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Wednesday, September 10, 2025

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Winter Outfit Ideas

Did any of you know that it’s been a little cold lately? Heard it on facebook at all? The news? Nope? Haha.

Since the weather is all anyone can talk about these days, I thought today would be a great time to post some of my ideas for winter outfits. Dressing for cold temps and snow can be pretty challenging, especially if you have to look nice for work or an event. Here are a few of my ideas that I put together:

winter outfits collage

Casual:

Leggings, leggings, leggings! Comfortable, warm and easily slipped into tall boots, leggings are the perfect option if you need something casual. Ashley talked last week about her favorite ways to wear leggings, but here are a couple of mine.

Find a long sweater or shirt, and when it’s cold out be sure to layer up underneath with an extra tank top.

winter clothes 2

I also have a few big, long cardigans that are perfect for winter. Just pick a colorful or pattered tank to wear underneath and you’re set! This is a favorite of mine when I’m working in a chilly coffee shop since my cardigan doubles as a blanket.

winter clothes 5

 

Work

Work is a lot trickier when it comes to dressing in the winter, especially if you have a more conservative office. If you’re planning to wear tights or heels in the office, leave a pair of heels there and wear your boots while you’re commuting. If it’s super cold or you have a bit of a walk, you can even pull on some sweat pants over your tights until you get to the office. This might sound silly, but walk around Chicago this week – you’ll see women doing it everywhere!

winter clothes 1

Another option is to go with thicker tights or even fleece lined leggings underneath a dress or skirt. Also, if you’re tired of blazers and cardigans, try layering a button-up shirt or blouse underneath a sleeveless dress or top to add some warmth.

winter clothes 3

Finally, if you just can’t bring yourself to wear tights or if you have a little more wiggle room with your wardrobe, try some skinny legged pants with either ankle boots or riding boots.

winter clothes 4

 

Cold Weather Necessities:

COAT! When I first moved to Chicago I thought everyone looked ridiculous in their sleeping bag coats, as I called them. Come November I was singing a different tune. I went out and bought this North Face knee-length coat and never looked back.

north face coat

I absolutely love this coat because it really, really keeps me warm. I can easily get away with wearing a tank top underneath when it’s 30-40 degrees out and be perfectly fine!

Erin, from Loop Looks, also wrote a post yesterday about what coat to wear in Chicago (or similar weather).

Boots are also a very important one! I have a pair of Uggs, but it’s my Hunter rain boots that I rely on most during the winter months. They aren’t warm by themselves, but if you buy the liners and wear some thick socks, they’re great even in this –10 degree weather!

hunter boots

Why rain boots in the winter? Well we get lot of snow here in Chicago and their height keeps me from worrying about snow getting into my boots. Trust me, you’ll be thankful when the bus you’re getting off pulls up in front of a snow drift. Also – snow turns to slush when it gets too warm, which my Uggs are not made for.

 

How do you dress for the cold weather?

Do you own winter boots? What kind?

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38 COMMENTS

  1. Although I don’t work in an office and I have a lot more choive over what I wear to work, I’m all sbout staying warm over looking good. Once my feet get cold I’m cold for the rest of the day, so I love my winter boots. They keep me warm and dry.

  2. Love this! What brand of fleece lined leggings do you like? I’ve been trying to find some, but haven’t been satisfied with any options. Thanks!!

    • I have a pair of regular leggings that I love from Gap Body, but I haven’t found any fleece lined leggings. I’ve seen a few at TJ Maxx that I might try out!

  3. Great ideas! When I went to Purdue, my mom encouraged me to buy a big Columbia winter coat. It’s so warm, I still wear it today! I also traded in my pea coat for a warmer, down-filled puffy coat last year, and I’m so glad I did. Pea coats are cute, but not very warm.

  4. Haha. You’re a funny one 😉 I had NO idea that it was cold outside! 😛

    I really needed this post before Christmas. I would have added a couple of these things to my wish list! Leggings, waterproof boots, and a knee-length coat. If I see any good deals, I’ll still be getting them. I hate trudging through the snow to class everyday and getting my feet wet. And I’m always grumpy during this cold weather. The chill just gets to ya and it’s like the opposite effect of sunshine. When I feel the sun on my face in summer I just want to smile… When I feel the wind on my face in winter I just want to curl up into a ball and never venture out. Lol.

  5. Thanks for the shout-out! Love your outfit ideas. I need to get my ankle boot heel tips replaced. I miss wearing them.

    As for winter boots, I SWEAR by my Sorels. I made the mistake of wearing my rain boots to work the Chicago Marathon water station the year it was super cold and my toes nearly froze off. I’m in awe of those of you who can wear your Hunters all year round even with liners and socks!

    • I double layer if it’s really cold, but my favorite leggings I got from Gap Body. The long coat and tall boots help though because then just a bit of your leg is exposed

  6. AH I just moved to colorado from southern california and have been struggling to stay warm so I needed this post! I actually am borrowing one of the long insulated jackets right now from a friend and her hunter boots/liners. Both are heavenly!

  7. Katie, I’m so excited that you mentioned Hunter boots!! I have been wanting some for forever and my husband was kind enough to buy me a pair for Christmas, in purple!! I live in BC (Canada) and also think they’re the smartest choice for snowy/slushy days. A long puffy jacket is next on my list, I love that you call it a sleeping bag coat– I have a short one but keeping the booty warm is where it’s at.

    • My coat just goes down to about my knees, but there are some people here who have them that go down to their ankles – haha that’s where I got the idea of calling it a sleeping bag coat!

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