Sweater: Jcrew | Gingham top: Jcrew Factory | Skirt: Urban Outfitters (similar) | Boots: Public Desire (similar) | Watch: Daniel Wellington (Use the code CLASSYKATEDW to get 15% off your purchase at | Bracelet: Kate Spade

I'm too obsessed with this outfit and I think the main reason is because it defines my style perfectly. The gingham under a sweater makes it classic and put-together but the untucked look, velvet and over-the knee-boots add casualness and a bit of edge. I'm still obsessing so hard over my over-the-knee boots because I can pair them with so many of my classic outfits to easily add a more chic and trendy twist. Also, they make it so much easier to transition skirts into colder weather because they cover up your legs!