|$139, nine west|
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, $595, netaporter.com
2. Topshop patched army jacket, $110, topshop.com
3. French Connection cross-body bag, $68, frenchconnection.com
4. Nine West booties, $139, ninewest.com
5. J. Brand boyfriend jeans, $227, netaporter.com