Shoe Trend Thigh High and Over The Knee Boots. The look of boots worn up until they reach your thigh is back, it's a very sexy and alluring look yet fashionable and chic at the same time. The thigh high boot trend was seen in countless designer shows such as Prada, Baby Phat, CHLOÉ, and MISS SIXTY. The look has also been seen on celebrities such as Rihanna, Lady Gaga and Christina Aguilera. Its a very daring trend but exactly how do you wear it... If you ask me pair this look with skinny jeans, leggings, skirts, tights, dresses and anything tight worn at the bottom to make your boots pop. It's a hot trend to try and the hottest look for this fall winter season. Look below to see how to wear this look.