What to Wear in the Winter in Los Angeles

Welcome to Before I Head Out, a monthly series in which fashion editor Anneliese Henderson rounds up the snaps she’s taken of her favorite outfits before heading out the door of her Los Angeles home.

Oh, the weather outside is… well, nice. Like, extremely nice—I can’t lie. I live in L.A., where the temps dropping below 60 degrees in the daytime is a rarity that I personally get kind of excited about. We might not have a real cold season like other parts of the world, but it doesn’t stop us fashionable Angelenos from embracing winter fashion. We just do it a little differently. I, for one, turn to things like barn jackets, suede boots, and opaque tights. I even, *gasp*, have an ankle-length peacoat that makes an appearance when the wind picks up in the evenings. (You don’t know cold until you’re walking by the beach past sunset in January—trust me.) So if you’re like me and looking for cute pieces to survive this so-called winter we have here, or for something to wear on your escape from your real winter, I’ve got some outfits for you. Keep scrolling to see nine chic looks that I’m wearing on repeat these days.

(Image credit: @annadzhenderson)

If you walk into the Who What Wear office on any given day, the chances of seeing a barn jacket are incredibly high. I snagged the perfect lightweight one for L.A., but there are options with a little bit more fabric if you need something for a colder climate. Here, I paired it over a ribbed long-sleeve (that may or may not be my pajama top… I’m just trying to stay cozy 24/7), my new Freja NYC bag that’s been earning me compliments every time I leave the house, and my trusty Dior loafers.

(Image credit: @annadzhenderson)

Yes, I’m in a long-coat outfit, because sometimes, I just want to cosplay as a winter girl. This really is my uniform. Cute top, Free People barrel jeans (I have them in every color), kitten heels, and a coat. This look always makes me feel polished and cool. Pro-tip for your barrel jeans: If you’re 5’9″ like me, order them in the tall length.

(Image credit: @annadzhenderson)

I’ve been an advocate for denim on denim for a few seasons now, but this dark-wash pairing is my latest go-to. I usually just wear the denim jacket as a shirt (it’s L.A., so layers are optional), but occasionally have a little white tee poke out from underneath. When it comes to finding the perfect set, the denim washes don’t have to be the exact same, but they should be in the same color family. No need to worry about buying pieces from the same brand. This top is from Mango and the bottoms are from PAIGE—two completely separate purchases at different times of my life, but they happened to go together seamlessly.

It’s been a month since we got my puppy, Rosewood, and my time spent in the house has increased tremendously. I love staying cozy, and this Daily Drills set is my new favorite thing. I can wear it around the house, but it’s also perfect for walks around the neighborhood with my girl.

(Image credit: @annadzhenderson)

If you see me on the regular, you’ve probably seen this Almina Concept sweater. You might not think I wash it, but I swear I do—I just wear it a lot. My fellow editor Anna LaPlaca couldn’t stop raving about it last year, and I finally got my hands on it a few weeks ago. I pair it with all sorts of things (maxi skirts, trousers, miniskirts), but jeans and flats are my go-tos. It elevates my look so easily.

(Image credit: @annadzhenderson)

December was filled with holiday functions, and this Old Navy minidress helped me look chic while keeping my finances in order. The dress looks and feels expensive, but is somehow only $25. (Yes, $25!) I’ll be wearing it well past December but if you want something a bit more timeless, it also comes in black. I finished off the look with opaque tights (because hey, it gets cold at night!) and pointy kitten heels. Easy and chic.

(Image credit: @annadzhenderson)

My manager, WWW’s fashion director Michaela Bushkin, and I have a habit of matching on the regular. So when we discovered that we both bought this blazer, we were not surprised in the slightest. It has a matching brown skirt, but I opted for my trusty black mini. Both options work beautifully.

(Image credit: @annadzhenderson)

I think my exact text to my friend when I put on this cashmere was, “OH MY GOD IT’S PERFECT.” Or something along those lines. This sweater is divine—the fit is heavenly, the fabric is oh-so-soft (I mean, it is cashmere), and the color is right on trend. My suede Reformation bag and dark-wash Khy jeans were the perfect additions, if I do say so myself.

(Image credit: @annadzhenderson)

These pops of red made me feel festive for the holidays, but I’ll definitely wear this look for the rest of the year. I left my coat untied, as it’s more of an accessory than a necessity (remember, we’re talking L.A. winter here).