For me, fall begins with a new boot (or two or three!). I need one in my arsenal that's right-this-minute looking and extremely versatile--i.e., goes equally well with a killer dress and an old pair of jeans . This black beauty pretty much nails it. Come the first hint of autumn chill, you might see me in...

1. Jason Wu striped sweater,
2. Topshop patched army jacket,
3. French Connection cross-body bag,
4. Nine West booties,
5. J. Brand boyfriend jeans,