Summer's spoiled us with a pretty minimalist dress code — you need (and want) little else on your body but a sundress and sandals — but Fall's cooler days ahead are about to change our one-step style. To ease through tougher transitional times (we're talking weather here), we've cultivated a bit of a styling workshop: five awesome pieces that are just as easy to dress now as they are later. Think silky button-downs and a staple maxi skirt. And if you don't already have them in your closet, then we highly recommend investing now. Need the proof? Step inside for five season-defying finds and 10 awesome ways to wear them.
How to Take Your Ankle Boots Through the Seasonal Shift
Trying to figure out how to transition your warm-weather pieces for Fall is a weighty issue — and replacing your sandals in favor of socks and boots can often be a near-tragedy. Luckily, there are a number of ways to start incorporating your beloved ankle boots into late-Summer looks and making them pull double-duty for the seasonal shift. We've helped you out by taking three pairs of chic ankle boots and showing how seasonless they can be. Click through to see and shop six looks that work stylishly for late Summer to Fall.
Key Transitional Piece: The Lightweight Sweater

Even though we're still in the thick of Summer, it'll only be a matter of time until we're facing crisp, cool temperatures, falling leaves, and brisk evenings. A key piece for this transitional time is a chic, lightweight sweater. As executed by Ashley Olsen, Emma Stone, and Katie Holmes, it's a staple that is not only perfect for braving any evening chill, but is also easy enough to stash away in your bag if you start getting hot. Whether it's a slouchy, easy-to-layer basic or an oversized poncho silhouette à la Ashley, click below to shop the perfect transitional sweater for high Summer.

