Fresh from her defeat at the hands of Blair and the Mean Girls, Jenny is grounded in Brooklyn, but even Rufus’ punishment can’t keep her down for long.

For school one morning, Jenny chooses this ensemble, guaranteed to keep her on the outs for even longer.  The snapped crossed tie is just plain ugly, especially paired with the overly-ruffled blouse.  The jumper is cute though, and I do like her blue coat.  Also, this was my favorite period of Jenny hair.  The swept bangs with the curled chunks around her face are so flattering.  I wish she’d kept it short like this longer.


Jenny spends much of the school days during this episode in very similar outfits—the only girl at Constance Billard who is apparently required to wear anything resembling a uniform.

My favorite version is this one:

The purple patterned scarf is so lovely with her skin tone, and contrasts beautifully with the dark somber fabrics of her jumper and coat.  Plus, the patchwork tapestry bag is a fun, nearly boho touch.

Plus, has Jenny ever looked this sophisticated?  Nope, and she never does again.  This is an unfortunate short-lived detour.


Grounded at home and annoyed she can’t launch her new plan to rule Constance, Jenny wears a simple top and jeans.

I think we might have seen this in a previous episode (if we have, brava, Eric Daman and co.), but I love the purple and the square neckline is beautiful on her.  Plus, I have to give props again for the great hair, and continue mourning that it didn’t last.


Finally, Jenny manages to outsmart Rufus and engineer a date with the new plan named Asher.  After all, as Jenny points out to the new minion, even Blair doesn’t have a man right now.  Nobody does.  Except for her, of course.

For the date, Jenny wears this simple sundress with a flowered pattern and color-blocked bodice.  I don’t like the light pink against her skin (it’s too light), especially when it’s paired with such a bold choice as the cerise belt.  Still, she looks young and cute and sweet, which is probably exactly the impression she wanted to make.  After all, most boys aren’t interested in dating a human piranha.


Asher, Jenny’s new “plan,” looks like most young teenage boys on the Upper East Side, but apparently he’s supposed to be dreamy in that young Nate Archibald lookalike way.

He certainly has the Nate Archibald look down with his plaid button-up shirt and jeans—but I do think the black wool coat has some interesting detailing like the hood and the toggle buttons.


For the date, he doesn’t vary it much, but then why should he?  He already knows he’s exactly what Jenny wants.

Though he couldn’t possibly know that even though Jenny Humphrey appreciates a Nate Archibald sweeping bang haircut as much as the next girl, she wouldn’t like the combination of so many distracting plaids.  After all, she’s a Humphrey and therefore an expert on plaid.


Speaking of plaid, let’s check in with the head disciplinarian himself, Rufus.

What Rufus?  No plaid this episode?  Is it even possible?  I’m in shock too.

To make up for his lack of plaid, Rufus does bring back the awesomeness that is the Nehru collar.  Unlike fellow YKYLF staffer Bella, I can’t say I like a man in a Nehru collar.  They always look strangely abbreviated to me, like someone forgot to sew the rest of the shirt on.


Later, he chooses this bizarre ensemble.

Jean shirts are just a big no-no, and especially paired with a Henley the color of well . . .nothing.  Of all the shirts Rufus has ever worn, that’s the most blah and colorless we’ve seen on him  yet.  I hate to say it, but considering the above fail, I almost missed the plaid this episode.