How a Texan Survived Chicago Winter Weather

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how to dress for winter weatherWhen I was packing for Chicago, I was honestly freaking out a bit. I’ve lived in Texas my whole life and a Chicago winter (even if it’s been mild this year) was nothing short of terrifying to me! Everyone I talked to said the key was layering – which is not something I excel at, if we’re being honest. Also I knew my short peacoat was not going to cut it and (even though I LOVE it), there was no way I was going to travel with my beloved vintage faux fur coat. So basically packing led to a meltdown. Okay maybe “meltdown” is a little melodramatic but STILL.

Dallas Fashion Blogger Valery Brennan81-web Dallas Fashion Blogger Valery Brennan14-web

Photos by Tek Chung

Here’s how this Texas girl survived – nay, dominated – four days in Chicago.

  1. Black and white. To keep things simple, I decided to pack all black and white. That’s what I wear most often these days anyway and I knew I could mix and match easily and add more layers in if necessary. Some button down shirts, a sweater, leggings, a t shirt dress and jeans were all I needed. Everything matched so I didn’t have to worry much about “outfits.”
  2. Smart shoes. As much as I desperately wanted to wear some cute loafers or even booties, I’m glad I listened to my gut. A snowy Chicago winter means you NEED boots and they have to be waterproof. A pair of faux patent combat boots and some duck boots served me well. Admittedly, I could have survived with one pair but I knew I would be taking outfit photos and wanted a bit of variety.
  3. Ridiculous scarves. I packed two scarves – a VERY long scarf that I could wrap around my neck and a faux fur infinity scarf. The faux fur scarf was a life saver because it also blocked the wind from my face.
  4. Layering. No matter what you think, one layer on your legs is NOT enough. With my coat and a long sleeved shirt, my torso was always warm but my legs were always FREEZING. Even leggings underneath jeans or two pairs of leggings wasn’t enough. You really need long socks and at least two layers of pants – three if you can swing it.
  5. Hoods. Have a hood available at all time. You will wear it often and it will seriously make all the difference in the world.
  6. Warm hands and feet. I got lucky and picked up a pair of leather gloves at Target on clearance right before we left and I’m SO glad I did. Without gloves I seriously would have been miserable and believe me when I tell you cotton gloves are NOT enough. Also regular socks probably aren’t going to do the trip. Try to bring at least one pair of long wool socks and layer your regular socks underneath.
  7. The right coat. Do NOT underestimate the power of a good coat. I’m bummed this particular coat is only available in a few sizes now but I cannot recommend it enough! It wasn’t super heavy or bulky but provided the warmth I needed – also it’s on sale for $39.99! Total steal.

Dallas Fashion Blogger Valery Brennan19-web Dallas Fashion Blogger Valery Brennan63-webDallas Fashion Blogger Valery Brennan21-webBy the way, you may or may not know the story of this “little black dress” – if you’re unfamiliar you have to go read this post before you go any further.

Now that we’re all caught up – you may think it’s insane that I’m wearing it again on this blog. I kind of do, honestly. But y’all this dress is SO comfy and so perfect for layering! I knew I was going to be wearing black jeans or leggings every day and I really wanted to try to work in a dress. With this dress, I was still able to wear two layers of leggings and still be relatively warm. The short sleeves meant I could highlight my white button down underneath. It’s always plenty warm inside buildings so I wanted to make sure I could take my coat off and still look pulled together.

Dallas Fashion Blogger Valery Brennan95-webDallas Fashion Blogger Valery Brennan16-web

Click on any of the bold links below to shop!

Coat: H&M ($39.99; exact) | Dress: Zaful ($10; exact; similar) | Button Down: Gifted (similar) | Bag: TJ Maxx ($29.99; similar; similar; similar) | Lips: NYX Matte Lipstick in Minx ($6.99; exact) | Leggings: Charlotte Russe ($10; exact) | Boots: Target ($20; similar) | Glasses: Polette ($17; exact) | Necklace: BaubleBar ($16 on super sale; exact still available!)


How do you survive the cold?! As much as I loved Chicago, the 65 degree weather here in Dallas wasn’t so bad either 🙂


4 thoughts on “How a Texan Survived Chicago Winter Weather

  1. I just went back and read through your post about that dress. I’ve never heard anything like it. That is HILARIOUS. But good for you for rocking it anyway! And thanks for the winter weather tips. I’ve been craving colder days but can’t complain about the beautiful weather we’ve been having in Texas lately!

    1. Hahahah it was seriously the most ridiculous thing but then I can’t stop wearing it! It was nice to get some real winter weather for a few days in Chicago but it was also nice to say goodbye to it!

  2. Honestly, I still tempt fate when getting dressed for cold weather. I’m a born and bred Wisconsinite and last week I walked out in leggings with a tunic (well, and a thick coat, etc) and it literally felt like I wasn’t wearing pants of ANY kind. But then I jumped into a warm car and forgot all about it. haha

    I stoked to see you style your LBD again in a completely different way. I haven’t tried the button-up-under-clothes myself but I’m dying to try it soon!

    Hannah | The Outfit Repeater

    1. Haha I do that a lot too buuuuuut here in Texas that’s not nearly as scary!

      This was my first go round putting a button down under a dress and I LOVED IT! I was afraid it would look and feel frumpy but it really didn’t!

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