Winner #1: From the episode "Bonfire of the Vanity" 3 weeks ago. It may not look like much but blow it up and pay attention to the detail. The matching blue pocket square. The fine stitching of the plaid jacket. The deep blue sweater vest beneath. And I know you can't see them, but the elbows are furnished with dark brown patches. Nice.
Winner #2: Neither of Chuck's outfits in "The Magnificent Archibald" were all that spectacular; just your usual tie (red), vest (tan), and geisha-like smoking jacket (navy). So let's focus on the scene surrounding this bathrobe, shall we? Yes, that's Chuck having a martini-toast with the woman who has just shaved his face in his own private barber shop. Jacob's recap says it all:
"Eric's mind is so fucking blown that it propels him up the stairs and into Chuck's room, where he's delighted to see Chuck is home. And here's what Chuck's up to right now: getting a shave and facial from a silent woman in a French maid costume, while they drink martinis together, wearing a smoking jacket. "My plans for the evening got held up at Customs," he smarms, but I think these "plans" are imaginary as I often do, because he's got an image to protect. Eric must not know that he is impotent, because he loves Eric the most of anybody besides Nate, who I guess also must not know about the mechanical errors, so: "plans." Eric's like, "YOUR DAD TOTALLY JUST BLEW MY WHOLE MIND" and Chuck's like, "You know I have a PI on retainer -- you think Bart wouldn't?" He clinks martinis with the French maid lady at this point. He is like twice as Chuck Bass right now as usual, it's awesome. Eric's like, "Isn't that totally fucking fucked up, though? Am I wrong here?" Chuck, because why would he know better, is like, "I don't even know what fucked up means. It's what we do. Remind me to tell you about the time I found these amazing surveillance photos of Gina, my hot Italian au pair who later molested me and contributed to the insane mess I am!" Eric takes a pass on that one, and Chuck offers him the keys to the vault. And because it's Gossip Girl, yes: there is literally a vault, with literal bars of gold in it."
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