Whether you're a fan of Kylie or not, you can't deny that Forbes' most recent cover model has some fearlessness when it comes to showing off her fashion sense! Personally, I wouldn't think to reach for activewear for a night out in Hollywood, but if anyone can pull it off and make us think otherwise, it's Kylie. She was spotted wearing these Alexander Wang leggings with a white bra top, and clear Yeezy heels to complete the most curve-hugging yet casual ensemble (maybe ever). Her top is from Naked Wardrobe, whose prices are actually quite wallet-friendly.

Playing the matching game with your pieces can be a bit tricky and border the line of dressing like grandma (especially with plaid), but Kristin Cavallari shows us how it's done in this mini dress and blazer by Alexander Wang. Simplicity is key here, with minimal accessories and black high heel sandals. We threw in a clutch idea to hold your lipstick and other essentials as you dash off for date night! Style your hair in sexy curls with a side part for a classic 1940s look that will finish this fun and flirty, yet polished look.