At the risk of sounding like a broken record, winter lasts approximately 83,384 months in the Midwest. Since I’ve lived here my entire life, I’ve practically become a pro at dressing for cold weather in a way that balances comfort and style. While there’s nothing wrong with it, you won’t catch me in full-on “winter gear.” Fun fact: I’ve lived in the Midwest for 30 years and don’t even own a pair of snow boots (I just wear an old pair of Chelsea boots). My ideal look this time of year is all about staying comfortable (comfort reigns supreme on dark, cold mornings, after all) without sacrificing my personal style. The way you look and feel impacts your mental health, after all! Here’s what that looks like in action.
1. maxi dress + socks + loafers + baseball cap + tote bag + hoops
A long-sleeve ribbed or knit maxi sweater dress is one of those wardrobe staples that, once you get it, you’ll wonder why you didn’t buy one sooner. They’re perfect for dressier occasions – work, church, dinner dates – but I also love wearing them when I don’t have any “special plans.” After spending too much time in lounge clothes, it’s important to switch things up, IMO.
This dress does just that without sacrificing style. For a fun take on a classic silhouette, pair it with more casual pieces like a baseball cap and a bucket tote bag. For a quirky finishing touch, add loafers with socks for a bit of personality.
2. leggings + long tee + sweater + hoops + socks + loafers
As you can see, I don’t have a personal vendetta against loungewear – I love my black leggings, too! For an outfit I wouldn’t mind being seen in outside the house, I like to dress them up with a long tee (one that covers the bum) and a layer on top, like a cashmere sweater. It’s oh so cozy and oh so chic. Small hoops add style without feeling too dressy, and the quirky socks-and-loafers combo has been one of my favorite ways to finish an outfit lately.
3. velvet pants + cardigan + loafers + bucket tote
I love these pants because, even though they look dressed up, they fit loosely around the waist, despite not having an elastic band. Styled up or down, velvet pants are a great compromise between style and comfort.
Burgundy is one of my favorite pops of color this season, so I’m making sure to get plenty of wear out of it before spring arrives. (Ah, spring…)
Looking for a break from brown and gray? Chocolate brown is a beautiful shade that pairs perfectly with burgundy.
Related: 9 Ways to Dress Warm for Winter Without Losing Your Sense of Style
4. black pants + denim shirt + sneakers + red sweater
Building your outfit around a pair of high-waisted, tailored (but nonrestrictive) pants is a great way to ensure you’ve got the style portion covered. A soft denim shirt and sneakers bring the comfort.
To complete the outfit and add a little panache, drape a red sweater over your shoulders. When it comes to pops of color in the wintertime, red is another favorite – and with Valentine’s Day approaching, I’m sure we’ll be seeing a lot more of it. Here’s your friendly reminder that you don’t have to pair it with pink!
5. striped turtlenck + black mini skirt + lined tights + knee-high boots
Yep, I’m still wearing mini skirts in winter – as long as I have fleece-lined tights, that is! (And as long as there isn’t an extreme cold warning… like right now.) In my striped turtleneck and mini skirt combo, I like to pretend I’m a French girl. This outfit is easy to recreate (just choose the skirt length you’re most comfortable with), stylish, and surprisingly warm. Somebody get this girl a croissant!
6. leggings + long tee + sweater + sneakers + socks + tote bag + wool coat
Another day, another leggings look. As a mom of two young kids, casual outfits are still very much a part of my lifestyle. From school drop-off and pick-up to a day at the mall letting a kid hog all the pretzel dogs from the food court (too specific?), black leggings always come in handy.
Of course, I like to elevate mine and add my own personal touch – as we all should! For me, that looks like the same long white base tee for extra coverage, a nice sweater, and an elegant coat. I still feel put-together with this casual outfit formula.
Comfortable and Stylish Outfit Ideas
Though I long for the day when we can throw on a spring dress and call it a day, there’s something to be said for embracing where you are and making the most of it. For me, that looks like outfits that still make me feel stylish – despite the temperatures. Oh, and hot coffee. Lots of hot coffee.
Looking for cozy outfits to wear? Up Next: 10 At-Home Outfits That Prove Comfy Can Still Be Chic
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