CASUAL WINTER OUTFIT IDEAS

Admittedly, I’m not a super casual dresser. It’s not a coincidence that I choose to live in a place where if I want to walk down the street in heels and a fancy dress at any hour of the day or night, no one will blink an eye. But that being said – I definitely dress comfortably and practically on the weekends. And since we’re about to head into a nice long, relaxing weekend I wanted to share a few casual winter outfits I’m loving right now. The full try-on session is over on IGTV, but details are here for each outfit.

The fun thing about winter is that you can definitely play with extra prints and textures. Don’t be afraid to layer in a striped turtleneck. Or a metallic vest. Instead of jeans, try a pair of corduroy overalls or velvet jeggings instead. Casual doesn’t need to mean boring. Race you to the long weekend?

P.S. There are a few pieces you’ll see here that are older from my closet. Wherever possible I linked the exact items and in a few cases I linked the closest alternative I could find.

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CASUAL WINTER LAYERS

The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket

Last week, as we entered a new year – I took a quick poll on my Instagram Stories to hear what you wanted to see more of on the blog in 2018. And one of the things you all resoundingly agreed on was budget-friendly looks and casual style. I get it – a frilly dress is fun and all, but when it’s freezing cold and you’ve got to go run errands, all you really want to see are ideas of how to look reasonably cute while staying warm. So for my first new outfit post of the year I’m sticking to price-concious, casual winter layers. And I plan on bringing you lots more where this came from in the new year.

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This outfit is exactly the type of thing that to me – makes winter dressing a little bit more fun. I’ve got lots of layers on (including tights under my overalls to be sure my legs didn’t get too cold), but the mix of textures and pattern saves it from feeling boring. I originally got this floral puffer jacket back in the Fall (see how I first wore it here), but with the addition of a thin striped turtleneck, thick sweater and these overalls – it stands up pretty well to much colder temps. It’s good to find ways to shop your own closet across seasons. Plus, I’m already sick of my black puffer jacket this winter and we’re only 1 week into January.

Lands’ End Floral Puffer Jacket c/o | Striped Turtleneck | Knit Pullover Sweater | Sole Society Suede Booties c/o | Anthropologie Knit Pom Hat | H&M Overalls | Burberry Lipstick in Bright Plum c/o

The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket The Steele Maiden: Casual Winter Layers - Floral Puffer Jacket

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4 CASUAL HOLIDAY OUTFIT IDEAS

The Steele Maiden: Casual Holiday Outfit Ideas - denim, sweaters, blazers and vests

If it’s any indication what November was like at work for me – know that I shot all of these looks over the past month and am only now getting the chance to find time to post them (I’m ready for you Christmas break!). In any case, now that I’m ready I figured I’d compile them since they all have a bit of a common theme – festive yet comfortable. Below, a closer look at these casual holiday outfit ideas:

The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans

I picked up this oversized red sweater during Black Friday sales and honestly can’t stop wearing it. I’ve dressed it up with heels and a skirt for work, but I like it with boyfriend jeans, fancy flats and a fisherman’s cap too for holiday shopping or weekend errands this month.

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The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans The Steele Maiden: Casual Holiday Outfit Ideas - red sweater and boyfriend jeans The Steele Maiden: Casual Holiday Outfit Ideas - overalls and metallic sweater

It’s been awhile since I last pulled out my overalls but I quickly remembered why they’re my favorites (spoiler: SO comfy). Dressed them up a bit with this metallic striped sweater and metallic kitten heels and this outfit made going to the grocery store for cookie baking supplies all the more merry.

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The Steele Maiden: Casual Holiday Outfit Ideas - overalls and metallic sweater The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers

I’m calling this my tree-trimming outfit. I love a good puffer vest in the winter – and all the better if it’s in tartan plaid – and I’ve been wearing these sneakers non-stop lately. I spend a lot of time in heels, but sometimes you just can’t beat a pair of comfy kicks. The olive green feels a little Christmas-y too which I love.

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The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers The Steele Maiden: Casual Holiday Outfit Ideas - plaid puffer vest and sneakers The Steele Maiden: Casual Holiday Outfit Ideas - velvet blazer and plaid heels

This one is a little bit unexpected, but no less festive in my opinion. I like mixing in colors like bright gold or deep navy blue to holiday style and this velvet blazer and plaid heels are just the ticket. Mixed with fun socks just because.. more is more this time of year, right?

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The Steele Maiden: Casual Holiday Outfit Ideas - velvet blazer and plaid heels

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CASUAL SPRING STYLE: OVERALLS AND LEOPARD SLIDES

The Steele Maiden: Casual Spring Style - Denim Overalls and Leopard Slides

I’ve been sharing more of my everyday outfits in real time over on Instagram Stories (do you watch these? I think they’re such a fun way to instantly connect with you all) and last week I took a quick snap of this exact outfit and was blown away by how many of you sent me direct messages saying you loved it! So I figured I’d take a few more photos and share them here.

ps. As always – I love to hear what you guys are loving or want to see more of! Reach out via email (jessicaATthesteelemaiden.com) in the comment section here or on Instagram.

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WEEKEND STYLE: OVERALLS AND STRIPES

The Steele Maiden: Weekend Style - overalls and stripes

I’ve been eyeing overalls for more seasons than I’d like to admit at this point. On cool girls in coffee shops, on Pinterest, everyone was pulling them off with ease. But for some reason I felt like on me they’d be all wrong. But then I reminded myself that I tried wide leg chinos recently to happy results and so I finally decided to give it a go. This pair was less than $40 and as evidenced here – we’re getting along just fine.

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