41. Working Girl Via style.mtv.com Blair makes her debut as the head of Eleanor Waldorf Designs. She looks radiant in her RED Valentino dress and Brian Atwood pumps. Her feminine updo perfectly complements the look. 40. Modern and Chic Via blairfashion.blogspot.com Blair wears an uncharacteristically modern dress from Victoria Beckham's Spring 2010 collection for Yom Kippur dinner. 39. Sixties Chic Via blairfashion.blogspot.com Blair wears a Thread Social mini dress in the first season. She daringly pairs black tights with a white dress and the results are perfection. 38. Making a Deal With the Devil Blair wears this stunning Matthew Williamson gown, when she goes to secure Chuck the Empire Hotel. 37. Classic & Chic Via liveinfashion.wordpress.com Blair looks timeless in a trench coat and Louis Vuitton bag. 36. Poolside Perfection Via blairfashion.blogspot.com The vintage silhouette and bright colors of Blair's Salvatore Ferregamo one piece make it an iconic look. 35. Get Nauti Via donafilo.wordpress.com Blair looks adorable in her retro Bettie Page dress with a modern neckline. 34. Eleanor Waldorf Design Via blairfashion.blogspot.com Blair models an Eleanor Waldorf original, which is actually by ghost designer Abigail Lorick. 33. Houndstooth and Pink Blair visits Lily in an Alexander Wang blouse, Brooks Brothers skirt, Escada coat, Valentino bag, and Lanvin shoes. 32. Solid Separates Via blairfashion.blogspot.com No one does skirt blouse combos quite like Blair. In one of her most successful looks, she wears a Marc by Marc Jacobs skirt, Yaya Aflalo top, and a Nancy Gonzalez clutch. 31. Statement Piece Blair's Alexis Mabille gown is a work of art. 30. Blair Golightly Blair channels Audrey Hepburn in Breakfast at Tiffany's in her Burberry trench. 29. Stripes on the Met Steps Via blairfashion.blogspot.com Blair make a colorful statement in a Co-operative designs sweater dress with Elizabeth and James heels and an Alex Bittar cuff. 28. Princess Bride Blair marries Louis in Vera Wang. 27. Print Perfect Blair looks flawless under her clear plastic umbrella. Her mixed prints look great with the bright blue bag. 26. Quintessential Blair Via blairfashion.blogspot.com Blair wears a Milly coat over a Fendi dress and carries a Louis Vuitton purse. 25. Fresh Squeezed Via blairfashion.blogspot.com Blair looks amazing in citrus hues. Skirt from Stella McCartney Spring 2011. Riki Rosetta bag. 24. All In Via blairfashion.blogspot.com Blair follows Chuck to Monte Carlo, where she surprises him in this stunning dress. 23. HBIC Via blairfashion.blogspot.com Blair is back in full force in this Reem Acra Fall 2011 gown and Giuseppe Zanotti heels. 22. Blair takes France Blair embraces French fashion in her Moschino frock and Chanel bag. 21. Lady in Red Via blairfashion.blogspot.com Blair's dress is from Victoria Beckham Fall 2009 and her headband is by Paige Gamble. 20. Meet me at the top of the Empire State Blair goes to meet Chuck at the top of the Empire State Building. She accessorizes her green cape with a bright Longchamp bag. 19. Damsel in Dior Via blairfashion.blogspot.com Blair wore this Dior confection to her bridal shower. 18. Park Avenue Princess Via blairfashion.blogspot.com In one of her most over the top looks, Blair wears an Alberta Ferretti dress with a Moschino jacket and Marc Jacobs handbag. 17. How do you feel about me? Via blairfashion.blogspot.com When Blair asks Chuck how he feels about her dress, he replies: "I adore it." But when Blair asks how he feels about her, he can't summon he words. In this scene Blair wears a Philosophy di Alberta Ferretti Fall 2008 dress with a Simon Tu necklace and Jennifer Behr headband 16. Ruffles for Days Via blairfashion.blogspot.com Only Blair could make this Bill Blass top work. 15. Princess for a Day Via blairfashion.blogspot.com Blair plays dress up in an Oscar de la Renta Resort 2012 gown. 14. Blair's Cinderella moment Via usmagazine.com When Blair meets Prince Louis at the Louvre, it seems like she's found her Prince Charming. She looks beautiful in her Bensomi dress and with her missing Roger Vivier pump, she pulls off the Cinderella look like a real princess. 13. Vintage B Via blairfashion.blogspot.com A young Blair pairs a Trina Turk cape and a Marc by Marc Jacobs dress with her signature pattern tights. 12. NY Prep The blazer and headband make this an early iconic look for Blair. 11. Pretty in Pink Via usmagazine.com Blair chose a Collette Dinnigan dress for Rufus and Lily's nuptials. 10. Princess Material Blair meets Prince Louis's mother in this sparkling Jenny Packham gown. 9. An American girl in Paris Blair looks like Parisian perfection in head to toe Chanel. 8. Retail Therapy Via blairfashion.blogspot.com Blair does Paris shopping right in a Maxine Simoens couture dress and Louboutins. 7. Easy Rider Via blairfashion.blogspot.com Blair perfectly complements her cruiser with an adorable Alice + Olivia dress and Lulu Guinness flats. 6. Constance Queen Via blairfashion.blogspot.com Blair wears a Rag and Bone jacket and a Foley and Corrina bag. 5. Prom Queen Via usmagazine.com Blair wore a one of a kind Marchesa gown to her prom. 4. I Love You, Blair Waldorf Via blairfashion.blogspot.com Who could forget what Blair is wearing when Chuck finally says I love you. Nanette Lepore coat, Pour La Victoire shoes, Jennifer Behr headband, and a Stuart Weitzman bag. 3. Forget Paris Blair and Chuck come face to face in Paris and Blair wears a gorgeous Oscar de la Renta gown. 2. White Hot Via blairfashion.blogspot.com Blair wears one of her most iconic looks to a white party on the Hamptons. Her dress is Marc by Marc Jacobs and her shoes are Chloe. 1. Something Blue Via blairfashion.blogspot.com Blair becomes Mrs. Chuck Bass in this Elie Saab Spring 2012 Couture gown and Jennifer Behr headband.