Kendall Isnt Wearing Flared Jeans With Heels or Flats—Shes Wearing Cool Anti-Trend Boots

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In case you’ve been wondering what Kendall Jenner and Jacob Elordi would wear for a perfect fall day in NYC, we now know. The It couple was just spotted in the city, with Elordi in a hoodie and Jenner in a men’s field jacket from The Row and a draped leopard-print scarf (a combination I, for one, will be copying). The rest of Jenner’s outfit also included a noteworthy combination that I wanted to put on your radar.

You can’t talk about winter 2026 (and 2027) denim trends without naming flared and bootcut jeans at the top of the list. Jenner chose a vintage-inspired blue denim pair for the couple’s outing, and if you want to look as cool as she does in flared jeans, skip the trendy flats and heels and go with an anti-trend pair of flat boots like Jenner’s. Hers were a simple leather pair with a low stacked heel (as flat boots often have). They’re no-frills—just simple and cool, which is exactly how you could describe Jenner’s style. Keep scrolling to shop the look and similar boots to wear with your flared jeans.