Two guidelines I live by are “It can’t be complicated” and “It has to be comfortable.” A biker jacket fits right in but lends structure to your casual look. Plus, it’s the perfect layering piece for chilly mornings when walking the dog or heading to brunch. SWEATER, $69, additionelle.com. JEANS, $142, nydj.com. EARRINGS, anntaylor.com. Roxy Earle x Le Château SHOES, lechateau.com.