I think I'm stating the obvious when I say transitional dressing can be tricky, particularly when you're going from summer to fall. You could start the day in a sweater to ward off the morning chill, only to be regretting your decision once the sun rolls around around noon. While layering is key, we also decided to round up pieces that will keep you looking and feeling your best no matter what the day's weather forecast entails. Think lightweight tops, timeless jeans and a boot or two to make everything a bit more fall-appropriate. Scroll to shop the pieces perfect for now and later.