We’re not here to criticize pregnant women who wear heels — everyone has their own comfort levels. Wearing flats can be downright painful for some, especially those with high arches.
However, as empathetic beings, we can’t help but feel for the moms-to-be who, in their final trimester, balance bulging baby bumps, curved spines, and swollen feet on slender stilettos. While they may claim they’re comfortable, it doesn’t always seem that way from the outside looking in.
Here are 20 heavily pregnant celebrities who rocked high heels well into their last trimester. Were they doing it as part of a contractual obligation, for a publicity photo-op, or simply for the love of fashion? Let’s find out.
1. Kim Kardashian’s Memorable Struggle: Swollen Feet in Stilettos
Kim Kardashian made it to our worst shoe disasters list for wearing heels despite visibly swollen feet when she was pregnant with baby North.
Pregnant Kim Kardashian stuns in a chic Givenchy open-sleeve midi dress paired with Albertina Podium heels and a Lanvin crocodile-effect leather clutch during her visit to Naimie’s Beauty Center on May 16, 2013 (Credit: Adriana M. Barraza / Anwar Hussein / Arnold Wells / Daniel Tanner / Ivan Nikolov / Judy Eddy / Lia Toby / FayesVision / SIPA / WENN / HRC)
During her pregnancy, Kim Kardashian experienced significant swelling in her feet and ankles, a common condition known as edema. Despite this, she wore high heels, notably a pair of Givenchy sandals with clear straps.
Photographs from May 2013 show her feet visibly swollen and tightly strapped into these heels, leading to discomfort and public concern. The clear straps of the sandals accentuated the swelling, making it more noticeable.
Kim Kardashian turns heads in a Kardashian Kollection faux leather cocktail dress and Givenchy Bird Cage ankle booties at her Sears in-store appearance for the Kardashian Kollection at Willowbrook Mall in Houston, Texas, on May 4, 2013
2. Kate Middleton: Regal in Suede Heels During Her Final Pregnancy Days
Right before Catherine, the Duchess of Cambridge gave birth to Prince George, she and her nearly nine-month baby bump had to attend one last engagement in black suede heels.
Kate Middleton dazzled at the Princess Cruises Naming Ceremony on June 13, 2013, wearing a Hobbs Dalmatian Mac coat, Sylvia Fletcher hat, Annoushka pearl drop earrings, Episode Angel pumps, and her iconic Garrard sapphire engagement ring
3. Victoria Beckham: Powering Through Pregnancy in Iconic Louboutins
Victoria Beckham is not known for her smile. Still, she looked downright miserable when she attended the Royal Wedding six months pregnant and wearing painful-looking Christian Louboutin “Daffodile” platform pumps.
Victoria Beckham stunned at the Royal Wedding at Westminster Abbey on April 29, 2011, in a sleek Victoria Beckham dress, a Philip Treacy hat, Christian Louboutin Daffodile platform pumps, and a matching Victoria Beckham clutch
4. Beyoncé’s Bold Footwear: Towering Heels and Hidden Baby Bumps
Beyoncé hid the size of her baby bump well with scarves and jackets, but we could still see how high her heels were.
Beyoncé Knowles stepped out in New York on October 24, 2011, wearing a chic Bottega Veneta Athena scarf, J Brand maternity leggings, and Alexander McQueen thick-platform pumps
This is how 8-year-old Beyoncé looked when performing “Home” from “The Wiz” in a Peoples’ Workshop talent competition.
8-year-old Beyoncé performing “Home” from “The Wiz” in a Peoples’ Workshop talent competition
5. Angelina Jolie’s Glamorous Pregnancy Look in Open-Toe Heels
Even the usually pragmatic Angelina Jolie wore heels at one point in her pregnancy with her twins, Knox Léon and Vivienne Marcheline.
