I don’t know about you but I really don’t think about my winter wardrobe until after the holidays. Truthfully, between Thanksgiving and New Year’s, my style focuses on stretching out the wear of my fall pieces as long as I can, and then quickly transitioning to holiday looks. Come January though, there is no getting around that winter is here! And the more winters that are spent in places like Chicago, the more it becomes necessary to really nail down the winter wardrobe pieces you need.
Now this post in not focusing on the cold weather gear you need for ski or winter destination vacations. But if you are looking for that, don’t worry! I have you covered here! This post instead is identifying those pieces that keep us warm but looking good and feeling stylish during these winter months!
I like to approach the need for winter essentials from the outward in. Meaning, focus on the items that you consistently wear on the outside. Having multiple options in quality coats and warm weather boots will make getting dressed in the winter more functional and enjoyable. Of course, the right accessories are a must. I love having a nice collections of hats, scarves and gloves to choose from. One simple accessory can easily update or change up a classic piece of outerwear. Finally, there are a few key clothing pieces that I want to touch on!
Winter Wardrobe Essentials
Grey Wool Coat // Saddle Brown Wool Coat // Plaid Wrap Coat // Nay Puffer here and here // Saddle Brown Puffer Coat // Chocolate Brown Puffer Coat
Saddle Brown Mittens // Grey Glittens // Pom Pom Hat // Grey Beanie // Navy Beanie // Oversized Scarf // Ribbed Merino Turtleneck // Thermal Long Sleeve Tee
Over the Knee Boots // Snow Boots // Waterproof Chelsea Boot // Lace Up Boot here and here // Slouch Socks // Short Wool Socks // Long Wool Socks // Oatmeal Sweater Dress // Grey Sweater Dress
If there is one thing I did right as my younger self, it was investing in quality coats while working in the corporate world! I am starting to bring out coats I have not worn in years! They are not just for dress up anymore! I love wearing a long wool overcoat with leather boots, denim and an oversized scarf as part of my everyday look! So take an inventory of any wool coats you have. I bet ones that have been sitting in your closet for years still work today. And even if they might feel “dated”, a simple trip to the tailor to rework shoulders, sleeves or changing up the buttons can breathe new life into them!
In addition, the good news about taking a look at your winter wardrobe needs in January, is the fact that you can find a lot of great items on sale. Especially when it comes to investment pieces like wool coats! There are so many markdowns right now that is is worth taking the time to look:
You simply cannot get through a winter in Chicago without a down puffer winter coat. My Patagonia down parka has served me well over the years. Perfect for walking the dog in, sitting in the stands at hockey games and throwing on over my workout gear. But it is the shorter puffer coats that are really on trend right now! I mean who wouldn’t want to snuggle into one!
To balance out the puffiness on top, wear a short puffer with your high waisted skinny jeans and lace up boots or with your favorite leggings and sneakers for running around town. I prefer the faux leather ones over the metallic ones. This one is a best seller. Slightly cropped and more fitted, it is gorgeous and the quality is great! The one I own here is a bit more oversized and longer (size down). I love it and get stopped all the time with people asking me where I got it!
For me there are two standouts here. One, an oversized scarf. I just cannot get enough of mine. I start wearing it in the fall with a leather jacket or blazer and take it all the way into winter pairing it with my wool winter coat. It never fails in keeping my upper body warm. The bigger, the better in my opinion!
The second winter accessory standout is a hat. I take my pom pom hats seriously. LOL! This one from J. Crew has served me well but I have a new favorite. The quality, construction and fit of this one is just so good. If a designer were to brand it, it would be four times as much! I personally do not look good in beanie hats but if I did, I would add this one and this one to my winter wardrobe. They look so good styled with a wool coat or short puffer!
Cashmere, wool and cotton. Natural fabrics close to the body not only help keep you warm but also allow your body to breathe. I want to highlight two pieces I currently love here. Both from Everlane of course! I love the texture on this merino wool turtleneck. With a close fit to the body, it keeps you warm but without the bulk. Also a thermal long sleeve tee is a layering piece necessity! Most of the ones I find are fitted which I do love but this boxier cut style is a nice choice too because it gives you the option for layering under or over other pieces!
No winter outfit is complete without boots! From snow boots to rain boots there are so many stylish but still functional options. Let’s start with snow boots! I love this Sorel boot for the messiest of winter days! They keep my feet and calves warm and dry while the heavy treaded bottom is great for slippery surfaces! But as much as I love them, they are a bit “heavy” for everyday. So I love these two options here and here for everyday winter ankle boots. Style them with with your skinny denim and exposed slouchy socks or tuck them into the hem of your straight leg denim.! To round out my boot collection for winter elements, I also like having a Chelsea boot on hand. Waterproof with a sturdy lug sole these are great for slipping on. Pair them with with wool socks for an added layer of warmth.
I am also adding a pair of boots here that might seem like an outlier but I truly cannot imagine winter without them. If you do not have a pair of over the knee boots you may want to seriously think about getting a pair. They are the perfect pair of boots to wear with skirts and dresses in winter. It takes the guessing work of how to keep your legs warm plus it negates the need to wear hosiery or fussing around with heels in the winter. This pair is on sale! But this iconic pair from Stuart Weitzman is on major sale right now too!
My sock drawer has been getting a makeover! LOL! And for winter, I am adding more merino wool socks. They are just the best to wear with winter boots. They are not too thick, keep your feet warm but not sweating and most importantly, they stay in place! Plus wool socks are a lot sleeker and chicer looking these days then they used to be! I am also really into wearing slouchy socks over the leg of my denim paired with short winter boots or rain boots. These ones here are so good!
Sweater dresses take the guessing work out of how to dress up in the winter. They are warm, comfortable, and look great paired with a tall or over the knee boot. Accessorize with a belt or leave it on its own. It is great to have at least one sweater dress in your closet!
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