: ANOTHER TOMORROW RIB KNIT HENLEY TOP

SKIRT: LAFAYETTE 148 NEW YORK RAFFERTY NOUVEAU CREPE MIDI SKIRT

Emily Ratajkowski in yellow tiger skirt and brown cropped shirt on October 15

 

Emily Ratajkowski at SNL afterparty on October 15 2022

WHAT SHE WORE: Emily wore brown cropped shirt, yellow tiger print pencil skirt from Dolce & Gabbana, knee high Khaite boots and Louis Vuitton shoulder bag

BUY:

SKIRT: DOLCE & GABBANA TIGER PRINT PENCIL SKIRT

BOOTS: KHAITE DAVIS KNEE HIGH BOOTS at Mytheresa at Net-a-Porter at FWRD

BAG: LOUIS VUITTON DAMIER EBENE CANVAS RECOLETA SHOULDER BAG

PHOTO: BACKGRID

Alessandra Ambrosio in neon yellow knit sweater and metallic midi skirt at Balmain Festival on September 29

 

Alessandra Ambrosio at Balmain Festival in Paris during Paris Fashion Week on September 29 2021

WHAT SHE WORE: Alessandra wore neon yellow oversized knit sweater from Balmain, metallic silver pencil skirt with zipper from Balmain, neon yellow clutch and metallic pumps

BUY:

SWEATER: BALMAIN CROPPED CABLE-KNIT TURTLENECK SWETAER at The Webster at Luisaviaroma at Net-a-Porter

SKIRT: BALMAIN METALLIC ZIPPER MIDI SKIRT

PHOTO: GETTY

Kylie Jenner in red check crop top and skirt on May 1

Kylie Jenner on May 1 2020, Instagram

WHAT SHE WORE: Kylie wore red check print crop top from Charlotte Knowles and red check print skirt from Charlotte Knowles

BUY:

TOP: CHARLOTTE KNOWLES SKINN TOP

SKIRT: CHARLOTTE KNOWLES SKINN DRESS

PHOTO: ©KYLIE JENNER/INSTAGRAM

Meghan Markle in burgundy sweater, red leather skirt and burgundy pumps on October25

Meghan Markle Duchess of Sussex at Windsor Castle on October 25 2019

WHAT SHE WORE: Meghan wore burgundy sweater from Joseph, red leather skirt from Boss and burgundy suede Sarah Flint pumps

BUY:

SWEATER: JOSEPH DEEP V-NECK PULLOVER

SKIRT: BOSS SELRITA SKIRT IN RUBY

PUMPS: SARAH FLINT PERFECT PUMPS 100

PHOTO: ©PA

Olivia Palermo in yellow floral print midi skirt and white tee on September 3

Olivia Palermo on September 3 2019

WHAT SHE WORE: Olivia wore white t-shirt and yellow floral print midi skirt from Miu Miu

BUY:

SKIRT: MIU MIU RUCHED FLORAL PRINT CLOQUE MIDI SKIRT

PHOTO: ©OLIVIA PALERMO/INSTAGRAM

Rosie Huntington-Wihteley in pink bodysuit and denim pencil skirt on August 27

Rosie Huntington-Whiteley on August 27 2019

WHAT SHE WORE: Rosie wore pink bodysuit from Zara, denim pencil skirt from Wardrobe NYC, Bottega Veneta mesh pumps, cream Bottega Veneta clutch and black Celine sunglasses

BUY:

SKIRT: WARDROBE NYC X LEVI'S HIGH RISE DENIM MIDI SKIRT

SHOES: BOTTEGA VENETA MESH AND CHAIN SQUARE TOE STRETCH PUMPS at Matchesfashion at Bottega Veneta

