So much of the bicycling experience is the gear — including and especially what to wear at any given time.
I’ve become very picky about my clothing lineup for the full range of weather we get in the Chicago area. I have it down to 2-degree temperature increments, with humidity and wind factored in.
I didn’t seek out bike jerseys and shorts specifically by temperature, in most cases. I’ve gotten different jerseys for different reasons: to mark a place I’ve visited, to represent a team or school, because the design is nifty, or because it was a gift someone thought I’d like. My wife has made shopping for clever jerseys something of a sport, with great success.
That’s given me a range of apparel to work with. You wouldn’t think bike jerseys vary much, but oh, they do — in fit as well as thickness, even if subtle and even as they’re all made with sweat-wicking material.
And then there’s the all-important layering.
The basic layers
First, let’s summarize all that you’ll need for bicycling in the Chicago area all year.
Jerseys: Short-sleeve most of the year, but also long-sleeve. Thin and thinner, thick and thicker, up to “thermal” lined with fleece. I like having both tight (often called “sport” or even “race” fit) and looser (often called “raglan”) in my arsenal, but some prefer to have always looser or always tight jerseys. Then there are quarter-, half- and full-zips. The zipper is your ventilation control; I say the more, the better.
Shorts: The famous spandex — with padding, or a “chamois.” The chamois is a must. (And you should go commando, as explained here.) There’s an endless variety of shorts. They usually go midway down the thigh, but they can go a little longer or shorter. There are thinner and thicker varieties — and you usually pay more for durability, fit and comfort (for varying riding distances). There are also knickers, going down to mid-calf, and full pants covering your ankles; they’re typically thermal.
“Bibs”: Shorts that come with basically suspenders that strap over your shoulders. They usually have material to go down the center of your back, and they can have fabric covering your abdomen to varying degrees. But the point of the straps is a more stable fit, especially to keep the chamois in place so you have less friction.
Base layers: Skin-fitting, wicking T-shirts are the most common base layer, in short or long sleeves. Then there are thicker varieties, again thermal like long johns, for chillier weather. You can strategically wear, and remove, as many layers as you like over the course of a ride.
Arm and knee/leg warmers: Tight tubular apparel to cover your arms and the middle of your legs as needed in chillier weather, especially in early mornings. The big benefit is you can remove them easily later.
Jackets: For the chillier weather, there are superthin rain jackets and thin windbreakers. Then there are thicker jackets that may be lined to block wind or lined with fleece to keep warm, or both. There are also vests, blocking wind or lined with fleece. The tighter, the better for all of them.
Caps: A thin skull cap, under the helmet, keeps your head warm. A full beanie works in the chilliest weather. There are also helmet covers.
Socks: Yes, there are varieties of socks, too! Just like with running. Mid-calf or crew is the trend now in cycling. Ankle high or mid-crew is probably still most popular among recreational cyclists. There are no-show and knee-high socks, too. You can wear the length you prefer in given weather. But you’ll want a moisture-wicking material in any case. Maybe you’d like a thicker sock in colder weather, if it doesn’t make your shoes too tight. (Shoes are another topic.) The pros are wearing very slick, tight-fitting crew socks to supposedly be more aerodynamic; enjoy them if you wish, if you can get them on and off.
Dressing by temperature
OK, so here’s how I think about dressing after I look at the weather forecast each day. I’ll start with the perfect spring weather we had in late June and expand out.
70-72 degrees, low humidity: Short-sleeve base T. A good, solid, short-sleeve, tight jersey. Quality jerseys representing colleges come to mind; they’re often sturdy jerseys. Standard bibs.
68-70, low humidity: Does the low-humidity air bite a little? If so, I may need either the base layer or the jersey to have long sleeves. The breezier it is, the more I might need a little thicker jersey. I have an old team jersey given to me by a onetime A.G. Edwards employee that’s the perfect thicker jersey. I also think about the color: I may want a darker jersey to absorb the sun’s warmth.
66-68, low humidity: I’ll almost certainly need a thicker long-sleeve base layer or jersey, like the trusty A.G. Edwards jersey. Bibs provide a little extra warmth on the torso. I may need a skull cap.
