Silk Blouse American Eagle Outfitters Chiffon Poet Blouse ($44.95) WHY: It's a classic, feminine silhouette. There's something sexy about a silk blouse that's not too revealing, but at the same time looks effortlessly cool. Tuck it into a pencil skirt or wide-leg trousers for an "in-charge" work look, or wear it untucked with black jeans and booties. It's super versatile and always appropriate for every occasion.
Booties Boden ($188) WHY: They're easy to walk in! Plus, they look great with everything in your closet, especially in the fall. Trust.
Leather Handbag Stuart Weitzman Ceogrande ($770) Why: It's one of the first things people see when they meet you. We're loving these satchels because they have just enough room for everything you need and they look a little collegiate (yes, we miss back to school season!).
Jeans Dylan George Jane Mid Rise Fit & Flare ($198.00) WHY: They're the uniform of fall weekends — wear them with all of your cozy sweaters or with a leather jacket. Just steer clear of light washes, especially this season.
Wool Sheath Dress Boden City Tunic Dress ($198) WHY: This will be your savior on days you need to look pulled together—you barely have to think! Pair it with chunky statement jewelry or go minimalist with flats and a subtle pendant. When it gets cooler, pair it with tights and booties or tall boots with a heel.
Printed Scarf Spun by Subtle Lux ($52) WHY: It's the quickest way to take your neutral basics to the next level. If you've edited down your wardrobe like we've told you to in Wear This Now, you don't have a ton of "filler" clothes anymore. Everything should be relatively neutral and easy to pair with other things. A printed scarf makes a regular tee look finished, and can take a sheath you've been wearing to the next level.
Tall Boots American Eagle Riding Boots ($79.95)
Cashmere Cardigan Line knitwear ($229) WHY: It keeps you cozy and looking cool. As long as you care for it properly, it can last for years. Wear it with your tanks and blouses all season. Want more year-round fashion tips? Pick up our new book, Wear This Now, and find out everything from what to wear to an outdoor wedding to the best clean-out-your-closet-for-good tips! Head here to get $2 off your copy (and feel free to stuff it in all your friends stockings this season).