I enjoy wearing equestrian-inspired outfits in the fall, and this season I am especially attracted to such looks due to all the tall boots and turtlenecks trending. Beyond the classic, skinny jeans/pants tucked into tall boots look, I would like to wear an updated version of the Tailored Equestrian ensemble I linked to. The equestrian jacket and layering top part would remain the same, I am interested in possible updates to the trendy bottoms + trendy shoes part. 5 years ago, the recommendation was cropped kick flares/culottes + sleek booties. This is still perfectly current/relevant (proof that trends change slower these days), but I am wondering about updates. One thing that comes to my mind is the chunkier/lug sole footwear. I found the outfits below with cropped kick flares and chunky loafers with socks, and I am quite smitten with them.

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