Pretty well anything goes when you’re walking around NYC but the City also offers superb occasions for dressing up, way more than most places.
One of them has just happend. It’s the Jazz Age Lawn Party held early in June each year on Governor’s Island in NYC harbor. As you can see from the video everything 1920′s jazz is the rule and think what opportunities that offers for a dedicated dresser upperer.
Of course the 2 biggies are Halloween and ComicCon. All seriosu NYC dressers-up treasure these 2 events and invest hours, indeed months making sure they have noteworthy costumes so they are the darlings of the instagram set during both events.
But NYC is very accepting of casual dressing in totally weird costumes. Dressing in a strange way and riding the subway at the same time is almost ho hum, but still a lot of fun. Then there’s turning up at a late night diner, ditto. One of the rules of NYC behavior is that you do NOT notice a weird costume which broadens the scope of what you can do in the dressing up department
Then there’s special street parties and special medieval festivals where you can shake out your favorite Game of Thrones outfit. Or you can decide to walk around the town as a zombie. There’s the Easter Parade and Valentines Day, though just make sure your loving partner is in on it if you do the Valentine’s day thing.
Bottom line, NYC facilitates dressing up however you please, wherever you please so go for it.