A Look Back On 20 Years Worth Of It Girl Footwear

In the beginning, there was Manolo Blahnik. The Spanish cobbler’s “big break” came when Vogue’s legendary editor Diana Vreeland told the budding artist to “make things; make shoes!” and… well… he did. Carrie Bradshaw ran through the streets of New York (and Los Angeles, and Paris, and then back to New York…) in his famously delicate stilettos, and name-checked them with the same urgent frequency of a teen trying to get backstage at Coachella. (Renowned Vogue editor-in-chief Anna Wintour also has worn the brand exclusively for the last several decades.) Thus, the ornate heels became fashion’s first status shoes in recent history.

This was 20 years ago, and wherever Sex and the City went, pop culture followed. Cupcakes transformed from a 3^rd grade birthday treat to an upscale symbol of feminine floof; checked-out men became prizes instead of prenup lessons. As for footwear? It basically became the fashion crowd’s modern Bat signal, projecting their vibes — and style allegiance — with every step.

A lot’s changed since 2002. Beyoncé is now the queen of everything. (Yay.) Blockbuster no longer rents videos. (Boo.) But shoes are still the tribal banners of the show-goer world, and with every Fashion Week, a new coveted sole mate emerges. Below is a rundown of the last two decades of them, many of which are still available and worth shopping on vintage and secondhand sites around the internet. Because — with zero apologies to another fictional fashion enforcer, Regina George — vintage really is so adorable.

2002: Manolo Blahnik Satin Bejeweled Heels

Decadent and deceptively high, these Carrie Bradshaw staples became a coveted accessory for millions of fashion fans after appearing in HBO’s 2002 ad campaign for Sex and the City’s fourth season. Steve Madden, Aldo, and Nine West all made knockoffs, and when Wicked began its Broadway run several years later, Glinda (originally played by Kristin Chenoweth) showed off a similar pair during her famous “Popular” solo.

2003: Sigerson Morrison High-Heeled Boots

With help from bootleg jean fatigue (and a few early Laguna Beach looks), a new combo emerged on the street style front: baggy jeans sucked tight into shiny, high-heeled boots. Maggie Gyllenhaal did it in the Marc Jacobs front row; Kelly Hu did it at an Imitation of Christ show; Gisele did it while zooming backstage before Victoria’s Secret fashion show. And of course, we all did it while heading to a Phantom Planet concert. You could get a spike heel boot anywhere, but fashion editors swore by the ones from Sigerson Morrison because of their perfect fit and reputation for always selling out.

2004: Ugg Boots

I saw Sienna Miller wearing Ugg boots and a vintage Biba dress in 2004 … so I bought Ugg boots and a vintage Biba dress in 2004? Um, absolutely. China Chow, Nicki Hilton, and a legion of runway models wore them to Fashion Week, too … and it’s still happening, albeit with way more flair, thanks to filmmakers like Amalie Gassmann.

2005: Imitation of Christ x Easy Spirit Gladiator Sandals

Before Versace paired with H&M and Missoni came to Target, Tara Subkoff partnered with Easy Spirit on a pair of gladiator sandals that were the style trifecta: comfortable, sexy, and candy for street style photographers.

2006: Chloe Block Wedges

The case for Phoebe Philo Supremacy starts now, when the designer — then 32 — sent wooden wedges down the Chloé runway that were immediately claimed by Christy Turlington and Victoria Beckham. Even a famously adorable runway stumble by Jessica Stam in the shoes couldn’t stop their heat.

2007: Christian Louboutin Black Suede Stiletto Boots

Sometimes, the shoe is the outfit. Such was the case for Christian Louboutin’s thigh-high stiletto boots, which came in a variety of colors and textures (shiny! suede! Croc!) and helped fuel the new truth that leopard print is a neutral. Eva Mendes and Jennifer Lopez each stopped traffic while wearing them at Fashion Week.

