Essential #1: Gray Sweater Dress—If you want to shop your closet, we recommend you sleuth out your favorite XL grandpa sweater. Otherwise all you need is this button-down oversized cardi to nail Mary's perfect knitwear option.
Theory Vented Cashmere Cardigan, $335, available at Theory, 8428 Melrose Avenue (at North Croft Avenue); 323-782-0163.
Essential #2: Updated Messenger Bag—It goes without saying that the PS 1 by Proenza Schouler is a modern classic. Why not opt for a navy version à la Mary, or spring for the just-debuted festive patent purse to solicit oohs and ahhs from all of your friends this winter?
Proenza Schouler Leather PS 1 Bag, $1595, available at Barneys New York, 9570 Wilshire Boulevard (at South Rodeo Drive); 310-276-4400.
Essential #3: Thigh-High Socks—Our counterparts on the East Coast may be trading in their thigh-highs for cashmere and wool tights, but Los Angeles is just mild enough for this perfect boot-and-socks mash-up. Pick a pair from local line Hansel from Basel for the ultimate in style and warmth—trust us, you won't regret you did.
Hansel From Basel Thigh High Socks, $32-$36, available online at Beklina.com, or at Creatures of Comfort, 7971 Melrose Avenue (at Edinburgh Avenue); 323-655-7855.
Essential #4: Knee-High Boots—The perfect knee boots are the ultimate investment—paired with socks, tights, or even a cute pair of fancy shorts, you'll be getting the most mileage out of this wear-with-everything style.
BDG Tall Pull On Boots, $68, available at Urban Outfitters, 7650 Melrose Avenue (at Stanley Avenue); 323-653-3231.