BAG: BOTTEGA VENETA THE POUCH CLUTCH BAG

SUNGLASSES: CELINE EDGE SUNGLASSES

PHOTO: ©ROSIE HUNTINGTON-WHITELEY/INSTAGRAM

Rosie Huntington-Whiteley in white top and black pencil skirt in LA on August 19

Rosie Huntington-Whiteley in Los Angeles on August 19 2019, Instagram

WHAT SHE WORE: Rosie wore white bodysuit from Zara, black pencil skirt from Wardrobe NYC, white strappy sandals from Bottega Veneta, beige leather clutch bag from Bottega Veneta and black Celine cat eye sunglasses

BUY:

TOP: ZARA HALTER BODYSUIT

SKIRT: WARDROBE NYC RIBBED STRETCH KNIT TUBE SKIRT

SANDALS: BOTTEGA VENETA LEATHER SANDALS WHITE

BAG: BOTTEGA VENETA THE POUCH BAG

SUNGLASSES: CELINE CAT-EYE SUNGLASSES

PHOTO: ©ROSIE HUNTINGTON-WHITELEY/INSTAGRAM

Katie Holmes in blue shirt and brown patent leather pencil skirt in New York on March 14

Katie Holmes in New York City on March 14 2019

WHAT SHE WORE: Katie wore blue shirt from Dorothee Schumacher, brown patent leather midi skirt from Zeynep Arcay, beige suede ankle strap pumps and Gucci suede embroidered bag

BUY:

SHIRT: DOROTHEE SCHUMACHER NEO OVERSIZED SHIRT BLUE

SKIRT: ZEYNEP ARCAY PATENT LEATHER PENCIL SKIRT

CLUTCH: GUCCI OPHIDIA EMBROIDERED SUEDE SHOULDER BAG

PHOTO: ©BACKGRID

Olivia Palermo in silver sequin pencil skirt and green checked jacket at Milan Fashion Week

Olivia Palermo at Milan Fashion Week on September 19 2018

WHAT SHE WORE: Olivia wore green checked bomber jacket, white top, silver sequin midi skirt from Sally LaPointe and green leather ankle strap booties

BUY:

SKIRT: SALLY LAPOINTE NEW SEASON

SHOES: JIMMY CHOO LARK ANKLE STRAP BOOTIES GREEN at Nordstrom at Bergdorf Goodman

PHOTO SOURCE: GETTYIMAGES

Meghan Markle in green leather skirt and green shirt in Chichester on October 3

Meghan Markle Duchess of Sussex with Prince Harry visiting Chichester, West Sussex on October 3 2018

WHAT SHE WORE: Meghan wore beige Emporio Armani cashmere coat, green leather Hugo Boss pencil skirt, green silk shirt from & Other Stories, beige suede Stuart Weitzman pumps and green Gabriela Hearst bag

BUY:

COAT: EMPORIO ARMANI CASHMERE DOUBLE CLOTH COAT WITH CLASSIC LAPELS

SKIRT: HUGO BOSS LAMBSKIN LEATHER PENCIL SKIRT GREEN

SHIRT: & OTHER STORIES STRAIGHT FIT SILK SHIRT

PUMPS: STUART WEITZMAN HAZE SUEDE LEGEND PUMPS

BAG: GABRIELA HEARST NINA BAG

photo source: dailymail/shutterstock/wireimage

Kylie Jenner in green crop top and green pencil skirt in Paris on June 22

Kylie Jenner in Paris on June 22 2018

WHAT SHE WORE: Kylie wore green crop top and matching green pencil skirt from Fendi and Andy Wolf sunglasses

BUY:

TOP AND SKIRT: FENDI NEW SEASON

SUNGLASSES: ANDY WOLF OPHELIA FRAMELESS SUNGLASSES

photo: instagram @kyliejenner

Kate Middleton in red blazer and red pencil skirt in Hayes on April 20

WHO: Kate Middleton at the opening of the Global Academy in Hayes on April 20 2017

WHAT SHE WORE: Kate wore red ruched blazer from Armani, red pencil skirt from Armani, beige pumps and beige Etui clutch

BUY:

BLAZER: ARMANI COLLEZIONI RUCHED BLAZER

SKIRT: ARMANI COLLEZIONI PENCIL SKIRT RED at Gilt Groupe at Farfetch