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Out and about | New York City, NY | June 26, 2023

Free People ‘Heartbreaker Skort’ – $78.00

Taylor isn’t a stranger to pairing short skirt hemlines with laceup oxfords (and cute socks). She’s been employing combos like this to schoolgirl-esque effect for years (most especially 2010-2011).

But this feels like a more up-to-date take on that pairing here in 2023.

The shirt is slouchier and oversized and notably not tucked in (that effect would have been a bit more prim, imo). The shoes are chunkier, as per current trends. The accessory that throws me most is actually the baseball cap where I would more expect to see Taylor in the similar (but different) fisherman or newsboy cap silhouette.

Overall, I love the cooler-toned blend of colours here, grounded by darker accessories and a very Taylor twist on trends.

Taylor also happened to wear this skirt in black last month – naturally continuing to be a high/low queen.

Worn with: Catbird NYC necklace, The Row shirt, Patou bag, Malone Souliers oxfords

Photo by Gotham ℅ Getty