Angelina Jolie exudes elegance in a tailored Dolce & Gabbana black suit paired with Taryn Rose peep-toe pumps at the Changeling photocall during the 2008 Cannes Film Festival in Cannes, France
6. Gwen Stefani’s Edgy Pregnancy Style: High-Heeled Boots with a Twist
Gwen Stefani loved her Dr. Martens–inspired heels so much that she couldn’t give up wearing them in her last pregnancy with son Apollo Bowie Flynn.
Gwen Stefani steps out in Beverly Hills on December 27, 2013, showcasing a chic Zara kimono top with elbow-length sleeves, paired with black L.A.M.B. Nichol booties and Karen Walker Number One sunglasses
7. Drew Barrymore: Smiling Through Pregnancy in Elegant Heels
We see Drew Barrymore trying hard to smize with a huge nine-month baby bump while wearing high heels.
Drew Barrymore glows in a vintage Ludwig Boutique yellow shift dress with floral embroidery and a silk hem, paired with woven sandals at the Warner Bros. Pictures event during CinemaCon 2014 at Caesars Palace in Las Vegas on March 27, 2014
8. Kerry Washington’s Sparkling Pregnancy Moment in Studded Louboutins
Just a month after walking the 2014 Oscars red carpet in studded Louboutins, Kerry Washington gave birth to daughter Isabelle Amarachi.
Kerry Washington dazzled at the 2014 Oscars on March 2 in a custom Jason Wu amethyst satin crepe gown with a side slit and gold tie-bar detail, paired with Jennifer Meyer jewels, embellished platinum pumps, a vampy oxblood lip, and a wavy half-up, half-down hairstyle
9. Kate Winslet’s Radiant Red Carpet Look in ‘Angelique’ Louboutins
Kate Winslet carried her seven-months-pregnant belly in a red Jenny Packham gown and Christian Louboutin “Angelique” peep-toe pumps well.
Kate Winslet glowed on the red carpet at the Labor Day premiere during the 2013 BFI London Film Festival on October 14, wearing a stunning red Jenny Packham dress, Christian Louboutin shoes and bag, and De Beers jewelry while proudly cradling her baby bump
10. Alyson Hannigan’s Charming Red Carpet Moment in Peep-Toe Heels
Alyson Hannigan and her then seven-month baby bump were obligated to grace the American Pie premiere.
Alyson Hannigan shined at the American Reunion premiere on March 19, 2012, at Grauman’s Chinese Theatre in Hollywood, flaunting her baby bump in a sparkly green dress paired with black heels
11. Melissa George’s Stylish Pregnancy Choice: Strappy Sandals at CNN Heroes
Melissa George was brave enough to wear heels while pregnant at the 2013 CNN Heroes: An All-Star Tribute event.
Melissa George radiated elegance at the CNN Heroes event on November 20, 2013, flaunting her baby bump in a taupe top paired with a high-low pleated white skirt and nude high-heeled sandals, completing the look with vampy red lipstick as she neared her due date
A pregnant Melissa George showed off her feet in high heels
12. Kate Hudson’s Triple-Platform Glamour: Pregnancy Chic in Casadei Pumps
Kate Hudson confidently showcased her baby bump in glamorous fashion, gracefully rocking high-heeled, triple-platform Casadei slingback pumps that elevated her maternity style to a whole new level.
Kate Hudson glowed in a gold stretch silk and crystal-embroidered strapless gown by Stella McCartney while attending the Alexander McQueen: Savage Beauty Costume Institute Gala at the Metropolitan Museum of Art in New York City on May 2, 2011
13. Rachel Zoe’s Fierce Pregnancy Style: Leopard-Print Booties in Action
There seems to be no way Rachel Zoe will ever give up wearing heels, especially ones as beautiful as her Brian Atwood “Didier” leopard-print booties.
At 38 weeks pregnant, Rachel Zoe stepped out in Beverly Hills on March 14, 2011, exuding her signature chic style in an all-black ensemble, including leggings, a flowing cardigan, a floppy hat, oversized sunglasses, and leopard-print platform booties
14. Hilary Duff’s Casual Yet Bold Look in Maison Margiela Booties
Hilary Duff marched straight to her ob-gyn’s office in Maison Martin Margiela open-toe booties.
