I’ve been a Dressember participant since 2014. This means some of my experience with Dressember was in the warm and mild winter weather of Central California. A few years ago, I made a huge effort to wear a dress every day even when I was working from home or didn’t particularly want to get dressed. Since moving back to Colorado, Dressember has been a fun challenge each December & I love that even though I almost do it all by myself there are several friends who love to cheer me on!
Leggings & Tights – I couldn’t do Dressember without leggings and tights. After 2018, a friend recommended wool tights, she swears they are warmer than anything else she owns and she enjoys wearing dresses in December and the winter months. I snagged a pair in the summer and I’m eager to see how warm they keep me. Otherwise, I wear Pact Apparel Leggings in Navy & Gray, and I have a few pairs of fleece-lined tights from Target that are impressively warm.
Dress slip – get one. This is a life changer to how I do Dressember, especially when wearing tights and leggings. It’s another layer between me and the cold plus it keeps my dress from riding up. Mine also features a wire free bodice so I don’t have to wear a bra with it!
Socks – Knee high socks are a fun alternative to leggings on mild days. Ruffle ankle socks are a great alternative way to dress up ankle boots sans leggings and tall socks are a good alternative to tights and leggings on warmer December days. I tend to add warm wool socks to my not wool tights or leggings to keep my feet warm.
Boots, lots of them – while living in CA, I was able to wear flats and even sandals during December. Now it’s most definitely boot season. I have tall snow boots, cowboy boots, rain boots, lace-up boots, & Chelsea boots. I also plan to wear my clogs with socks.
Layers – oh all the layers…getting to actually share what my entire dress looks like during Dressember in Colorado is a rarity. I layer with sweaters, cardigan, jackets, and vests. Not to mention scarves and snow parkas on really cold days.
Whether you live somewhere where it’s mild in December or cold, you can do Dressember but you’ll want a strong supporting cast of layers and fibers to carry you through the month! Don’t forget you can wear jeans under dresses but they aren’t much warmer than leggings or tights in my opinion.
Will you join me this December in wearing dresses or ties every day to show that femininity is not a weakness? To stand up for the millions of people that are held in bondage today? Let’s be abolitionists, together.
Stylishly Shelby 
Nice vintage sweater on day 5 last year 🙂