Making Your Wardrobe Work: Fall-To-Winter


Winter always has a way of showing up right when you’re really feeling good about the fall weather. Halloween was a great success, football season is heating up and you’ve finally nailed down some promising Thanksgiving plans. Maybe you’ve been rocking the hoodie-jacket combo for the last few weeks (a staple of my fall rotation), when all of a sudden one morning you’re on your way to the car and you’re hit with a blast of that frigid, winter wind. You check the date and swear to yourself winter comes sooner and leaves later every year.

There’s all sorts of challenges that come with winter’s arrival – treacherous drives to work, keeping your kids (or yourself) from going crazy with cabin fever – and looking halfway decent when you’re bundled up can be one of them. Winter style can easily turn into a layered hodge-podge of pieces from every other season. Most of the time we are just waiting for the cold to come to an end, and our style choices can often reflect our sentiments about this dreaded time of year. A few great winter pieces, however, can really fill the gaps from your fall wardrobe and make the season much more enjoyable for getting dressed and staying warm.

Because winter clothes are often only worn for one season out of the year, I tend to keep my essentials pretty neutral and basic. This way you can borrow from your fall (and spring/summer) wardrobe with ease. I will gravitate to the same coat or two every day when the weather is its coldest, so I really like having a navy or dark grey wool coat. It will look good with everything from khakis to beat up old jeans, and as long as it isn’t too formal it can look just as natural with a pair of sneakers from earlier in the year as it does with your favorite boots. A classic peacoat will always fit the bill, but if you are feeling more adventurous there are lots of interesting options that utilize the same fabrics and function with a more vintage or modern flair. I’ve found my personal favorite is a deck jacket, or a snap-front simplified version of a peacoat. My other winter outerwear is usually a parka. They can often be on the pricey side if you are buying a warm one, but it simply can’t be beat when the wind is blowing and the snow is coming down sideways. Personally I landed on a waterproof, middle-weight version that is easy to layer with my trucker jacket. A nice fitting denim jacket looks great worn over a t-shirt in the early fall, but it can also really add a cool dynamic to an otherwise simple winter routine. It will look great under topcoats, parkas, peacoats and pretty much anything else roomy enough to layer.

Vests are another great fall piece that you can transition from outerwear to in an inner layer as the bitter cold approaches. Style it just like you would the trucker jacket pictured above for an added level of warmth under a fall or spring jacket that might otherwise be too lightweight for winter. A lot of higher end coats will even come equipped with a button-in quilted vest. Living in the Midwest, it is nice to have the added layers too, as often times it’s cold in the mornings and warm enough later to leave the coat behind.

If by now you are a bit bored with all this talk of dark and neutral colors, I certainly understand. Winter is gloomy enough without having to turn your wardrobe into a pile of boring colors, right? Well fear not, because this is where we get to the fun part. By keeping your layers basic and timeless, you can have a bit of fun with hats and scarves during the winter. I love a red stocking cap, for example, to add a bit of style to an otherwise classic and functional winter wardrobe. Scarves and hats come in droves of colors and cool plaids, and you can find them at any price point. The best part is with a smaller add-on like these, you can take a risk on a new color without having to wear a bright green coat every day to work!

These are just a few ways to get you started transitioning that fall rotation into a winter wardrobe that will really work for you. As always, if you have any pointers or suggestions that have worked well for you, please feel free to share them below!