I have a confession. I follow some amazing and stylish influencers on Instagram. And I see their posts with skirts and bare legs, or trousers with cute shoes and no socks…and I think, “I’m in Chicago!! There’s no way I could wear that!”.
I am envious on multiple levels. But alas, I do live in Chicago. And I’ve had to develop a winter style because it does get cold. So, let’s talk about staying warm in style.
Young and Ambitious
In my 20’s my style was more about fitting in and looking the part of the young, ambitious female executive. I wore plenty of skirts and dresses with pantyhose and heels. And would ride the “EL” (Our mostly above-ground mass transit system) to and from work and walk the few blocks on either end. Downtown Chicago is beautifully (in summer) and painfully (in winter) perched on the shores of Lake Michigan. And the aptly named windy city gets not just cold, but ARCTIC! And blasts of freezing air up your skirt is all I needed to declare “I’m moving to California!”.
Take the Good with the Bad
Yes, getting through a Chicago winter is a challenge. And, by stark contrast, summers in Chicago are so amazing! With Lake Michigan, 26 miles of stunning trails, beaches on the lake front, neighborhood festivals and concerts nearly every weekend. The summers are so amazing that I would forget that I wanted to move to California, until it was too late. Another winter was upon us!
I had no choice but to make peace with winter. That meant dressing accordingly. So, the curation of my winter style began. Let me share some of the key charasteristics/guidelines/learnings, honed over time, for staying warm in style.
Staying Warm — the Building Blocks
Base Layers
A thin, longsleeve t-shirt is my base layer most days. My go-to is white, but I also have black and grey. These are washed fairly frequently, so they tend to look dingey by the end of the season. Or, as I said in this post, white shirts are perishable. So, buy them in multiples. In winter I like them a little more form fitting, so I generally by them in size small.
Turtlenecks & Scarves
For me, there are areas that if they get cold, I’m cold all over. Two of these areas are my neck and my ankles/legs. I must keep them warm (or at least protected) at all costs. If not, I quickly slide into “I’m freezing” territory. For winter, I have a number of turtleneck sweaters. Or, if I’m wearing a crew or boatneck sweater, I’ll wear a bigger wool or cashmere scarf. This is very convienient because it can also be worn across your shoulders as a drape if you get very cold.
Hats vs. Hoods
I’m a big hat person in the summer, but somehow that’s never translated to winter. Probably because a hat still leaves your neck exposed. For this reason, my go-to winter coats have hoods. I do have a few coats without hoods, but they can not be worn on the coldest days
Outerwear
I have a lot of coats. There will be different occasions where a different coat will come in handy. Coats are seasonal items — and in Chicago’s stores, spring items will start showing up in February! We are still in the middle of WINTER. And all the coats are gone, sold out. So, my advice is that when you see a coat you like and might need, buy it! Over the years, this has resulted in me having a solid arsenal of coats for most occasions.
This Mackage down coat with fur collar/hood was an investment peice, and is at least 10 years old, but still looks great.
Natural Fibers
My love of cashmere is well-documented, as I’ve written about in this post. It feels amazing and is fairly lightweight but keeps you extremely warm. Cashmere sweaters are my 2nd layer most days. Wool is another material that will keep you warm. In both sweaters and trousers, wool is a natural fiber that will help regulate your body temperature.
Socks/Tights
I am anti-socks most of the year, but in the dead of winter my ankles and lower legs must be covered. And I’m not talking crew or trouser socks. I need coverage up to the knee. Here’s the tricky part, the weight has to be thicker than a trouser sock and not as bulky as knee socks. Call me high-maintainence, but I have found what works for me. These socks are just a little thicker than traditional trouser socks, but thin enough to not be bulky in shoes/boots and as an added bonus, have mild compression (which actually feels great!).
If it’s a super cold day and I’m wearing trousers or a long sweater dress, warm tights are a must. My love of barrel leg jeans and trousers is also well documented, but I have noticed that with all that extra room of the barrel sillouette, it can get a little breezy in winter. So, I often wear a thin pair of tights under my barrel jeans in the winter.
Footwear
In the winter, I wear ankle boots almost 100% of the time. I find them incredibly easy to dress up and down. I have casual and more dressy styles. And, importantly they keep my ankles covered and warm. I do have a few pair of full length boots, but hardly wear them anymore. The ankle boots look great with jeans, trousers and even most skirts and dresses.
Making Warm Fashion Choices
It took me a long time not to make fashion choices that reflected what others were doing, but left me cold and drafty. I had to really come into my own and have the confidence to stay warm in style…my style. I now know that if I’m warm and well-layered, I will feel better in my clothes. And that will be reflected in my general persona.
Winter in Chicago can be brutal and long. Once I figured out how to stay warm in style, winter became a little more tolerable. And after all this time, I guess I’m not moving to California.
WETSU! WETSU!
XO JT
