What Jessica Christopher Day Wore in Portland

Wedding bells are ringing for Jess’s Dad and his fiancee, Ashley, so the group sets out for the rainy, hipstery hamlet of Portland, Oregon. In the midst of her Best Man duties, Jess (middle name Christopher, apparently) muddles through the struggles of a long distance relationship with Ryan. The time difference proves to be the least of their problems (though Nick stepping on Jess during her nocturnal phone dates isn’t the greatest) when Ryan decides to cancel his jaunt to the West Coast. Bummer. Winston’s still hung up on the whole Cece Hearts Schmidt thing, and it looks like Cece might just hop on that bandwagon…despite a gloriously built, tousle-haired firefighter. Oh, and Coach tried to be a hipster because I have no idea. When in Rome, I guess?


Everyone’s ready to head up to Portland to support Jess at her dad’s wedding, and for their foray to the Pacific Northwest the guys have gussied up in their usual fare. Schmidt has his sweater and button-up combo which looks nice and warm (don’t mind me, it’s like 2 degrees outside so I’m drawn to layers right now) and perfect for a day of travels. 

I would say that Nick knows his destination’s audience, but let’s face it — the man lives and breathes plaid. This particular specimen, however, is clearly not from the bottom of the barrel. The bold lines are much more flattering than…well, everything else he has. Coach, on the other hand, has some strange inverted color scheme going on with his two-piece and regretfully (or not, depending on your mood) Winston is without a wildly patterned shirt. 

The girls’ travelwear is just as all over the place as the guys’. Jess must really be feeling the strain of Ryan’s return to England and must be trying to mask her pain with those bizarre ruffles. This Harvey Faircloth fancy sweatshirt top is not doing our Jess any favors — the ruffle and the collar are fighting each other and what the hell is going on with that hem? I mean, I get the whole fancy-casual, fashion-meets-tee-shirt-material thing, but at the same time I really just don’t. 

Cece, of course, has got it together. Well, until she learns that her girlhood crush, Jake Apex, will be at the wedding. Then, it’s all incoherent gibberish and brief blackout spells. But in the meantime, she looks casual and comfortable, yet smart and edgy in her blouse and Lucky Brand leather jacket duo. That is not a color I’m generally fond of but I might now have to reconsider… 


Cece continues her love affair with all things blouse-y with this turquoise blue dress she chose for the rehearsal dinner/Jake Apex Reunion #1. It’s hard to go wrong when you put her in a plunging neckline. 


Unfortunately, the same can’t be said for Jess, whose wardrobe clearly took a backseat in this episode. I can’t say that this particular Trashy Diva halter dress flatters her cleave so much as it just puts it out there. The fit, the tropical-esque pattern, the random black cardigan, and the pony are just so retro. Maybe she’s going to pick up a few hours at a local tiki bar?

I will cut the girl some slack, though. It’s got to be hugely disappointing to learn (and at the last minute! harumph) that your boyfriend won’t be hopping the pond to join you and meet your family. Which, might I add, she had done for him. But, whatever. I’m not bitter about it. 


At least the guys who did show up for her stepped up their sartorial game. Mostly. I don’t even know why I thought plaid wouldn’t be an option for Nick, but the blazer is much appreciated. As is Winston’s gray and white damask shirt. Sometimes, it’s okay to boldly go where few have gone before. Carry on, Winston. 


Both Schmidt and Coach opted to go classic and stick to dark color palettes. It’s fine. It’s appropriate. It’s also boring, but Coach must’ve been too busy Yelping the best Portland hotspots and Schmidt too distracted by his girlfriend Fawn’s hairlessness to bother packing something more interesting.


In an effort to cheer up Jess, Nick volunteers the group to go on Jess’s elaborately orchestrated tour down memory lane. If I didn’t previously think that Nick secretly still loves Jess, I do now. It must really still be a secret because he’s not even dressing to impress. Winston looks casually dapper in his charcoal peacoat and I’m really excited about that crazy patterned sweater I see peeping out. 

Cece is effortlessly stylish as usually and OF COURSE the rain hasn’t ruined her perfectly straight coif. Also, please notice how her scarf and overcoat are colorblock twinsies. AND how Coach isn’t wearing a track suit. Are those jeans? Is that a henley underneath a real jacket? Is he LAYERING? And because that isn’t enough, Schmidt is all about that sherpa collar. Mmm, cozy. 


Despite the previous night’s heartbreak, Jess looks pretty as a peach, if not a little demon-eyed, in her tried-and-true navy peacoat and that charming neon yellow umbrella. How are her bangs not even a little messed up from this rain? Don’t cry, Jess. Even if your boyfriend isn’t there for you, your perfect hair will never fail you. 


It goes without saying that it is beyond sweet that everyone would go on Jess’s Portland tour just to cheer her up. And it was going great until the Union Jack exploded all over Jess’s mom’s house. 

Mama Day falls apart when she realizes her proxy Prince William will not be joining them, which means Jess falls apart, locks herself in her room, and laments not ever having the chance to find real love with Jordan Catalano. 


Nick continues to pick up the pieces of her broken heart and before you know it, it’s the wedding day! Jess completely forgets about Ryan when she realizes that she forgot Papa Day and Ashley’s wedding rings at her mother’s house. Which is sort of good, because it probably took her mind off this Colonel Sanders/Wednesday Addams love child outfit.


Haven’t Jennifer Aniston, Solange, and J.Lo taught us everything we need to know about fabulous lady suits? That ridiculous neckpiece was absolutely not on the syllabus. 


With Jess occupied with Papa Day and his man-corset, Nick and Coach are charged with retrieving the rings and make haste in these suits. Nick looks about as good as he can, but would it kill him to wear a tie? And is Coach for real??


Horrible decision-making at its finest but I guess the tracksuit turned out to be a stroke of luck, seeing as how their search led them straight into Joan and Co.’s acid trip/group dance orgy. 


Back at the wedding, Winston is a shining example of everything business casual aspires to be. Are we sure he went to the Police Academy and not Parsons School of Design? The spot-on tailoring, the subtley patterned shirt, the full-on buttoning up in lieu of a tie? You don’t just pick up a good eye for menswear off the street.

Never mind, that’s completely false and you totally can.


Either way, he totally called it with Cece. After Schmidt’s brief campaign to hook up Cece with Jake and a heartfelt promise to always try to make her happy, it was all over for her. Too bad Schmidt’s still with the councilwoman, because how cute are these two? Even though I’m like an inch away from being completely over her penchant for blousey, v-neck items, it’s hard not to fault her in this Elizabeth and James magenta number. Don’t they make one knockout couple?


Now, what’s a wedding without a wedding dress? The new Mrs. Ashley Day is lovely in her dress. Ignore her face, she just found out Jess doesn’t have the rings. 

But while Ashley got her happily ever after, sadly, Jess didn’t. Accepting that she couldn’t spend the rest of her life thinking that her phone was buzzing with his calls, and that she needed someone who could be present in her life (cough, like Nick, cough cough), she broke it off with Ryan. Lucky for her, she’s got five incredible friends to comfort her. And hello, it’s a wedding — I hope someone got her to that open bar.