15 Expensive-Looking Winter Outfits That Will Never Fail

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If there’s anything that feels more L.A. than a pair of blue jeans and ankle boots, it’s sunglasses in the winter. Being an L.A. native, I can confidently tell you that rain or shine, my sunglasses are permanently either attached to my person or within arm's reach. What can I say, you just never know when that sunshine is going to hit. Another thing L.A. girls have mastered that isn’t as obvious? Winter style that isn’t focused on puffer jackets and coats. From smart ways to layer to picking fun boots, we have this semi-cold weather dressing nailed down. To prove it, I asked five L.A. girls to show you their three winter outfits (sunglasses included) which resulted in some seriously cool looks I'm already re-creating. Keep reading to see what I mean.

Madison Chertow

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(Image credit: @madisonelainechertow)

Sunglasses of choice for winter?

I love the larger frames this coming season. I’ve been hooked on cat eyes, which is always a classic fave, but I'm ready to experiment with something that feels different than my usual.

What’s your L.A. story?

I’m actually an L.A. native (born and raised)! I’ve never really had a thought to leave the city either—it's always been my favorite place to be. From the weather, food, and the general lifestyle, I can definitely say it’s my happy place.

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(Image credit: @madisonelainechertow)

What are you adding to your winter wardrobe?

For winter, I’m incorporating chunky lace-up boots, oversize blazers and coats, and fun little mini bags (specifically from Jacquemus).

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(Image credit: @madisonelainechertow)

What’s one style tip you’ve received that has stuck with you?

I think the greatest thing I’ve learned is actually the most simple: Be yourself and don’t follow trends just to follow them. I always ask myself, Which ones speak to you? Which ones are classic, timeless to you as an individual? Always follow that, and always prioritize investing in the pieces that you’ll want to have for years on end that you truly identify with.

Amina Marie

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(Image credit: @aminamarie)

Where in L.A. is your go-to spot for some serious decompressing?

For serious decompressing, I love to go to Manhattan Beach to take in the beautiful water, beaches, and homes. The clean air and quiet atmosphere are so peaceful and also double as a great place for visualization—the neighborhoods are gorgeous!

What sunglass shape is speaking to you right now?

I love more fitted or slightly oversize sunglasses in the wintertime. I’ve been gravitating to a light cat-eye these days.

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(Image credit: @aminamarie)

Tell us about your winter wardrobe.

My winter wardrobe can be summed up as sweaters and boots! Even though it doesn’t usually get cold during the day in L.A., I love any opportunity to throw on a turtleneck and comfortable jeans and get cozy with a hot cup of coffee. I’m obsessed with a point-toe boot and think a nice pair of black boots can pull together just about any outfit. Raw-hem jeans? A #look.

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(Image credit: @aminamarie)

What do you think is the ultimate L.A.-girl uniform? 

I think there are two L.A.-girl uniforms: The ultimate L.A. girl-on-the-go uniform is still the oversize top or hoodie, chunky sneakers, and biker shorts. Very Instagram and admittedly incredibly comfortable (I was both ashamed and delighted the day I gave into this look). The second is casual chic, an oversize blazer, "effortless" hair, high-waisted denim jeans, and a unique shirt. This look pairs well with any shoe and feels like it fits in just about anywhere.

Elizabeth Villalobos

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(Image credit: @elizabethandreaa_)

What does your winter wardrobe consist of?

My winter wardrobe consists of blazers, satin tops, vegan leather jackets, pantsuits, puffy jackets, denim, animal print, color-block sweaters, bucket hats, pleather tops and bottoms, and tons of boots!

Black sunglasses: Y/N?

Yes. For winter, I love a good pair of round or rectangle black sunglasses.

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(Image credit: @elizabethandreaa_)

When did you know L.A. was the place for you?

I grew up in Los Angeles, and after moving multiple times away from here, I missed the people, culture, and fast-paced environment. I always knew this was my place to be; L.A. will always continue to inspire my creativity.

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(Image credit: @elizabethandreaa_)

Your tips on layering? 

I like layering pieces that contrast each other for an edgy, classic look. For example, I would wear a long coat and layer it with pleather blazer, chunky turtleneck, satin midi skirt, and a pair of boots.

Oby Grace

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(Image credit: @oby.grace)

What’s inspiring your sunglass style for winter?

I’m super into ’70s-inspired sunglasses right now. I love the shape and how it works with my personal style.

If you had to pick one winter piece from your wardrobe, what would it be?

I live in my teddy jackets during the winter; I have it in at least 10 different colors. It’s the coziest, comfiest winter piece, especially in L.A. when it’s very cold in the mornings and evenings. I love that it can be styled with anything and you will feel like you are walking around in a blanket. I highly recommend adding a teddy jacket to your winter wardrobe.

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(Image credit: @oby.grace)

What’s the one place you go to in L.A. that helps you decompress?

A good hike at Griffith Park always does the trick for me. It’s an L.A. must-do!

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(Image credit: @oby.grace)

What’s your L.A. story?

Since I was younger, I always wanted to move to L.A. I grew up visiting New York City every weekend and I loved it there, but I also knew that it wasn’t the place for me. So one day on impulse, I decided to buy a one-way ticket to L.A. with nothing but two suitcases, my laptop, and my camera. It’s been two years and I couldn’t be happier that I took that leap of faith.

Lizbeth Hernandez

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(Image credit: @imlvh)

What’s your eyewear of choice for winter?

Optical! I want to try taking a break from wearing contacts every day and wear my glasses out and about.

How would you describe the L.A.-girl uniform? 

To me, The L.A.-girl uniform is definitely a great pair of vintage jeans, a small shoulder bag, a cardigan, and a great pair of boots. L.A. girls are all about effortless and ease, and this outfit is polished and super easy to throw on but super comfortable too.

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(Image credit: @imlvh)

What’s your tip on always looking put together?

Experiment with fashion and find a good tailor, especially for your vintage denim. There is no such thing as buying the perfect pair unless you get it tailored to fit you.

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(Image credit: @imlvh)

What’s your L.A. story? When did you know this was your place to be? 

I was born and raised in L.A., so it's home to me and it will always be my place to be. I definitely feel lucky to call this place home.

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Nayiri Mampourian
Senior Fashion Editor, Branded Content

Nayiri is Who What Wear's senior fashion editor for branded content and based in her hometown, Los Angeles. It all began in 2014 when she landed an internship at the company and never looked back. While she does love writing her fair share of fashion stories, her heart really belongs in the brainstorm room, where she has fun strategizing different ways to create content with our fashion partners so that you engage with the brands you know and love. Her style tends to be more classic (she loves a good black-and-white look with gold accessories), and white pumps are kind of her thing. If she had to pick one person's wardrobe to raid, it would be Rosie Huntington-Whiteley's, and she also has a major obsession with interior design. She's a mom to a 1-year-old baby girl named Sophie, and she fully plans on training her to spot fashion trends by the time she's 10. That's all!