Drew Barrymore looked quite chic for her visit to The Late Show with David Letterman. She veered away from her bohemian style, going for a more elegant, yet totally hip look. A sequined top, black pants, and YSL pumps will get you there in no time.

Miss Bilson looked stylish and cool in basics for some Beverly Hills shopping. Jean shorts are such an easy Summer throw-on. Pair yours with wedges (like Rachel’s Rag & Bone pair) and a cut-off sweatshirt for a similar chic, casual look.

Nanette Lepore printed dress? Check. Nancy Gonzalez croc bag? Check. Tiffany Key pendant necklace? Check. Get Leighton Meester’s (Blair Waldorf’s) entire look right here. The flip-flops were only for between shoots, so we’d go with a patent pump or a great flat sandal for day.

This DVF dress is a perfect day-to-night piece. Kim wore hers with Christian Louboutin suede boots, but it would also look adorable with strappy flat sandals in the day, or sexy high heels at night. Belt it like Miss Kardashian, or leave it plain and simple.

Leighton Meester looked cute in her olive cargo pants and cream accessories on the Gossip Girl set in NYC. Her look was casual and low-key, but black wedges and cat-eye sunglasses added some extra sophistication.

Rachel Bilson threw together a super cute daytime look for some errands in LA. Her floral skirt and white top looked great with a jean jacket, and Rag & Bone booties made it stand out even more.

Sarah Jessica Parker has, once again, succeeded in creating an effortlessly chic ensemble. For a screening of The Big C in the Hamptons, the ever stylish actress opted for a Donna Karan jacket, which she kept casual with a simple gray dress and flat sandals. Easy to wear, and easy to re-create.

Accessories definitely made Bilson’s daytime look. Her jeans and black top were simple, but a Sunshine & Shadow colorful belt, See by Chloe clogs, and cool patent shoulder bag made for an outfit to remember. Simply stylish, Rachel.