My Favorite Fall to Winter Transition Pieces

We’re in the awkward “in-between seasons” phase in the Midwest right now. It’s beautiful, seeing all the leaves change color and watching the frost melt every morning, don’t get me wrong, but it’s near impossible to dress for. However, after spending 18 years here, I’ve figured out my favorite pieces that can easily adjust to the random temperature fluctuations we see every ten minutes.

First, jackets! Any and all kinds. Jean jackets in multiple shades, multiple crop lengths, multiple sizes. I think I have at least four in my closet, and I just bought two more this season. The denim material is amazing at breaking wind, though it’s not great at keeping you warm, so be sure you layer it with a cozy sweater or sweatshirt underneath. Bomber jackets are also lovely if you need a little more insulation during cold mornings (thanks to those 8 a.m. classes for that) but usually warm up quickly once you get inside. I personally try to avoid down or puffer jackets at all costs, simply because I don’t think they add much to any outfit, and I can get the same level of warmth from a bomber. However, they are coming back in style, so if you love the extra plushiness they provide, go for it! 

Second, boots. To be completely honest, I wasn’t a fan of boots until last year; I always found them too heavy and annoying to put on. Last year, though, I figured out the magic of a good pair of boots and hiking socks. Nobody can see your socks, as long as your boots are tall enough, but they keep you SO much warmer. Knowing this trick has helped me get away with wearing skirts and dresses, with boots, all the way through our freezing winters without being completely numb by the end of the night. Booties are great for everyday or indoor wear; you still get the cute look without the added heat of a long boot. Pick a pair with a wedge or heel for a dinner out or for a presentation; you can still stay warm while looking cute!

doc marten boots for fall fashion Photo by Sergey Zhumaev on Pexels

Next up, I adore — like, ADORE — thermal layers. A simple thermal long sleeve will keep me as warm as a typical sweatshirt would, without adding any extra bulk. These are GREAT when I want to wear a pair of loose pants and still maintain some sense of my figure — without them, I’d be drowning in fabric! Thermal leggings also exist, though I still prefer insulated leggings (yes, they’re different).

Thermal leggings tend to be thinner; I’ll sometimes layer them under a pair of jeans if I know it’ll be super cold out, but only if I’m planning to stay outside all day. Otherwise, I don’t find the extra layer worth it. Insulated leggings, on the other hand, I wear on the daily. These leggings tend to be about four times as thick as your normal pair and have fleece on the interior, like a sweatshirt! I wear insulated leggings to practice and run errands all the time through the awkward transition phase and well into winter. 

I hope these clothing items help you make the weird transition from fall to winter a bit more effortlessly! Stay cozy!