I love hats, and with all of the inclement weather to come, they’re going to be more essential than ever! Fedoras are classically masculine, but women have been stealing the style for quite some time now (“anything you can do, I can do better,” right?). And while I’m not afraid to be one of the guys, I love having a woman’s touch integrated into my menswear pieces. In the case of this Rag & Bone wool topper (on ShopBop for $175), it’s the light pink leather strap. To make the look even more feminine, step into a bright, flirty skirt like this L’Wren Scott (at Barneys New York for $1,050). A slouchy bag (at Barneys New York for $895) from 3.1 Phillip Lim will contrast well with your pencil-thin skirt. And cover up in this Theyskens’ Theory cardi (at Barneys New York for $395) – the loose knit will keep you just warm enough in the autumn breeze.