5. Madewell Silk Tulip Shorts $88
It's fun to see that shorts are not just for summertime anymore. They're now worn year round with bare legs during warmer months and with tights and booties/boots or even pumps during the winter. It's one of the easiest/most budget friendly ways to transition your summer wardrobe into Fall. And even though there are very "winter" versions (think wool, twill, and high waists), this also look amazing with the basic denim cutoffs. I usually pair mine with a thin sweater or slouchy tee and warm jacket, but blouses and flannels also look great. Are you wearing shorts this Fall/Winter?


