Editor Street Style: Natalie Matthews

Courtesy of Joslyn Blair

Photo: Courtesy of Joslyn Blair

“This is one of my absolute favorite dresses. It’s basically the equivalent of a boyfriend’s too-big-for-you button-down, and it’s ridiculously easy and comfortable, but it’s also got a little drop waist detail and flared silhouette that make it feel more fashion-y. I love it, so I wear it all year round: When it’s warm out I pair it with bare legs and brogues, but today I added my warmest, thickest tights, beat up motorcycle boots, and a leather jacket with this perforated texture I just think is so, so cool.”

Dress: Thakoon Addition Gathered Front Shirtdress, $490; bergdorfgoodman.com

Leather Jacket: Iro perforated leather jacket, $1,365; blueandcream.com

Boots: Chloé; shop similar; Vince Camuto “Wellsley” boot, $139.99;

Tights: Wolford Individual 100 Tights, $78; bloomingdales.com

Sunglasses: Michael Kors Updated Aviator Sunglasses, $196; bergdorfgoodman.com

Bag: Everlane Magazine Tote, $325; everlane.com

Hat: unknown. Shop similar: Slouchy Beanie Hat, $14.82; asos.com