Gwyneth does casual chic in her Hamptons-ready outfit, donning nautical stripes and a pair of basic black shorts. I love how pulled together she looks even when this dressed down.

Gwyneth masterfully reworks the classic little black dress, pairing it with sky-high tough gladiator sandals and a black satin clutch. Her jewelry is kept relatively minimal aside from a couple edgy statement pieces, allowing her to achieve this pared down but still very different look.

Gwyneth goes for the drape in this asymmetrical white beauty, intensifying the look with the strappiest gladiator heels around. The Grecian look goes in and out of style so often that it’s essentially a classic, and if done right, will always look right. Her diamond cuffs and skinny patent clutch finish this off sleekly, leaving Gwyneth looking the goddess she is.

Gwyneth is the epitome of airport chic in this comfortable but still pulled together ensemble. Her knit sweater dress and leather jacket say casual while her chic wraparound shades and platform ankle boots have movie star written all over them.

Definitely keep this one in mind next time you’re scrambling for something to wear on your next flight.

Gwyneth puts a spin on a recent standby silhouette with a flowy white top that is crisply sharpened up by a very modern blazer and cropped pant. Symmetrical gold cuffs infuse some personality while still keeping the clean effect intact.

Gwyneth tames the flash of her Giuseppe Zanotti gladiator sandals with her daytime uniform of skinny J Brands and a well cut blazer. She paid tribute to her friend Stella McCartney by slipping a tee from her line underneath, creating the perfect casually chic look.

The perfect way to look drop dead gorgeous but still as elegant as can be — Gwyneth knows how it’s done in this Balmain micromini sequined dress and black blazer combination.

The blazer offers a little more cover so this looks sexy instead of tarty, and her wavy hair and square toe pumps are unexpected and cool.

A quintessential Gwyneth look — a creamy Stella McCartney ethereal dress is paired with a white blazer for a tone-on-tone effect, but patent oxford heels keep this from crossing over into saccharine.