What Jess Wore

Jess’s triumphant return to teaching goes awry when Nick gets it into his head that one of her students, Edgar, is a big ol’ bundle of crazy. So, as her fearless protector, he joins Jess’s class to keep an eye on her (cue the “awwws”) and adopts the absolute best character: Julius Pepperwood – who else was shuffling with excitement at all da Chi-town references in this episode? And speaking of wood, Winston sure knows how accessorize his morning kit. But, anyway, the crazy erupts when Jess and Nick think Edgar wants to kill Jess – Nick gets conked on the head, Jess gets pepper sprayed, Edgar turns out to be a super nice guy with some strange habits, and they meet the ultimate cougar. Cougars and bunnies (you’ll see) and Bears, oh my!


Jess is your quintessential schoolteacher in this very winter-palette friendly combo. Other than Emma Pilsbury, I don’t know who else can shimmy into this high-necked Orla Kiely blouse with gold collar detail and not look like a total prude. The a-line black skirt and the belted waist turn this look from dated to vintage (read: old and ugly vs. old and cute). A+, Jess.




Er, is she teaching an adult writing class or a tennis workshop? While the pleated magenta skirt is a welcomed zing of color, the white blouse is blah – the color’s boring, the fit is sloppy, and where are your accessories, Jess? Other than the “Hot for TEA-cher” mug that I kind of want, she needs to go home and finish getting dressed.


This Eva Franco dress, on the other hand, definitely gets a gold star. Probably fifty gold stars. The cobalt blue is such a vibrant, beautiful color on her, the bow at the belt is so feminine, and the doll print is just gosh darn fun and whimsical. The pleats of the skirt add a bit of body to the silhouette, and the colorblocked blue hemline is a great touch and pulls the whole dress together – like bookends, if you will. Throw in a sweet little heart-shaped purse and well, that’s just darling. 


Hey, where’d all the pleats go? In any case, Jess’s mint green cable knit sweater looks super cozy and good thing, too. Might as well be comfy as you embark on the most uncomfortable pogo-centric conversation with your roomies. 


As stunning as she was in the blue dress, red has to be her best color. But, her best accessory? Clearly the bunny phone case.  The red bunny phone case.  


I want to like this look, I really do. There’s a bow belt involved so every part of me is fighting to like this, but I can’t. The dress is perfectly vintage and fabulous, I’m sure, but that purple cardigan just makes the whole thing so awkward. It’s as if the sweater sucked all of the volume from Jess’s glorious hair to create this weird billowing effect around her waist. She needs to put down that mug that’s not as cool as the first one and either take off that sweater or wrap her belt around it.  And then maybe we’ll like it.  

So, class, what have we learned this week? Chicago is awesome, novelty accessories are always a good idea, and pleated skirts are the end all be all.