2008: Chanel Gun Stiletto

In March of 2008, the late legend Karl Lagerfeld debuted The Miami Vice Shoe, a lovely stiletto anchored with a handheld pistol. Part Warhol, part Tarantino, the shoes were produced in tiny quantities and given to select muses by Mr. Lagerfeld himself. “When I saw him after the [Chanel] show in Paris, he said, ‘I want you to keep those,’” says Leigh Lezark, the DJ and model who’s frequently seen in the brand’s chicest pieces. “He said, ‘We didn’t produce many. As it turns out it’s difficult to ship tiny guns,’ and then he looked around the Grand Palais and continued with, ‘Better on you than one of these creatures.’ He had an amazing sense of humor and ability to make you feel like the only person in the room.”

Lezark traveled home with the shoes, “which were definitely a street style moment on their own,” and was stopped by French security because they spotted the fake fashion pistols in her bag. “All of my stuff was searched!” Lezark says. “Luckily, the Parisian airport security could tell they weren’t a threat; they were fashion.”

The late socialite and reality star Tara Palmer-Tomkinson wasn’t so lucky. In 2013, she was detained by Swiss police after bringing the heels to the Zurich airport — although apparently, she charmed the police so much during her arrest, they ended up playing Backgammon with her until her flight came.

2009: The Yves Saint Laurent Cage Heel

Maybe fashion is a prison; maybe people really just loved the hint of bondage in these teetering pieces of leather. Either way, the YSL cage heel sparked enough of a frenzy that the Los Angeles Times proclaimed them the shoe of 2009, and street style stars seemed to agree.

2010: The Burberry Shearling Boot

An elevated take on the shaggy boho boots of yore, Burberry’s shearling spike heel boot was fully lined, ensuring you could stay warm while also looking absolutely amazing. Designed by style superstar Christopher Bailey, the bootie debuted on Joan Smalls before appearing on Mary-Kate Olsen and Zanna Roberts Rossi.

2011: The Valentino Rock Stud Heel

I’m a little bit couture; I’m a little bit rock n’ roll; I’m obviously the Valentino Rockstud, which came as high heels, low heels, or flats… and boosted the brand’s margins by 36%. Created by Pierpaolo Piccioli and Maria Grazia-Chiuri (who now helms Dior), the shoes had fans like Emma Stone and Olivia Palermo… and also Shein, which (surprise?) totally knocked them off.

2012: The Chloé Susannah Boot

The year is 2013, and Miranda Kerr is a Victoria’s Secret bombshell married to Orlando Bloom. Inherently likeable and famously sweet, the moon-faced model was such a style icon that the Bling Ring robbed her house — but they didn’t manage to get the most practical of all designer scores, The Chloé Susannah boot. Studded with a floral gold pattern, these luxury staples launched the idea of “French Girl Chic,” and while Parisians like Marion Cotillard and Clémence Poésy wore them, so did Americans like Halle Berry, Kate Bosworth, Emma Roberts, and throngs of models (like Lily Aldridge) as they bounced from show to show. Versatile and easygoing, they are still a best-seller on The RealReal.

2013: The Stan Smith

In the fall of 2013, Adidas asked Naomi Campbell and Kate Moss to create contemporary art pieces for a London gallery show, with Stan Smith sneakers as their inspiration. It didn’t take long for stylists and models to follow suit in Paris and beyond. Today, Stan Smiths are industry shorthand for “I actually don’t feel like going to this fashion show, but once I get there it’ll be fabulous, so I’d better look amazing.”

2014: The Brother Vellies Springbok Slide

The author of the upcoming Token Black Girl, Danielle Prescod is always a street style “get” for photographers. But when the writer, stylist, and consultant arrived at the Spring 2015 shows in a pair of Brother Vellies springbok slides, the response was next level. “I’d done a piece for ELLE on [designer] Aurora James — it was their first American press,” she says. “Aurora sent me a pair and they were just so unusual! Also, they were a flat shoe but also a statement piece, which is the reason I loved them so much… I think any show that makes you feel comfortable has viral street style potential.” Indeed, James’s hit shoes sparked the fuzzy sole trend that fueled Gucci’s grinch mules later that year. Her latest collection continues to embrace a wild softness that can pair with jeans or formalwear.

