Petite & Perfect: Kelly Osbourne’s Chicest High-Heel Looks Over the Years

Please subscribe to our newsletter to receive updates from Your Next Shoes. This post may contain affiliate links. Please see our disclosure for more details.

Kelly Osbourne has always believed that confidence is the key to great style, once saying, “Dress how you feel and love what you wear because at the end of the day you have got to wear and feel great in it.”

Despite being shorter than the average American woman at 5 feet 1 ¾ inches (156.8 cm)—compared to the national average of 5 feet 4 inches (162.6 cm)—she has never let height define her fashion choices.

With a US shoe size 7, Osbourne effortlessly uses bold footwear to make a statement, proving that style isn’t about size—it’s about attitude.

Kelly Osbourne at the 2013 BeautyCon Fashion and Beauty Summit held in HollywoodKelly Osbourne exuded edgy sophistication at the 2013 BeautyCon Fashion and Beauty Summit in Hollywood, rocking a curve-hugging black leather dress, metallic pointed-toe pumps, and her signature lilac locks styled in soft waves on August 24, 2013 (Credit: FayesVision / WENN)

Kelly Osbourne on Body Image: “I Would Never Consider Myself Fat”

The singer has mentioned in various interviews and on her Twitter account that she doesn’t consider herself overweight. She stated in an interview that she typically weighs around 120 pounds and has humorously remarked that she’s 5 feet 2 inches tall on a good day.

I was a UK size ten (American size six) and I was 5ft 2in. I’m short, so of course I’m going to look that bit bigger than someone who is 5ft 4in and a size ten. But I would never have considered myself as fat.

Kelly Osbourne carries her son Sidney Osborne Wilson while stepping out in black leather pants, a fitted sweater, and cozy platform UGG Tazz slippers at Craig's restaurant for best friend Daniel Nguyen's birthday celebrationKelly Osbourne carries her son Sidney Osborne Wilson while stepping out in black leather pants, a fitted sweater, and cozy platform UGG Tazz slippers at Craig’s restaurant for best friend Daniel Nguyen’s birthday celebration on October 12, 2024 (Credit: BauerGriffin / INSTARimages)

On Your Next Shoes, you can see photos of Kelly Osbourne boosting her height in heels by footwear brands such as Aldo, Paul Andrew, and Saint Laurent.

Kelly Osbourne’s Standout Shoe Moments: From Classic to Edgy

Kelly Osbourne has never shied away from bold fashion choices, often making a statement with her footwear selections. Here are some of her most memorable shoe moments:

  • Aldo: At the Material Girl launch event, Kelly embraced a spring-ready look by pairing a light denim jacket, a high-waist floral print skirt, and a polka-dotted top with classic peep-toe Aldo pumps, blending vintage charm with modern sophistication.
  • Alexander McQueen: She added an edgy touch to her look at the Young Hollywood Awards with studded Alexander McQueen pumps, complementing her signature purple hair.
  • Brian Atwood: During the Topshop Topman LA launch party, she dazzled in sparkling sequin pants paired with classic black satin Brian Atwood ‘Hamper’ pumps, showcasing her knack for blending classic pieces with contemporary trends.
  • Paul Andrew: At Cosmopolitan’s 50th Birthday Celebration, Kelly paired a sleek black jumpsuit with Paul Andrew ‘Chrysler’ pumps, adding elegance to her edgy aesthetic.
  • Saint Laurent: At a high-profile launch, she turned heads with metallic green lipstick and Saint Laurent ‘Opium’ pumps, proving her fearless approach to style.

While Kelly is known for her daring hairstyles, she also made a statement with her footwear at Cosmopolitan’s 50th Birthday Celebration. Pairing her edgy look with sleek Paul Andrew pumps, she proved once again that her shoe game is just as bold as her fashion choices.

Kelly Osbourne Rocks Edgy Hairstyle at Cosmopolitan’s 50th Birthday Bash

Kelly Osbourne made a striking statement with her daring and unconventional purple side-shaved top bun during Cosmopolitan’s 50th Birthday CelebrationKelly Osbourne made a striking statement with her daring and unconventional purple side-shaved top bun during Cosmopolitan’s 50th Birthday Celebration at Ysabel in West Hollywood on October 12, 2015 (Credit: FayesVision / WENN / Nicky Nelson / 3rd Eye)

In October 2015, Kelly Osbourne joined Kim Kardashian West, Khloé Alexandra Kardashian, and Kylie Jenner at Cosmopolitan’s 50th Birthday Celebration at Ysabel in West Hollywood, California. How do you like her purple side-shaved top bun?

