STYLETHREAD -- LET'S TALK SHOP!

Theater attire is pretty much anything goes these days, especially at matinees.  I would try to put together an outfit that is fairly casual and laid-back but something that you would still feel comfortable wearing at night if you are planning to go to some bars.  Maybe cropped pants with a cute tank and nice flats or low wedges or something involving a plain skirt and kitten heels.

As for where to go afterwards, I should have some ideas especially since I work in the theater district but I am clueless.  I tend to prefer dive-y places.  I'm sure others will have suggestions for you.  Actually here's some advice - I would probably say it's best to get out of the Times Square area and head to Chelsea or the village but the W in Times Square (it's on Bway and 47th) has the Whiskey which is hip and super popular - normally it can be hard to get in but since you'll be there earlier you shouldn't have trouble.  There's also at least one other bar in the same hotel.  I went to one on an upper floor which had a futuristic vibe and was pretty cool. 

OOoh sounds exciting!

El Ray is on 14th bt 7th and 8th on the south side of 14th. It's a restaurant, Mexican, but attracts a wide crowd... this was a favorite drinking hole for me and my gallery girlfriends when I worked in Chelsea. It's hip but not overly trendy/moderny hip.

The margaritas are not cheap (pitcher is like $26) but between two people it will last the whole evening and all of the drinks are made with fresh fruit juices! My favorite flavor is watermelon.

Also the backyard is always crowded in the summer, and if you're a smoker, it's rare in NYC to smoke/drink/eat all in one place. Get the fish fajitas (this is sharable b/t two people). It's delicious.

Here's the CitySearch info on it. Link

Like cc, I prefer dive-er places and often feel weird about recommended fun/funky bars to people because the places I like the most aren't necessarily the chicest places around. If you're in the midtown area, I would say you have better luck at hitting up dive-y/sh*tholes in Hell's Kitchen like Bellvue Bar or Siberia Lounge for cool/not cool vibe. But you might want to say to hell with it and go to the View Bar in the Marriott hotel (it's rotating restaurant) if you want to get a quick drink before the show.

Anyway, whatever you decide have an excellent time. Let me know if you have any other questions.

Oh yeah as far as dress... you haev to realize that most people who go to see Broadway shows/plays are usually from out of town and dress comfortably, as they probably have been sight-seeing all day. I would dress more for the bars than for the show.