2015: The Stella McCartney Platform Brogue

So cute, so easy to wear… and so hard to buy, thanks to their instant appeal. That might explain why they took a full year to become a street style staple, but once they did, wow. They went casual, they went boyish, they went artsy, they went posh, they went punk, they went wild, and they went hard for the case that sustainable luxury fashion is here to stay.

2016: The Gucci Loafer

Investing in a Gucci piece is expensive, but the cost-per-wear on these loafers is pretty much flawless. They vibe vintage without being costume-y; they convey effort but not insecurity; they are beautifully crafted to last and Dakota Johnson approved. If you’re not down with a heel—even a small one — steer yourself to their flats instead.

2017: The Saint Laurent Diamond Boot

It took exactly one week for Saint Laurent’s killer sparkle boots to go from the runway to Rihanna, and after that, game over. Anna Della Russo wore them and literally stopped traffic later that September, and nobody has seen them since because they have been reclaimed by sexy space aliens and taken to another galaxy. (Ok fine, they’re here, and if you have $8k you can buy them. Otherwise — space aliens, I’m serious.)

2018: The Prada Flame Shoes Return!

Miuccia Prada didn’t have to revive the Prada flame shoes of 2011 in neon colorways, but she did that for us. Kitschy, cool, and desperately expensive, the soles first hit the runway in 2012. Katy Perry got first dibs on the initial go-round; Kendall Jenner brought back the heat with the revival.

2019: The Dior Ribbon Pump

It was hard to avoid these logo-stamped shoes, as seen on the runway and then on Bella Hadid, Natalie Portman, and Stranger Things Natalia Dyer. But they’re so lovely and easy to wear, why would you want to?

2020 Pre-Pandemic: The Off-White Nike

To be honest, we all knew the vibes were off. Reports of a “coronavirus” were magnifying after every fashion show, models were posting selfies wearing masks (if they—or we—could even find masks!) and by the end of Paris Fashion Week, everyone just wanted to race home. Only one thing could save us in our darkest hour: The reassuring, steady cool of Off-White’s Nike trainers. OK, also, science and Dr. Fauci. But, like, metaphorically…

2020 Post-Apocalypse: Birkenstocks + LL Bean hiking socks

Gigi does it. Kaia does it. We do it. We love it. (There’s also the tie-dye sock and Chanel sandal option, if you’re fancy.)

2021: The Miu Miu Stomper Boot

Miu Miu’s micro-minis and cropped sweaters got the most media attention in 2021, but another viral hit was on the coveted brand’s hands… wait, we mean feet. It’s a shoe we’ll affectionately call “the stomper,” and it comes as an ankle bootie or a knee-high boot. When paired with the brand’s winsome party wear or fuzzy poufs, it’s a shoe that brings girly fantasy down to earth. When worn with piles of ‘90s grunge finds — like teen pop star Bella Poarch — it’s a message that girls may want to have fun, but they want to stomp the patriarchy even more.

2022: Virtual Reality

Bottega Veneta’s rubber-rimmed Chelsea boot is a take-no-prisoners staple for the current fashion pack, with Khaite’s white cowboy bootie — a throwback to the ‘80s dream girls of Can’t Buy Me Love and Ferris Bueller — close behind. Meanwhile, Marc Jacobs Heaven’s grunge-meets-mod kiki boot is a verified obsession for Gen Z shoppers. But for those looking far into the future might check out the emerging style star Masie Wilen, who designs for Clueless characters if they lived in space — or as she puts it, “cool femininity.” Her last collection debuted in the metaverse (really), and with it came a Keds collaboration that mixes pixelated swirls with pastel puffs. “I designed them to be a feminine and sleek counter to the oversized masculine sneakers dominating the market for the past years,” she tells TZR. And because they’re actually affordable, they’re compatible with both virtual reality and actual reality. Soled? Sold!