This may be cheating since the sweater is new (to me, secondhand via TRR) and thus doesn't need to be reimagined.
Uptown:
Proenza Schouler sweater. Fun zipper detail: it doesn't stop at a neckline, so when you're not wearing it, you can zip it completely closed.
Downtown:
Tech skirt I've had for years now - a collab between Nike and Alyx with lots of fun straps, zips, and pockets all over.
Leggings and my trusty Vince combat boots.
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