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Let’s face it: as cyclists, we’re obsessed with the weather. We check the weather the night before a morning ride, and again before we head out. Will it rain, be sunny, windy (a given if you’re in Chicago), snowing, humid? And whatever the conditions, deciding what to wear is critically important. Wear too little or too much and you could end up having a miserable time.

People often ask me what I wear while riding in different temperatures. In Chicago, we get both ends of the spectrum: frigid temperatures in the winter and extreme heat and humidity in the summer. For me, nothing gives me more pleasure than these first few cold Fall mornings. Without a doubt, it’s my favorite time to ride.

Many new cyclists tend to overdress when temps start to dip, whether commuting or riding a road bike. It’s better to feel a little cool when you first start out, as your body will heat up as your ride progresses. That’s a lesson most of us learn the hard way.

Fewer high-quality items in your cycling wardrobe makes more sense than a closet full of  jerseys and ill-fitting shorts that you never wear. Pieces that you can layer and combine in a variety of temperatures will serve you better.

I’m not advocating any one brand over the other. It’s about the functionality of these pieces. Personally, I prefer to spend a little more on a great set of bibs or a jacket that I know will last for years. I also prefer prefer an understated style, and the brands I wear create beautiful, classic performance wear for women.

The items I’ve presented below can be found in many brand lines, at a variety of price points. Whatever you choose to spend, look for great quality fabrics that are made well and backed by great customer service.

It's 40 degrees. What should I wear?