Hey Upper East Siders!

Netflix’s Gossip Girl is back home for the holiday season, and so is a flood of opinions on the outfits of Serena Van Der Woodson and Blaire Waldorf. These New York City socialites have a style that’s aged like fine wine, but anything, especially a look from the early 2000’s era, can always be improved with a few modern accessories. We’ve taken some of Blair and Serena’s most iconic ensembles and paired them with a few items we think should have been a part of their most memorable looks.

Oh and of course, a timeless outfit from the show that should never change. After all, we’re here for an honest fashion show review, not to get on Blair’s bad side!

Xoxo, Keep Reading!

There’s nothing like a Gossip Girl Thanksgiving season. One of our favorite looks that’s almost perfect is Blair’s “casual fall dress on an everyday outing with Dorota. Her periwinkle cape coat over a dark emerald dress is a beautiful cool toned contrast with her fall toned vintage Isabella Adams drawstring handbag. The only way to make this look more timeless and season-appropriate is to accentuate the chocolate brown color and golden accents of her accessory with a minimalistic and posh belt, one that’s the exact size of her brown marked waistline. To make the outfit more maximalist chic and trendy, adding layering with an accessory like this fall color scheme skinny 3 piece leather belt and chain set is a perfect choice. Top it all off with a chic gold plated band, and a motivational phrase that encompasses Queen B’s character with this “Goal Digger” customized bracelet, and she’s more golden than she already is!

The golden girl. Literally! Like always, Serena Van Der Woodsen goes for subtle glamour, which you can spot in her brass gold studded cuff bracelet, an unusually edgy addition to an otherwise posh and mature luxury outfit during season 3’s Last Tango, Then Paris episode. This unforgettable fitted cocktail dress, platform heels, and statement necklace immediately reminded us of the Lizzy Crossbody, a gold accent purple toned lizard print piece that would beautifully pair with the muted purple and grey tones of Serena’s iconic outfit. For less chic, more play, we’d opt for some more studded cuffs, alongside the Puppy Scrunch sequin bag, for its designer-like silhouette and added dimensions.  Some architectural brass cuff earrings never hurt either!

When Jenny first appeared during this episode on screen in season 2, we almost gasped. How could Gossip Girl’s queen of high goth be missing her maximalism? It never hurts to experiment but a few ways we know Jenny’s look would live up to her own ambitions would be to add a grunge studded statement belt to block up the flannel dress, and a baguette handbag that coordinates. We know Queen B’s successor wears jewelry like no other, standing out from the Upper East side crowd with her layered necklaces, smokey eyes, loose neck tie, and bangle bracelets. With some more silver accents and some layering, this 2014 tumblr look would age beautifully for today!

The title says it all. And to really channel Blair, you have to look the part. One way her corporate inspired, no-nonsense ensemble could get even better is by accentuating the chain accent on her bag by matching it to a waistchain. What better waistchain than one that ALSO creates a common theme with her brooch? Matching the hardware and the shapes within her fit emanates power, intention, and coordination. If the chain belt youthens the ensemble too much, we’d pair her power suit and skirt combo with a statement pendant lioness leather belt, or a golden buckle black sash. 

Ah, the early days. Before her dark style turn of Gossip Girl’s season 2, Jenny Humphrey was just an eager high school freshman looking to fit in with the It Girls of Constance Prep. But you can still see her fashionista shining through, especially here, where she plays with the drama of wearing colors on the opposite side of the spectrum at once. We hate to change such a successful experiment, but this look may not do as well today as it did in the early 2000s. To improve its generational appeal, we’ve matched her pop-of-color top and bow kitten heels to a matching mini bow baguette with a chain handle and a skinny leather belt with an upper class inspired rhinestone buckle. Each is a new accessory inspired by the higher end designs her idols were wearing at the time!

Oh, we’ve got the perfect bag for this. Nothing says meant to be like a pair of matching boots and sling bag. Jenny Humphrey’s gothic style left a mark on every Gossip Girl fashion lover, and what better way to leave an impression then with an oversized pewter shimmer bag that perfectly accentuates her pewter knee-high- slouch boots from season 4? The bracelets are, well, an obvious choice if you’ve ever seen Jenny-centric episodes.

Vanessa may not be everyone’s favorite gossip girl, but you can’t deny the beauty of her all silver evening ensemble during the snowflake ball. Her one shoulder sheer sparkly toga and matching grey cloak gave her a greek goddess look that can only be improved upon with an equally sparkling clutch case. This elongated rectangle shaped evening clutch in silver, adorned with three dimensional rhinestones perfectly compliments the sheer shimmer fabric and rhinestone silver hoops Vanessa chose to wear to the snowflake ball. Pair her East West clutch, her toga style gown and cloak with a few bangle bracelets to compliment her hoops, and Gossip Girl has another high end outfit to add to the show’s ranks. The best silver bangles we can think of are a silver engraved leaf wrap around style with an elevated marble stone embellishment, along with an adjustable accent bracelet titled “No Regrets”, true to Vanessa's character.

Nothing says reconciliation (for the 100th time) like a matching duo outfit after reuniting with your best friend. Everything, and I mean everything, down to the thin belt, the hair, the capped sleeves and the open back is too iconic to change. It’s an everyday look, a Halloween costume with your bestie, and brunch outfit in one!