Best and Worst Fashion From Gossip Girl Season 4, Episode 16: “While You Weren’t Sleeping”

Relationships aren’t the most solid foundations on which to stand when you’re on the Upper East Side. That being said, there were still some new ones forged while old ones were reinforced in Episode 4.16, “While You Weren’t Sleeping.” But whether you’re making a new friend or trying to intimidate an enemy, fashion can play a big role, as it did for a bunch of our favorite gossip girls. Let’s find out who played their sartorial parts with flair and who simply couldn’t pull it off.

Hot: Lily as the Lady in Red

Even though Lily is always trying to put her wild past behind her, she sure knows how to attract all sorts of attention from the wrong sources. Dressing herself up in a figure-skimming red dress — but not of the skintight variety that Serena loves to sport — was all she needed to do to send Russell Thorpe running.

Hot: Eric Comes of Age

Now that Eric is becoming a man, it only makes sense that he should grow into a serious wardrobe. Considering that he already looks more put-together than Dan usually does, he’s off to a great start.

Blair’s Major Oversight

It’s not that this isn’t a perfectly lovely outfit, but sometimes fashion does boil down to a simple formula — one that usually requires matching shoes (unless you’re Helena Bonham Carter, of course).

Serena’s Casual Corner Style

The magpie tendency went off the rails for Serena, resulting in a cowl neck that’s so massive it manages to show off skin, set atop a strip of embellishments that wrap around her waist.