What I’ve Learned About Dressing for Winter (And 3 Mistakes to Avoid)

Winter Style by Liz-Urso.com

Does anyone else think that winter is the most difficult season to dress for? I thought I had things down to a science, but then I moved to Chicago back in 2016 and my winter style was thrown for an absolute loop. For starters, it doesn’t help that when it’s cold I tend to hit snooze twice as much as I do during the warmer months. So by the time I drag myself out of bed for the day, I’m already left with less time to get ready.

Now that I’m steadily into my second winter as a Chicagoan, I’m slowly getting into a groove of dressing functionally, but also in a way that makes me feel put together and stylish. But that didn’t come without some trials and tribulations (winter dressing is a marathon, not a sprint, no?). So today I’m sharing 3 Winter Mistakes to Avoid

But before I share those, let’s take a look at some of my favorite winter looks from the blog archives.

Winter Style by Liz-Urso.com

Winter Style by Liz-Urso.com

It’s really easy to stick to an all black wardrobe — especially in the winter — but I love adding in a bit of color to keep things fresh and interesting. Maybe that’s a colorful or patterned blouse or colored pant. But it could also be as simple as playful scarf or accessories that pop. Both these looks feature a bit of color — but the silhouette fits in with my standard uniform (tailored bottom and looser top).

Winter Style by Liz-Urso.com

And while it’s not rocket science — layers go a LONG way. Personally, I tend to run warm (i.e. sweat a lot) so I can’t wear too many layers. So for me that means I gravitate towards vests as my go to layering piece. This olive green trench style is one of my personal favorites and it’s a piece that works well now — but really is great in any season. A vest that’s multi-seasonal? That’s a win/win in my book.

Winter Style by Liz-Urso.com

Winter Style by Liz-Urso.com

If you’re looking for a way to add warmth and interest to your outfit, look no further than a good trench vest. A solid black style is a great basic that will get a ton of mileage in your wardrobe. I also love a slouchy woven vest that gives you that cozy pajama feeling — while also looking put together.

Winter Style by Liz-Urso.com

And it wouldn’t a winter style post without talking about cozy sweaters and cardigans, right? I thought I was a sweater addict and then I moved to Chicago and my collection doubled (maybe tripled! oops!). To keep things fresh, I look for pieces that add interest in one of a few ways — 1) color, 2) unique cut (like the asymmetrical hem above), 3) interesting length or design (I love a good tunic style).

Winter Style by Liz-Urso.com

Winter Style by Liz-Urso.com

So now let’s chat about a few things to avoid. Looking at some of these photos there are things that make me cringe now that I’m walking quite a bit to work for my commute.

Here are my 3 mistakes to avoid when dressing for the winter.

  1. Poor Shoe Choices — as much as I love my patent leather wedges of yester-year, there is no way I’d be caught dead commuting in those shoes (particularly on snow days like today). Stylish — and sturdy — boots are the best way to go. Sorels are my go to when the weather is throwing a major curveball. Some of my other favorite brands are Sam Edelman and Blondo. I wear my waterproof Blondo’s a lot and am highly considering adding another color to my collection.
  2. Don’t Get Caught Without Your Accessories — a scarf and pair of gloves are an absolute must have. I’ve frozen my hands one too many times walking with my ice coffee to the office so I’ve gotten into the habit of leaving my gloves in my coat pockets. And if you’re anything like me (see note about sweating above) find pieces that are easy to take on and off.
  3. Don’t Wait To The Last Minute — what I mean by that is try to plan your outfits. In the spring and summer I can get away with spur of the moment outfits much easier than I can in the winter. So avoid the headache of standing in front of your closet and tossing clothes left and right. Instead try putting together a few outfits on a Sunday evening or the night before work. I promise you’ll have better luck this way!

What mistakes have you learned from? Share yours in the comments.

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