Lessons From Miserable Winter Weather

NEWSLETTER

12/11/20252 min read

It’s miserable in Chicago right now. It’s so cold, snowy, windy - my least favorite weather combination. However, the fashion has actually been quite inspiring to me. But probably not in the way that you think.

Of course Chicago is a big city with lots of vibrant looks. Right now though, people are bundled up like all they have left to wear in their closet is their ugliest outfit and they’re using every outerwear piece they have to try to cover it up. People are not dressed in their cute outfits. No, people are pulling out their biggest coats and wrapping a scarf around their necks so their heads pop out like a curious turtle.

Here’s what I’ve been loving most about these outfits: These extremely bundled looks are built from the most essential pieces that we wear day after day after day. It is the best modern example I can imagine of clothing pieces that are socially acceptable to wear on repeat with zero judgment. No one expects you to show up to the office wearing a different coat than you wore yesterday. No one is wrinkling their nose at you if you trudge through the snow wearing the same boots for the past 7 days. Most of us have a single big coat, one pair of snow boots, and maybe a couple pairs of warm gloves.

Historically, most clothing was like this. You had a small selection of clothing made to your measurements. You wore the same pieces over and over again. Clothing was mended if it got damaged. Pieces were made to be more flexible in sizing. You kept your clothing for many years and you wore each piece frequently.

Today, there’s an expectation that our style is going to be frequently fresh. There’s pressure to look different from yesterday, even pressure to look different than last week! If you wear the same shirt two days in a row you know there is going to be SOMEBODY that mentions it. Digging through my closet I’ve frequently had the thought “uhh, I can’t wear that. I wore it last week”. Personally, I find it exhausting and have started challenging this thought when I have it.

These days, I prefer to think of my wardrobe like pieces of furniture in my house. Beautiful pieces that I can feel good about investing in. Pieces that I am going to enjoy and feel comfortable in most days. Pieces that I want to take care of so they last for years to come. Pieces that I am okay wearing last week, this week, AND next week.

But when I explain this furniture idea it seems like it’s hard for people to connect to. This past week when I was people watching, and seeing all the different coats and boots as I drove down the snowy road, I felt the realization snap into place. That society's approach to winter wear is the approach I’m seeking in the rest of my wardrobe. It’s the idea I want to offer for consideration to other women and make available in the pieces I create. We can shop for the rest of our wardrobe just like winter wear. You’ve probably heard someone give the advice “invest in a good winter coat”. What if you started “investing in some nice fitting pants” or “investing in a go-to dress”.

Is it really that different?

person wearing jacket and backpack
person wearing jacket and backpack

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