Kelly Osbourne rocks an edgy purple side-shaved top bun, exuding confidence and bold styleKelly Osbourne rocks an edgy purple side-shaved top bun, exuding confidence and bold style

The then-30-year-old British singer-songwriter, actress, television presenter, and fashion designer sported a baggy jumpsuit styled with a pair of Paul Andrew pumps that we spotted earlier in the year on Emmy Rossum.

Kelly Osbourne stuns in a black jumpsuit paired with sleek pointed-toe heels and her signature purple side-shaved top bun at Cosmopolitan’s 50th Birthday BashKelly Osbourne stuns in a black jumpsuit paired with sleek pointed-toe heels and her signature purple side-shaved top bun at Cosmopolitan’s 50th Birthday Bash

Kelly Osbourne has a distinctive pair of tattoos on her feet. They are blue skull and crossbones designs, with one depicting a male skull featuring a yellow lightning bolt on the forehead and the other a female skull adorned with a red bow.

Kelly Osbourne sports a unique pair of blue skull and crossbones tattoos on her feet, one marked with a yellow lightning bolt and the other with a red bow, symbolizing male and female skulls respectivelyKelly Osbourne sports a unique pair of blue skull and crossbones tattoos on her feet, one marked with a yellow lightning bolt and the other with a red bow, symbolizing male and female skulls, respectively

As we’ve seen with Kelly Osbourne’s fearless approach to fashion, statement footwear plays a crucial role in defining personal style.

She’s not alone in her love for Paul Andrew’s designs—many other stylish celebrities have also stepped out in the brand’s iconic ‘Chrysler’ heels and other iconic shoe designs.

Stepping Out in Style: Celebrities Who Love Paul Andrew’s Heels

Here are some of the most memorable moments featuring these sculptural stunners:

Emmy Rossum’s Edgy Look at the CFDA Fashion Awards

  • Event: 2015 CFDA Fashion Awards
  • Outfit: Emmy Rossum stunned in a semi-sheer Dion Lee dress featuring daring cutouts and a plunging neckline.
  • Footwear: She elevated her ensemble with black suede Paul Andrew ‘Chrysler Zenadia’ pumps, known for their sculptural metal heels inspired by NYC’s Chrysler Building.
  • More Details: Emmy Rossum’s Zenadia Shoes Inspired by NYC’s Chrysler Building

Maggie Gyllenhaal’s Classic Black Ensemble at the NBR Gala

Emma Watson’s Sustainable Fashion Choice at the ‘Regression’ Photocall

  • Event: ‘Regression’ Photocall
  • Outfit: Emma Watson embraced sustainable fashion with a knitted black V-neck top and a multicolored tulle skirt from Christopher Kane’s Resort 2016 collection.
  • Footwear: She wore custom-made Paul Andrew black pumps, aptly named ‘Watson,’ reflecting her commitment to eco-friendly fashion.
  • More Details: Emma Watson Promotes Sustainable Fashion at ‘Regression’ Photocall

These fashion-forward moments reinforce why Paul Andrew’s ‘Chrysler’ heels remain a go-to choice for stylish celebrities. From bold architectural designs to classic elegance, these shoes prove that great footwear can be the defining element of an outfit—just as we saw with Kelly Osbourne’s standout looks.

These Art Deco-inspired stiletto heels from Paul Andrew are no longer available in stores. The heels have been lacquered and galvanized to prevent scratches.

Paul Andrew 'Chrysler' Over the Knee BootPaul Andrew ‘Chrysler’ Over-the-Knee Boots, $1,995

Paul Andrew Suede Chrysler Heel PumpPaul Andrew Black Chrysler Zenadia Pumps, $995

Paul Andrew Black Chrysler Suede Contrast-inset PumpPaul Andrew Black Chrysler Suede Contrast-Inset Pump, $1,395

Paul Andrew Black Suede Chrysler Ankle BootsPaul Andrew Black Suede Chrysler Ankle Boots, $1,395