What to Wear: Three Items to Winterize Your Summer Wardrobe

What to Wear: Three Items to Winterize Your Summer Wardrobe
I do not endorse walking around this naked in sub-zero temps.

Fall is here, and, in Chicago, we know this means that winter will also have its vengeance before long, and our city will unleash the snow and the winds that will make your insulated parka feel like a lacy shawl. For many people this is also the time when they put away their entire summer wardrobe and bust out their winter clothes. However, I have a confession to make. The confession is this: I never fully store my summer wardrobe. Because, really, I’m too poor to have two totally separate wardrobes and because some of my summer stuff is just too cute to pack away for an entire six (nine, in Chicago) months. In light of this, over the years I have had to get creative in order to make my summer stuff work for winter.

First, put away your puffy parka vest. I have seen too many women who think the solution to summer clothing in cold weather is the parka vest, and it is not. You just look like Marty McFly (not in a good way), and plus your arms are still cold. Pointless.

The first thing I recommend is going to be your staple in this project, the base for many comfy and warm outfits: a thick pair of insulated tights or leggings. It can be hard to find a pair that’s stylish, versatile, and don’t look like long underwear or running apparel. My favorite find have been these fleece-lined tights from Miss Woo’s, an online UK-base retailer. Awesomely comfortable and warm, I wear them all winter under any dress, skirt, or even the right shorts and stay (mostly) warm (because, hey, it is Chicago. Sometimes there’s no beating the cold). I also see a lot of girls attempting to wear their summer skirts and dresses on into cold months by adding only a pair of regular tights or leggings,  shivering their little tushes off, and then succumbing to jeans all winter. For the love of god, please don’t go out into the Chicago winter wearing non-thermal garments under your dress! I take no responsibility for the hypothermia that may or may not occur.

So you’ve got the bottom half of winterizing your summer dress/skirt covered, now on to the top. Just throwing a big coat over your sleeveless dress is not something I recommend for two reasons: first, you will get sweaty. Without anything between you and your coat, your bare underarms will sweat into it and cost you a fortune in dry cleaning. Second, your bare arms look out of balance with your thick leggings. And I know the first impulse is to grab that long-sleeve cardigan and throw it on top, which is perfectly fine, but personally I prefer a relaxed, long-sleeve blazer, especially with a summer dress. They also work really well over summery sleeveless tops.

Now, it is my personal belief that these two items alone are really all you need in order to comfortably winterize your summer wardrobe, however I can understand how an outfit still might feel incomplete without winter accessories. And now I get to talk about one of my favorite parts of my wardrobe and probably one of my favorite things in general, scarves! My best advice is: stop treating your scarves like things that purely keep your neck and the bottom half of your face warm, and start thinking of them as accessories and integral parts of your outfits. Invest in a collection of scarves in a material like pashmina that are thick and warm and serve their purpose, but also sit well and have movement so that you can keep them on inside after removing your coat, and let them add to your ensemble.

As you can see, it’s not hard to transition your summer items into cold weather, it’s really not. And don’t shy away from continuing to wear bright summer colors and patterns into fall and winter, as long as your accessories are more muted. I don’t subscribe to the thought that each season has to have its own color palette. I wear bright colors year-round and enjoy it. Be stylish, stay warm, and if I see you wearing that puffy parka vest, I will be so displeased.


How do you carry your summer items into winter? What other tips do you have? Leave them in the comments!


Leave a comment
  • Love this!
    Also, since crop tops were such a big thing this summer (and I was no stranger to the trend) I have been wearing mine over dresses and tights, and adding tank tops underneath. It adds an extra layer and means I didn't spend money on a tee I'll only wear for June/July/August.

Leave a comment