Gossip Girl Outfits That'll Keep You Warm All Winter

By Holly Glasser··  5 min read
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If you're anything like me, you love dressing up for winter. It can be a challenge to always look cute while working against the cold; however, I'm here to help you stay bundled up and cozy, as well as polished and posh.

I've turned to none other than Serena and Blair of Gossip Girl to find some inspiration for your winter wardrobe. These girls have it down to a fine art - always carrying a bag, wearing interesting shoes, and sporting other fun accessories such as a hat or scarf to tie their look together. Indeed, both Serena and Blair are sure to delight us with accessorized outfits by mixing patterns, colors, and textures.

Below, I have shared my three favorite winter looks from both Serena and Blair. Almost every look can be purchased at a store near you or online for around $200 or less for the entire ensemble. Of course, having designer coats and bags and shoes like Blair and Serena is not always an option, so I've gone on a scavenger hunt to find similar wardrobe pieces that may have a different label or fabric, but still result in the same look.

Have fun gleaning new insight into fabulous and affordable winter-wear, thanks to the inspiration of our beloved Gossip Girl heroines of the Upper East Side!


Here, Serena wears a gray shearling cape by Ralph Lauren Black Label, with a thigh-high mini skirt, gold and brown bag, and brown booties.


Photo Credit: The CW via PA Images

I've found the look with more affordable pieces in the following places:

  • Cape/Poncho -Shein-$24

  • Knitted Skirt - Meshki- $18

  • Brown Shooties - TB Dress- $69

  • Tights - Macy's- $14.00

  • Purse: Search for a thrifted gold bag on Poshmark in brands like Kate Spade and Coach ($40 - $80 price range)

Blair, who is known for wearing citrus hues, sports an adorable bright green cape here with a neon yellow bag, a polka dot scarf, and gray gloves.

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Photo Credit: Rex Features

How you can recreate this look:

Casual Chic

Here, Serena sports a gray coat with off-white cowl neck sweater and knee-high boots.


Photo Credit: The CW via Doug Meszler / Splash News

It's an effortlessly casual chic look that you can easily recreate at the following retail stores:

  • Sweater - H&M - $34.99

  • Coat - ASOS - $89

  • Tartan Tights - Target - $10

  • Cashmere Gloves - Net-A-Porter - $70 (A little splurge here, but treat yourself!)

  • Thigh-High Boots - Shein- $31

  • Purse - Search for a tan-colored bag on Poshmark in brands like Kate Spade and Coach ($40-$80 price range)

Serena looks striking in this effortlessly posh look, and you can look the same by adding just a few staples to your wardrobe.

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Photo Credit: Rex Features

Recreate this look at the following retailers:

  • Black Trench Coat -Shein -$19

  • Sapphire Blue Scarf - Hippirhino - $15.50

  • Black Gloves - ASOS - $31

  • Black Leggings - H&M - $9.99

  • Black Knee-High Stiletto-Heeled Boots - Shein - $33

  • Purse - Search for a brown-colored bag on Poshmark in brands like Kate Spade and Coach ($40-$80 price range)

Classy and Feminine

Here, Blair wears a very ladylike ensemble in classic colors.


Photo Credit: The CW via Rex Features

You will be delighted to find that the retail stores below will easily allow you to recreate this look on a budget:

  • Navy Blue Double-Breasted Coat - Shein - $26

  • Navy Pointed Toe Flats with Buckle - Shein - $17

  • Purse - Search for a red-colored bag on Poshmark in brands like Kate Spade and Coach ($40-$80 price range)

I have to finish with my favorite look: It's so dainty and charming, so girly, while also being so fresh, demure, and tasteful. It screams "fun" and "classy" all at once! I can't stop gushing about this look.

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Photo Credit: Rex Features

To me, this ensemble is a real gem, and it's so easy to recreate on a budget:

  • Gray Poncho - Shein - $21

  • Yellow Beret - Wish - $2

  • Mustard Yellow Blouse With Sash - Stylesimo - $17.99

  • A-line Gold Mini Skirt - Ali Express - $21.53

  • Fishnet Stockings - Shein - $2

  • Burgundy Mary Jane Shoe - Modcloth - $45

  • Purse - Search for a yellow-colored bag on Poshmark in brands like Kate Spade and Coach ($40-$80 price range)

Well, there you have it - six fabulous and affordable looks from Serena and Blair to style yourself from head-to-toe this winter like an Upper East Side girl with classic yet affordable wardrobe pieces that will satisfy season after season! If you're on a really really tight budget this winter, I suggest getting a few staple pieces, such as a couple berets in different colors, a few different textures in hosiery, one or two really brightly colored scarves, a plush sweater, and a pair of gloves. You can make do with one really nice pair of boots and a versatile coat. You can mix and match these staples with pieces already in your closet.

Closing Thoughts

To get the best deals remember to take advantage of holiday sales, subscribe to your favorite fashion stores to stay up-to-date with deals and coupons, and utilize marketplaces like Poshmark and Depop. You can even have a wardrobe exchange party with friends. Check out your local thrift stores, as well. You’re bound to find some hidden treasures along the way. Happy Wardrobe Refreshing!

*Updated 6/11/2020

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