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Fantastically flattering wrap dress

How about, for example, a warm cardigan over the dress (also available with rhinestones, for example from The Seamstress of Bloomsbury via Etsy*) or a thin turtleneck sweater under the dress

If You're Spending $500$1,200 Suit: Suitsupply linen-wool blend, half-canvassed ($600) Shirt: Proper Cloth made-to-measure ($150) Tie: Drake's silk grenadine ($150) Shoes: Allen Edmonds Strand in walnut ($425) If Budget Isn't the Issue You don't need my advice

Orange Floral Babydoll Dress

Below you'll find both Meester now and on set way back when, proving definitively that Blair Waldorf would be all over this dress in 2018

Virtual Try-On Assurance: The fitted bodice and flowing skirt balance structure and gracerefer to our size chart for precise measurements