Hilary Duff was spotted leaving a doctor’s appointment on February 9, 2012, wearing a chic Alexander McQueen silk patchwork logo scarf, a Stella McCartney tailored boyfriend blazer, Maison Martin Margiela belted open-toe booties, Ashley Pittman light horn quill earrings, a Celine Boston bag, a maternity T-shirt from A Pea in the Pod, and David Lerner signature leggings
15. Reese Witherspoon’s Graceful Pregnancy Style in Versace Sandals
While pregnant, Reese Witherspoon made walking on the red carpet in Versace platform sandals look graceful.
Reese Witherspoon dazzled at the Mud premiere during the Cannes Film Festival on May 26, 2012, wearing a custom-made cobalt blue Versace gown adorned with sparkling embellishments, paired with Versace strappy platform sandals
16. Kristin Cavallari: Snapping Back in Style With Stilettos
Kristin Cavallari and her slim figure snap in and out of pregnancy, so stiletto heels are no big deal in comparison.
Kristin Cavallari looked stunning at the 22nd Annual Elton John AIDS Foundation Oscar Party on March 2, 2014, wearing a chic Balmain black lace mini dress paired with classic Christian Louboutin Pigalle 120 pumps
17. Holly Madison’s Playful Glam: Pregnancy in Platform Stilettos
Holly Madison was another celebrity who had to wear platform stilettos while pregnant.
Holly Madison dazzled at the red carpet grand opening of the CeeLo Green Is Loberace show at Planet Hollywood Resort & Casino in Las Vegas on March 2, 2013, wearing a vibrant blue asymmetrical dress paired with sparkling Christian Louboutin Samaria Strass pumps
18. Kendra Wilkinson’s Bold Pregnancy Look in Sleek Black Pumps
Not to be one-upped by Holly Madison, fellow former Playboy playmate Kendra Wilkinson proved she could rock heels while heavily pregnant.
Kendra Wilkinson looked radiant at the Jennifer Love Hewitt Celebrates the Release of Her New Baby Collection with A Pea in the Pod event in Beverly Hills on April 2, 2014, wearing a chic black lace dress paired with classic black pumps
19. Jessica Simpson’s Fabulous Maternity Footwear: Studded Pumps Edition
As her name is a shoe brand, it’s Jessica Simpson’s job to wear fabulous shoes, pregnant or not.
Jessica Simpson dazzled at the NBC Universal Winter TCA Press Tour All-Star Party on January 6, 2012, wearing a stunning Dolce & Gabbana sequined cotton net dress paired with edgy Christian Louboutin Asteroid spike-toe pumps
20. Jennifer Lopez’s Head-Turning Pregnancy Look in Thigh-High Boots
While not yet in the last trimester, Jennifer Lopez was pregnant with twins when she arrived at the Ed Sullivan Theater in New York City to appear on David Letterman.
Jennifer Lopez, pregnant with twins, stepped out in style outside the Ed Sullivan Theatre for the Late Show With David Letterman in New York City on October 9, 2007, wearing a chic black coat paired with thigh-high Christian Louboutin boots and a statement chain-accented hat
She covered her baby bump with an oversized pea coat and sported high-heeled thigh-high boots.
Jennifer Lopez adds a bold edge to her look with an S&M-inspired black leather cap featuring a striking gold chain detail
Pregnancy doesn’t mean compromising on style. Many expectant mothers have embraced their changing bodies by choosing fashionable lingerie and high heels, blending comfort with elegance. For inspiration on maintaining your style during pregnancy, explore our feature on expectant moms who confidently wore sexy lingerie and high heels. Additionally, discover how Zoe Saldana showcased her baby bump in chic Kurt Geiger sandals, exemplifying that maternity fashion can be both comfortable and glamorous.