Before you ask, yes, I did see Jake Gyllenhaal in the Village a couple weeks ago.  Yes, it was the best moment of my life. And yes, I am a celebrity whore. So sue me! In my defense, as if I needed one, I have been head over heels in love with the man since 1999 when he so effortlessly portrayed the innocent and adorable Homer Hickam in October Sky.

Anyway, because I have a rent check every month that costs more than my undergrad degree, I can’t just casually sit around drinking coffee in the Village on Mondays looking for attractive celebrities to stalk. I go to work. But what should you wear to work? Walking around midtown doesn’t really answer that question. Those Downtown 6 train commuters generally don’t know what’s up in the fashion department (Evidence: Last summer I was wearing a kick ass turban – they were on trend then – and a woman forcibly stopped me to ask me why I was wearing such an ugly thing on my head). While I do value their opinions (not), I wouldn’t ask these people what to wear, ever.

(Glasses: Warby Parker, Blouse: Equipment, Vest: Theyskens’ Theory, Pants: Alexander Wang, Watch: Michael Kors)

I generally dress a little more untraditional at my office, but this outfit can transcend many a work environment.  My job allows me a little more freedom in attire, but I always make sure to dress appropriately. I leave my tube tops and booty shorts at home. For my birthday, my grandparents bought me these Alex Wang pants which are possibly the best gift any girl could ask for in 2012. The deli man below my building agrees with me on the pants.

As I have previously mentioned, I have a problem with Equipment tops and button downs. This is the first one I ever owned. I bought it on sale at a store in Kansas City last spring.  This was before anyone in the Midwest knew what they were and I reaped the benefits (it was $70 and I was the only one who owned one at the time - I am still kicking myself for not buying seven more). I also have to make an announcement: Theyskens’ Theory knows how to make work shit look cool. This is a little mullet sweater vest that I wear year round. Sometimes (if I get a little crazy) I wear it without a shirt under it.

I usually opt for heels, but last week I broke in some new 5 inchers and, quite honestly, my feet are bandaged and should not be on public display. I do posses a higher level of personal discretion, you should thank me. Flats are totally cool to wear, just please, don’t wear your Nikes with that pantsuit. Dear God! There are zero reasons for that (that goes for you too men of the city). I have these old Dolce Vita loafer things that are basically real life slippers and I kick it in these all around town. You should get some.  They rock. Mine are actually about to fall apart but God help me if I won’t see them through until the end. For better or for worse.

New grads, don’t let your office become a gateway to poor dressing and falling off the bandwagon. You are young, you are fun, and you can still shotgun a PBR like a champ at that office summer BBQ!

Pictures from mi amigo Mr. Justin Livingston