One look from Pippa that left us seriously speechless was a plunging baby peach gown worn by the socialite when she stepped out at the Royal Parks Charity Gala, at the Serpentine Lido in Hyde Park in 2008.
As for the design, Pippa's dress featured pastel-coloured panels separated by striking black detailing and flatteringly cinched at her waist.
This time, Pippa wore her silky locks poker-straight and kept it consistent with her makeup look, once again opting for her winning combination of dark eyeliner, rosy blusher and nude lipstick.
Completing her outfit, Pippa added a white clutch bag. In photos from the dazzling evening, Pippa was seen chatting with close friends Olivier Inge and Charlie Gilkes, the brother-in-law of tennis icon Maria Sharapova.
Another fashion moment that left us inspired was a seriously stylish sister moment with Kate when the brunette duo enjoyed a summer outing at Ham Polo Club in 2006.
For the occasion, Pippa chose a chic strappy aquamarine sundress which she paired with cream wedges.
Meanwhile, Kate contrasted her lookalike family member, opting for a fiery red halterneck dress adorned with white polka dots.
Like Pippa, Kate chose a pair of red cork wedges adorned with a dramatic flower in the same letterbox hue.
The former Wimbledon champion on going professional at just 12-years-old and her advice for women attending tennis' most prestigious tournament this summer