Dressing for the Job - Adventures in Vintage

They say you should dress for the job you want, not the job you have.  In my case,  I need to start dressing for both the job I have and the job I want.  And that job is no job or, even better, self employment.  Now, after five years of long work weeks and hard-partying weekends, my wardrobe consists of boring work clothes (black dresses, button downs, Express Editor pants) and skanky dresses that will soon be inappropriate for me to wear ever (or possibly already are).  

I've always struggled with my casual look and have never focused on it too much.  I had no reason to.  Most of my weekend hours were spent in one of my skanky dresses and the rest of them I was probably either at the gym or too hungover to care what I wore to brunch.  Now that my days are going to be ruled by street clothes and I'm determined to keep it this way, so I figure I'd better go out and put together a wardrobe that screams "I am not the 9 to 5!" Something appropriate for strolling around town hoping for a glance of Lindsay Lohan hopping into her black Range Rover so I can later tell people we hang out in the same neighborhoods. 

After scanning my closet I quickly realized that my black turtle neck just wasn't going to cut it all winter.  So, armed with a sense of wonder, 50 bones and a Googled list of NYC Thrift stores, I headed out this afternoon to piece together my new 'drobe.  After picking up my new iPod Nano that I scored for $65 on Craigslist, I headed over to Cheap Jacks, the first stop on my Thrifty Tour.  In my head I composed a short list of must haves to craft my casual-persona.  A signature piece of Jewelry (something large and probably gold for around my neck), a bad-ass hat and a warm, slightly worn, jacket for the upcoming winter.  

Once inside Cheap Jacks, I was a little intimated by rack after rack of clothing - the place is huge - and headed over to the T Shirts.  Already detouring from my list, in a moment of temporary insanity, I picked up an Oregon Trail T-shirt and thought, "Eureka, this is the staple of my new look."  I quickly came to my senses and realized that I didn't want my new look to resemble that of a 30-rock writers room schlub.  Even as I eyed the racks of coats to my right, I couldn't resist the pull of the mounds of dresses to my left and veered even further off course.  I browsed through the 1950s, the '60,s and the '80s until to my surprise, it was the 70s rack that I pulled my first two items off of.  A plum-velvet fitted number with a scalloped neck and an easy-moving summery black number.  Striking at the right moment a friendly staffer offered to start a fitting room for me, and even though the one thing I do not need is dresses, I happily obliged.  I tried to to focus and spend some time looking at the type of items I actually need, but the pull of that little purple hotness was too much for me, so without picking up another item I all but sprinted to the fitting room.  Both dresses were glorious, but luckily or unluckily for me were too rich for my blood (the purple one was $65 and the black was $155).  That was when I learned that, even at Cheap Jacks, my tastes supersede my budget.  Empty handed, I thanked the helpful clerk who offered to pull some more dresses I don't need, and headed out the door.

My next stop was Housing Works on 23rd street.  The floor was bustling and I was convinced I'd score something in here and do a good deed at the same time since all of their proceeds go to charity.  Within two seconds of entering I scooped up a vintagey navy-blue Chuck Taylor jacket that was a measly $15 and thought, "Viola."  In true vintage-shopper style I ripped off my coat and dropped it, along with my bag, on the floor in the middle of the store and found the nearest mirror.  Much to my chagrin, the jacket was just too big and I haven't been unemployed long enough to learn how to sew, so I hung it back on the rack.  The rest of the selection at Housing Works was limited and reminded me of the bags of clothes I donate every couple of months, so I decided to move on.  

Continuing down 23rd street, I set my sites on my next target, 2nd Time Around - a Salvation Army outpost.  I thought to myself that I better at least find a good belt here.  I stepped in the door, saw the garbage bags of clothing lining the floors and promptly stepped back, turned around and left.  I can handle used clothing when it's on a rack, seeing it in bags that match the ones that I dump my snotty tissues into was too much for me to handle.  

Just down the street on Third Avenue was my final stop of the day, Vintage - The Thrift Store. Vintage is small, musty and slightly intimidating to me.  I had completely lost my sense of purpose, any grasp of my list and my mojo so when I saw the bus careening up the street, I dropped the driving gloves that I-don't-need-but-was-looking-at-anyway and sprinted to catch the M101.  

Safely on my way back to my generic Murray Hill neighborhood, I breathed a sigh of relief.  Sure, my shopping day was a bust, but I had a new iPod Nano in my bag and burning desire to get home, make myself some hot chocolate and upload the crap out of it.  I still have a few more vintage stores on my list and plan on pounding the pavement again this week in the hopes that I will find success.  Until then, I'll have to rock the same three outfits over and over again and just call them my "signature look" until I find the perfect $50 wardrobe.

Suggestions are welcome.