Fedoras have had a bad reputation for some years now, being most commonly associated with irony, hipsters, and all of the other Brooklyn clichés. But while beanies will do for the chilliest of days, their casual, slouchy shape doesn't work for all occasions. Take a cue from Jessica Alba and give that fedora a second chance. A slightly oversized brim and a deep hue like navy or black is forgiving on bad hair days and adds polish to the simplest of outfits, like her cardigan and jeans combo. As the temperatures get colder, it's also handy for keeping your head warm. Just watch out for an errant gust of wind.
Bailey for J.Crew felt hat, $98 at J.Crew