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Take a Ride on the Hot Mess Express: Our Most Unfortunate Workwear Ensambles

Let’s face it, although social media would have us believe otherwise, none of us live Pinterest perfect lives.  Hell, we can’t even pretend too.  With that in mind, we thought it would be fun to share some of the worst things we’ve ever worn to work as actual adults who should have known better.   

Katie 1: Besides taking the interview attire advice offered by my law school career services office too literally (because we ALL did that), I would have to say that the most cringe-worthy workwear mistake I’ve made involves a really lovely Banana Republic suit that I bought at the Salvation Army.  Said suit was in my size but a Tall. I’m 5’4”.  Clearly this required pretty extensive alterations that I naively thought my dry cleaner could handle.  I. Was. So. Wrong. Oh good lord was I wrong. The alterations were a disaster, especially the shortening of the sleeves on the jacket.  That was the worst.  Not only were the alterations a disaster but I convinced myself that they looked fine and wore the suit anyway for at least 6 months of my first year of practice.  Thankfully my first 6 months of practice didn’t involve a lot of court appearances. 

Elizabeth:  Most of my unfortunate choices seem to be outfits that looked acceptable in the mirror at home and then mysteriously in the office the neckline or hemline suddenly became more risqué than I would be comfortable wearing in the office.  Occasionally, I would realize a blouse was actually somewhat see-through.  Most of these issues could be remedied with a camisole, and so a lunch trip to the Loft did the trick.  However, I do recall one occasion when I spent the entire day with a scarf on to cover my décolletage.  A winter scarf. 

Katie 2: So I always make wonderful choices when it comes to my workwear. My biggest problem is that I never (read NEVER) check the weather before I leave the house. So while my light blue flared A-line skirt and white button down looked flawless, it was very flawed while standing on the corner waiting to cross the street at lunch and a giant gust of wind came up, lifting my skirt and showing my (admitted cute but not for public viewing) undies to the whole of the Chicago Loop out for lunch.

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