Shop the look: 1. J. Crew bag, $98; jcrew.com 2. Uniqlo coat, $80 (originally $100); uniqlo.com for similar style. 3. Rag & Bone sweater, $325; net-a-porter.com 4. Moncler boots, $670; moncler.com 5. The Group by Babaton pants, $95; aritzia.com

When I think winter wear, I tend to think frumpy and lumpy. Too much unnecessary layering does more harm than good (awkward bunching versus keeping you warm). The goal is to be strategic. It starts with a sweater, as it always does (try a color-block one instead of a boring solid, and match it to your cross-body bag for a refreshed cold-weather look). After that, keep it simple with off-duty joggers, a no-fuss puffer, and winter boots that can tackle any winter weather mishap, because ain’t nobody got time for that.