Mid-Winter Wardrobe Planning

We’ve got a long, long time until spring, yet already the fashion world is pressuring me to “refresh!” and suggesting that early January is the moment to break out a floral dress. There is mounting pressure to wear shoes without socks.


The next three months in Oregon will be cold. Rainy weeks might be broken with a few glorious days of sun, or we could get an inversion of fog that leaves us unable to see the sky for days. Family schedules will resume at a hectic pace. Work will spiral around me with deadlines and expectations. But I plan to enjoy each of these busy, bad weather days and look good while doing so.

Here is my winter wardrobe planning checklist. I’ll knock these out in early January to make getting dressed easy all winter long.

Hello, beautiful winter.

Be realistic about your winter

“There is no bad weather, only inappropriate clothing,” my husband tells the students in his outdoor, environmental literature class. They are expected to go outside for class, everyday, no matter the weather. We should do the same ourselves. Warm, durable clothing that can withstand a little mud is a must. A stylish, well-fitting winter coat and good boots can make the worst winter storm a fun day for a hike.

No day is a bad day for a hike.

That said, don’t live in a fantasy winter. Recently I found a great pair of NorthFace ski pants at a quarter of the original price. As I headed up to the register a little voice in my head said, “But… you don’t ski.” I argued with the voice that I wanted to learn to ski and that maybe if I had these great pants I would. The little voice reminded me that I hadn’t bothered to learn to ski for the last 44 winters. I reminded the voice that these were great pants. The little voice in my head gave me a look (or whatever) I put the pants back.

There are a lot of fun winter clothes out there, but I only need the ones I will actually wear. In Oregon, a silk base layer, warm wool and flannel, and a well-crafted rain jacket suit me perfectly. Check to make sure you have the gear you need so you can get outside as much as possible, but don’t pretend you’re mounting an expedition to Denali, even if you find a gorgeous ice axe for half price.


Pack up the fall, pack in the winter

By January I am over the rich browns and warm oranges of my fall wardrobe. My winter tastes run to gray, navy, jewel tones and a few pastels in warm wool or cashmere. I like to take time to pack up a few fall pieces, and pull out the deep storage of gray wool sweaters.

Make sure everything hanging in your closet is something you want to wear now, and pack up the extras for a much deserved winter rest.

Welcome back, gray wool sweater with rainbow hearts!

This is also a good time to think about how your fall wardrobe worked as a whole. In your style notebook, make a few notes about what you loved and what didn’t quite work. Looking back, I had more choices than I needed this fall, and that slowed me down every morning as I got dressed. Next fall I’d like to tighten up my choices. Take a good, hard look. Are there any fall pieces that just didn’t get worn? Now if the perfect time to send them off to the resale shop, or hand them down to a friend who can get some use out of them.

It just wasn’t meant to be.

Check for comfort, watch for sloppy

It’s a steep decline into wintertime sloppy, isn’t it? The weather is miserable, you woke up late because it is still so dark out, and really, it would be fine if you wore that old sweatshirt just this once, right?

Three weeks later you are trapped in a rotation of two sweatshirts and a pair of jeans that haven’t looked good since 2012, and have no idea how to escape before spring.

I bought this on the way back to Oregon after Shayla and Eric’s wedding. I believe their oldest son is now in college.

Check your winter wardrobe to find plenty of comfy ensembles that look as good as they feel. You deserve to be warm and dry. By having an advance plan for those dark, dreary mornings, you will be less inclined to reach for the old sweatshirt.

Cozy and stylish

Take a break from buying

January is a great time to give your hunting and gathering skills a rest. I feel like I spend all fall finding gifts, tweaking my wardrobe, cozying up my house. By January I’m ready to leave the world of commerce for a while. Sometimes we get so into the habit of shopping that we forget how much we have. While there are crazy January sales happening all around me, I’m just going to opt out for a month or two.

Looking inside, rather than outside of my closet for the perfect outfit forces me to think more creatively, and helps me to appreciate the good choices I made in the past.

I could go shopping, or I could stay home and play with my goat!

The still, gray winter skies of Oregon inspire me to snuggle in, reflect and be grateful for the comforts of home. Winter has its challenges, to be sure. But a comfortable, weather-proof wardrobe frees me up to play in the rain, and the decision to keep it simple allows me the time to do so.


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