Penny says: "I love these practical Helmut Lang pants and the warm, stylish sweater. The Sandro jacket with the zip off hem is versatile, it’s two jackets in one. The earrings jazz it up, and they are memorable."

Pants, Helmut Lang, $198; wool sweater, Iris & Ink, $220; wool-blend jacket, Sandro, $385; earrings, Ben-Amun, $98. All styles available at THE OUTNET.com

Sandro “Mael” Zip-Detailed Wool-Blend Coat $385 at THE OUTNET

Iris & Ink “Antonia” Ribbed Merino Wool Turtleneck Sweater $220 at THE OUTNET

Helmut Lang Cotton-Blend Wide-Leg Pants $198 at THE OUTNET

Tom Ford Metallic Python Ankle Boots $662 at THE OUTNET

Dolce & Gabbana Suede-Paneled Textured-Leather Shoulder Bag $948 at THE OUTNET

Ben-Amun Gold-Tone, Stone and Tassel Clip Earrings $98 at THE OUTNET