From School Runs to Stiletto Icons: SJP’s Edgy Cutout Boots and Her Style Evolution

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Sarah Jessica Parker has long been synonymous with the whimsical, high-fashion aesthetic of her Sex and the City persona.

Sarah Jessica Parker out with her twins Marion Broderick and Tabitha Broderick in West VillageSarah Jessica Parker out with her twins Marion Broderick and Tabitha Broderick in West Village, New York City, on May 20, 2013 (Credit: TNYF / WENN)

However, her real-world street style often leans into a more pragmatic, “tomboy chic” territory. A prime example of this stylistic departure occurred on May 20, 2013, in New York City’s West Village, when the actress was spotted prioritizing edge and comfort for a morning school run.

Sarah Jessica Parker's 5-pocket Current / Elliott skinny jeans have topstitched patches and shredded holes for a well-worn lookSarah Jessica Parker’s 5-pocket Current / Elliott skinny jeans have topstitched patches and shredded holes for a well-worn look

Sarah Jessica Parker grounds her relaxed West Village school-run look with chunky black cutout ankle boots, adding structure and edge to distressed boyfriend jeans and a casual layered topSarah Jessica Parker grounds her relaxed West Village school-run look with chunky black cutout ankle boots, adding structure and edge to distressed boyfriend jeans and a casual layered top

She wore slouchy, torn Current/Elliott boyfriend jeans and a dark jumper under a blazer, paired with cutout, buckled ankle boots.

Close-up of Sarah Jessica Parker's stylish booties featuring a unique mix of blue, black, and snakeskin texturesClose-up of Sarah Jessica Parker’s stylish booties featuring a unique mix of blue, black, and snakeskin textures

We love the booties’ combination of blue, black, and snakeskin, but we think the footwear made her look too manly.

Sarah Jessica Parker's unconventional shoe choice sparks mixed reactions during her NYC outingSarah Jessica Parker’s unconventional shoe choice sparks mixed reactions during her NYC outing

The shoes would have been better if balanced with a more feminine outfit. Either that or she should have worn feminine shoes (like pumps or ballet flats) with her ensemble.

Detailed view of Sarah Jessica Parker's trendy cutout buckled booties, spotted in the West VillageDetailed view of Sarah Jessica Parker’s trendy cutout buckled booties, spotted in the West Village

The Everlasting Footprint of Sarah Jessica Parker’s Style

While the trends of 2013—like the heavy, buckled “tomboy” boot—evolve, SJP’s core philosophy remains unchanged: fashion is a playground for experimentation. From her early days as a Manhattan trendsetter to her current status as a global footwear mogul, her ability to mix high-concept silhouettes with practical street style makes her a permanent fixture in the fashion zeitgeist.

To see how her style has evolved from these West Village school runs to the red carpets of today, explore our curated archive of her most iconic looks:

👠 Explore Sarah Jessica Parker’s Best Shoe Moments: