It’s almost time to celebrate the new year! And if you live anywhere near me or in cold weather, welcome to the WORST of winter. For the next few months, I’ll be battling some pretty terrible winter weather if all goes as planned according to the forecasters. I won’t shoot the messenger, but I’m not excited about this one. Despite growing up and currently living in some of the coldest places in this country, I’m not a fan of cold weather. Maybe that means it’s high time I move somewhere warmer. But alas, life doesn’t really work like that most of the time. Plenty of good reasons keep us here in Chicago, so winter weather I shall endure.
But with all my experience duking it out with Old Man Winter, I have gathered up a handful of ways to transition just about any piece in my closet into something that can help keep me warm through the doldrums of gray and snowy winter months. So here goes sharing them with you! It’s all about layers, so let’s layer up this laundry list of winter style specials. We’ll start from the bottom and work our way up.
Forego the pumps and booties. When winter calls, embrace the flat (or nearly flat) boots. Tall boots really do provide so much more warmth than booties, and especially heels. And nix the heels. Ice and snow will undoubtedly get the best of you and you’ll be showing up in super cute, wet heeled boots with a really wet butt from falling in the snow. Probably wasn’t the look you were going for when you left the house this morning, right?
Sidenote: If you’re wearing winter boots for the commute, by all means opt for the pumps or booties when you’re inside. They are much easier to carry in your bag than a big ol’ pair of boots. Just know they won’t do you any justice once you step foot outside.
So warm and cozy! Let the functional layer peek out of the top of your boots for a bit of added interest and depth to your outfit. Your style persona will thank you.
Style Inspiration: Gray and teal option
I wear a lot of skirts and dresses to work. Not only do I think tights can be warmer than pants often times, but they slip perfectly into my winter or rain boots when bad weather comes to town. This season, fleece tights seem to be all the rage. I can’t argue with wearing fleece-lined anything to work, so I’ve definitely invested in several pairs and have made them a staple in my work attire.
If fleece tights aren’t in your repertoire, or just to mix things up, also consider trying to layer tights. Wearing two pairs of tights for added warmth and no one’s the wiser about your winter weather trick!
Style Inspiration: I’ve worn tights so often on the blog, it only makes sense to send you to a few posts I’ve discussed them including How to Wear Colored Tights at Work and Tights Are Back. Also, check out my Gallery and you’ll find a boatload of options!
At work, leggings are NOT pants. Let me repeat, Leggings Are Not Pants. But they make perfect tights. So wear them as tights to your little heart’s desire. They’re super warm and always make me feel extra comfy at work, almost like I’m cheating a bit. But no one’s the wiser!
Style Inspiration: After re-reading all about tights above, I wore leggings to work with my teal and gray dress.
Shirt Under a Dress
As long as the top layer, the dress in this case, is structured or thick enough, I can usually add a button down shirt or turtleneck under my dress.
Style Inspiration: This can be tricky to pull off without creating a bulky look. I’ll be sharing a future post with more details on tips to make this work. But for now, you can check out my chambray under a black and white striped dress. Scroll down to the comments where I offered some tricks to make this style work. I also wore a thin cream shirt under my floral dress, a green blouse under my cobalt dress in this remix, and a button down under my purple dress.
Shirt Over a Dress
Throw on a shirt over your dress as if the dress is a skirt. I’ve made some very summery dresses appropriate for winter with this trick.
Style Inspiration: Another potential tricky styling trick, I’ll share more details about this in an upcoming post. Generally, it works best with a belt. I utilized this option during the summer with a red shirt over my cobalt dress but also to transition a summery dress into cooler weather.
Nearly the same as the option above, though this typically requires a little less styling technique. The finished edge of the sweater takes care of the transition from top to bottom a bit better.
Style Inspiration: Here’s an option I executed recently.
Cardigan / Blazer
So many dresses have short sleeves or no sleeves. This doesn’t do me much good when it’s freezing out (or even just freezing in my office). Despite being a very common, run-of-the-mill option, I couldn’t complete this list of tips and ideas without including the obvious. So if you’ve got a favorite dress, don’t worry about the season for which it was intended. Add a cardigan or blazer, maybe a pair of tights, and you’ll make it perfect for winter.
Style Inspiration: As a pretty common option, I’ve thrown a cardigan or blazer over a dress many times, so you can browse the Gallery. But a few of my favorite options include this Suit Your Style series edition about How to Make a Jersey Dress Work for Work, my gray blazer over this black dress, and this navy cardigan with my teal and navy pieces.
Last but not least, I shared some inspiration from others and my tips on How to Dress Well in Not So Swell Weather. This should offer many other great ideas as well.