White on White.

Sweater: J.crew (old, but similar here)  |  Shorts: J.Crew

Sunglasses: Ray Ban  |  Bracelet: Tiffany & Co. (similar here)

Maxed Out

Top: Lilly Pulitzer (folded under)  |  Skirt: Sabine  |  Shoes: Jack Rogers

Bag: Louis Vuitton  |  Sunglasses: Chanel  |  Jewelry: David Yurman, Tiffany & Co, Olive Yew

Orange and Monograms

Bikini Top: J.Crew (old, but similar here)  |  Pants: Lilly Pulitzer  (similar here)

Hat: Marley Lilly c/o  |  Necklace: Olive Yew

Seacrest.

Dress: Gretchen Scott Designs | Shoes: Jack Rogers (similar here) | Sunglasses: Chanel

Belt: J.Crew (similar here) | Bangle Watch: Kate Spade

Ahoy!

Top: Jack Wills (similar here)  |  Skirt: J.Crew (old)  |  Hat: Smathers & Branson

Bag: Sea Bags (crab version here)  |  Bracelet: Tiffany & Co. (similar here)