jennifer aniston little black dress in 🐈‍⬛🖤 Jennifer Aniston Takes NYC in

After two consecutive losses (both of which Swift witnessed in person), the team is heading to Massachusetts for the match-up

Deciding how to style it is half the fun: Pair it with flat sandals and a light button-up for a relaxed daytime vibe, or dress it up with slingback heels and a chic car coat

A short trip allows you only to brush against something much deeper, to briefly touch a city that continues to reveal itself long after you've left

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Aniston has occasionally worn outfits that fall outside of her typical style, but this asymmetric number is one of her bolder looks