I found myself Googling this exact phrase on Saturday prior to a night out in Downtown Orlando with a group of girls 3-4 years my junior. I have 2 closets full of clothes and shoes and yet I had no idea where to even start. Once you make it into your mid-twenties, what’s okay and what will get your ass put on “What Not To Wear”?

Google had very little to offer me in the form of advice. I did come across a blog that talked about starting to upgrade your wardrobe with higher quality pieces as opposed to running in to Forever 21, rolling around and coming out with whatever sticks to you. I don’t have time for this nonsense. Sure, I’ll consider it in the future but this is a “9pm on a Saturday? problem, not a “meeting in a few days” problem.

What makes a woman of my age look too immature and what makes me look like an old lady? Of course, I know not to go out in a damn pants suit (which makes me cringe and is something I don’t plan to own any time soon) but what’s the cut off for wearing short dresses and crop tops? So many questions…

So then I thought about the people I would be hanging out with and the people I would see throughout the night.  There’s nothing that sets me apart from these younger girls that would throw up red flags so fuck it. By no means do I fall into the category of being old and I’ve got a decent body.  I’ll wear whatever I want.  

Look at Carrie from Sex in the City. If she can wear that shit I can push the boundaries a little. For the night I’ll go out in a tight, short dress and wedges and I’ll rock it. I could have done worse.

In general, yeah my closet needs an update from post-college twenty-something to professional 26 year old woman but who’s counting? And who has the time for all of that? Or the money for that matter? Do I have to become one of those women that go shopping for practical pieces that can be a versatile addition to my closet? Barf. Give me a mini skirt, a tank top and a pair of sky-high heels and call it a day.