How to Style Winter Casual Outfits – cozy yet elevated

How to Style Winter Casual Outfits – cozy yet elevated

Does anyone else find themselves having a fashion identity crisis after the holidays? After months of wearing festive colors, plaid and even all the warm autumnal shades, what do I even wear? Who even am I?!

I want to be comfy, but in a “put together ready to achieve all her goals” kind of way. As someone who works from home, I am always one unplanned outfit away from throwing on mismatched Christmas pajamas and an oversized sweatshirt (iconic, really).

I am all about the casual comfy pieces that I can wear multiple ways! Neutral sweaters, sweatpants, everyday jeans, boots… sneakers! Today, I am sharing some of my favorite go to winter casual outfits!

Coats over Sweats – winter casual outfits

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outfit info: 1. taupe coat – 2. quarter zip sweatshirt – 3. sweatpants – 4. nike sneakers – 5. brown bag – 6. ralph lauren hat

I am one of the best versions of myself when I am wearing a light heather grey sweat set, a fresh blowout and my favorite perfume. It’s basically science.

I am a sweatpants connoisseur, and Abercrombie has the BEST sweatpants material and fit. They are like wearing your favorite sweatshirt, but as pants. Thick, soft interior, slightly oversized and they wash well.

Knee High Boots & Long Sweater Dresses

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outfit info: 1. sweater dress – 2. puffer vest – 3. brown bag – 4. knee high boots

Sweater dresses have been feeling a little outdated lately, until I found this oversized long sweater dress. Pair it with shape giving accessories (belt, coats, or this puffer vest) and it makes the perfect elevated casual outfit!

For the extra chilly days, I would style this dress with brown leggings (you wouldn’t even really see them) and these knee high boots.

Birkenstock Boston Clogs with Baggy Jeans

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outfit info: 1. navy pullover sweater – 2. baggy jeans (medium marble) – 3. birkenstock boston clogs (taupe) – 4. brown bag – 5. ralph lauren hat

I’ll take any excuse to wear my potato shoes (with socks only though… see how they still look brand new after 2.5 years?!)

Birkenstock boston clogs may be one of the most comfiest shoes I have ever worn, but they often make an outfit look a bit, well… less than chic. Sometimes I just don’t care (actually most of the time) however, the perfect pair of baggy jeans and a somewhat preppy pullover sweater makes a difference!

Wide Leg Sweatpants with Athletic Shoes

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outfit info: 1. quarter zip pullover – 2. wide leg sweatpants – 3. nike sneakers – 4. brown bag – 4. ralph lauren hat

This is the most basic outfit ever to grace my home office floor, but it’s important.

I work from home, but I am also a mom! I need to be casual, but I cannot function well when I feel sloppy. Neutral sweatpants that I can mix and match are a must!

Wide Leg Leopard Print Jeans – winter casual outfits

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outfit: 1. taupe houndstooth coat – 2. cable knit sweater – 3. leopard print jeans – 4. new balance sneakers (similar) – 5. brown bag – 6. ralph lauren hat

I thought I left leopard print back in 2017, but she’s back. She always comes back…

I am so intrigued by leopard print in general. Some years, it can look absolutely outdated and I want nothing to do with it. Then, a few years go by and suddenly it looks trendy again?!

If you are wanting in on the trend, these leopard print jeans are perfect! They have a stretchy waistband, so sizing is flexible.

Neutral Plaid Puffer Vest – winter casual outfits

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outfit info: 1. green sweater – 2. plaid puffer vest – 3. 90s jeans (dark) – 4. black boots – 5. brown bag – 6. ralph lauren hat

I am getting 2015 preppy vibes from this outfit, but I also think that’s what I subconsciously want. Life was just so simple back then!

Sometimes wearing a plain sweater with jeans can feel a little lifeless. I love adding accessories, casual hairstyles (a messy french braid would be perfect with this look) and a casual hat.

Sidenote: this ralph lauren hat was one of my favorite purchases this year! As simple as it is, it has really upped my elevated casual outfit game. It is chic, well fitted and goes with pretty much everything.

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