Shop the Fall 2016 Trend: Heritage Hipster

Get the look: Authenticity is key, so narrow your focus to the reinvented classics, like outsize English tweeds, a cutaway trench, or flowy trousers that might seem extreme. Ask yourself, “What would Phoebe Philo wear?”

Ruell Floating Handle Hobo

Vince Camuto | $278

Ruth Ankle Boots

Sportmax | $645

Short Peplum Trench

Banana Republic | $178

Nine to Nine Shirt

Brooks Brothers | $58

Hens Single-Breasted Double-Faced Cashmere Coat

Calvin Klein Collection | $2,317

Gold-Tone & Leather Earrings

Marni | $390
Pionnière Bag
Prada | $1,940
Francesca Sweater With Choker Neck
Elie Tahari | $368
Sunglasses
Tod's | $405

Silk Shirt Dress

Tibi | $950

Charles Hound's-Tooth Single-Breasted Blazer

Preen by Thornton Bregazzi | $1,116

Circle Pendant Collar Necklace

White House Black Market | $50

Striped Wide-Leg Satin Trousers

Raey | $353

'Bonsai' Crossbody Bucket Bag

Simon Miller | $490