Playing dress up

We’re heading up to New York next week to visit the in laws and are going to actually go out one night.  In the city.  By ourselves.  Without children.  We’re going to get to go out with some friends we haven’t seen in far too long.  The last time we were out in the city I was just starting the cycle that brought me S.  So we’re talking almost 4 years now.  While this is all very exciting, it brings with it a very big anxiety producing stressor….what the hell to wear?????

Nothing cute I own from years ago fits.  And if it did it’d probably be horribly outdated.   I’ve started to pick up some new clothes and are cute and fit well but that is by stay at home mom standards. Right now all I’m usually going for is a semi-put together look.  As in not yoga pants and a t-shirt.  I know that even my nicest, cutest, stay at home gear is not appropriate for a night out in the city. 

The whole thing is even further complicated by the fact that I have NO idea what one wears anymore for a night out.  Cute embellished top with nice jeans?  Was always my go to in the past but like I said that was a long time ago.  The very LAST thing I want to do is look like someone who never gets out and is trying to hard.  (so basically I don’t want to look like myself).  I just bought a cute long sweater to wear with leggings or skinny jeans…would that work?  Or is it too much like pajamas?  ( I know the answer to that question…I bought it expressly because it is an acceptable pajama replacement)  Flats or boots….ahhhh….too many choices and too little fashion sense!

What would you wear?  Budget has to be kept in mind and that budget is painfully small right now. (thank you Congress for pretending it is possible to balance the budget on the backs of federal workers)  But tell me what types of things I should think about and I can take it from there…thanks


September 23, 2011. Uncategorized.


  1. Sunny replied:

    I feel your pain. I just got back from Target. They had some cute dresses and little sweaters. I needed something too. Now just wondering if the dress will fit. BLAH! Good luck!

  2. Mel replied:

    I am so not the one to ask because I have NO fashion sense, but I’d go for a pair of swingy black pants and a simple top. J. Jill sometimes has great things on their sales rack at the mall.

  3. HereWeGoAJen replied:

    I think a long sweater with skinny jeans sounds good. And I’d vote flats, skinny jeans always look cute with flats.

  4. Rebecca @ Unexplained X2 replied:

    I love the skinny jeans (just got my first pair this year) with boots…and a cute top/jacket/sweater…whatever you feel comfortable in. You’ll look great no matter what! Enjoy!

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