66-72, humid: When the humidity rises and the wind calms, maybe I don’t need the base layer, especially once it’s around 70 and especially if I have a good, thicker jersey. Bibs probably are still best. I may or may not need a skull cap.
73-77, low humidity: A tight, short-sleeve jersey is perfect. I doubt a base layer is needed unless it’s particularly breezy. Could go bibs or shorts.
73-77, humid: Definitely don’t need a base layer. The jersey may have to get looser and certainly thinner. Still could go bibs or shorts.
78-83, low humidity: The jersey’s getting a little looser and lighter-colored if sunny. Bibs or shorts. This is perfect riding weather.
78-83, humid: Generally a loose, light-colored jersey. I may want shorts to skip the extra material on the torso.
84-89, low humidity: A loose jersey. Could go with bibs or shorts.
84-89, humid: Definitely a loose jersey that I will be unzipping. I often rely on my nice, light Greg LeMond jersey. Likely prefer shorts.
90-95: Now I want the loosest jersey possible with a strong zipper to yank down, and only shorts.
95 and above: If you dare ride in this heat, whether the jersey is loose or not and unzipped or not might not matter; it may be more comfortable to keep tight and zipped so the oven-like air stays off your body.
Go colder now
Now let’s go the other direction.
64-66: Long-sleeve jersey with base layer. Bibs. Maybe a slightly looser, thinner jersey if it’s humid. Skull cap in any case.
60-63: A thicker long-sleeve jersey, perhaps even at thermal thickness if it’s not humid. Or a thermal base layer. Bibs — unless the extra torso material is too much on top of the thicker jersey or base layer. Skull cap.
56-59: Definitely the thermal jersey or base layer, and bibs, skull cap.
53-55: Maybe both a thermal jersey and thermal base layer, and I may or may not want the bib’s extra torso material. A vest may come in handy to block wind on the torso while not overheating my arms. Skull cap.
50-52: At least a thermal jersey and thermal base layer, and maybe a tight T-shirt base layer, too. Bibs, skull cap. Maybe the vest again or even a windbreaker if it’s breezy or cloudy.
50-55, low humidity: Now I start thinking about a full windbreaker and even a beanie.
45-49: I’ve been wearing a windbreaking, fleece-lined jacket in colder weather on top of a fleece-lined, long-sleeve jersey but a short-sleeve standard base T; that’s the right amount of arm coverage for me. Beanie.
40-45: Now I’m wearing a long-sleeve base layer, too, often also at the fleece level. Beanie.
Under 40: Here’s where I stop riding, but I’m sure you know people who still ride with even down jackets. Here the challenge is keeping warm but also not sweating too much underneath, because that sweat can make you cold in the end, even dangerously so. Cold-weather bicycling really is a whole separate topic tackled by many writers.
Over a long day
Of course, the temperature or the weather overall probably doesn’t stay the same over a long day of riding. Or even a few hours.
So, layer accordingly.
It can be a challenge if I’m starting early in the morning when it’s in the 60s and it turns into a nice, sunny, 70something day later. I want to start with a base T and a jersey, maybe even long sleeves on one of those. Does that mean I’ll have to strip the base layer at some point? I’ve done it.
Or I have finally recently discovered the value of a vest for the early mornings. I can take it off and roll it up to store easily in a jersey pocket. I have started with thin rain jackets in the past, too, and rolled them up later.
Here’s where arm and knee warmers come in handy, too. I can wear arm warmers with the vest, then easily remove them later.
On chillier days, such as those starting in the 50s, the jacket definitely comes into play. I’ve also seen people wear fleece-lined jerseys over regular thin jerseys, then remove that top jersey when it gets warmer.
All in all, you have to adjust any and all of this to your tastes. Some riders seem to love even cold air on their bare arms, while others bundle up at the first chill. And it varies, too, by season; the 50s feel much warmer in March than they do in even May.
But right now as I write this in the middle of a heat wave, the best decision is riding outside the hottest times of the day, from late morning to late afternoon. Stick closer to dawn and dusk instead. And keep the clothing loose and yourself hydrated. Stay safe!
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