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Behold the cycling cap, the sport’s most disputed accessory, in forms both useful and useless.

Maybe you wear one faithfully, or you institutionally hate them, or you don’t understand why people even make them anymore. We’re talking about cycling caps, perhaps the most polarizing accessory in our sport. Adored by our forebears and cast away by the contemporary peloton, they serve utilitarian purposes that make them worth considering.

Cycling caps became popular in the 1950s and were worn well into the early 1990s, when helmets became more common in professional riding. It wasn’t until the early 2000s when helmets became required that the cycling cap started to become a relic of the past.

After 2003—when the UCI enacted the “all riders must wear helmets” rule for professional cyclists following the death of Andrei Kivilev during Paris-Nice—the cycling cap lost its definitive role atop riders’ heads.

But cycling caps didn’t go away altogether, their use just became more specialized. Practical reasons for wearing a cap include keeping sweat off your brow, preventing rain from dripping down onto your face (thanks to the cotton liner), shielding your face from the sun (in the case that the sun is perfectly poised above you at high noon and the short brim can actually be of service), and to keep your head just a touch warmer during the spring and autumn seasons, when a light layer can protect you from the chill.

Cycling caps should fit snugly under your helmet without adding pressure points. A well-fitted cycling cap should provide added protection from wind, rain, sun, and glare.

Cycling caps come in thermal, moisture-wicking, and old-fashioned, non-technical cotton varieties. Each material has its own strengths for specific types of riding.

Wool is ideal for cold-weather cycling caps, keeping you warm after it gets wet. Some fabrics, like Pearl Izumi’s Transfer, combine merino wool with synthetic fibers like polyester to form a lightweight and durable blend.

Apparel manufacturers use a number of proprietary and licensed synthetic fabrics, but they tend to amount to some combination of polyester, nylon, and spandex. Synthetics are versatile because they’re lightweight and breathable, and can be woven, used in mesh, or employed as yarn in fleecy microfiber fabrics. Some have UV-resistant fabrics to shield you from the sun or are coated in Durable Water Repellent (DWR) that sheds rain.

If you opt for cotton, you’re like Spike Lee and probably don’t care about the technical performance of your upturned “Brooklyn” cycling cap—it’s a fashion item, after all. Cotton caps won’t breathe well or keep you particularly warm (especially when your sweat turns cold), but we included our favorite designs from brands like Ten Speed Hero and Machines for Freedom for off-the-bike style.

All of these cycling caps serve a distinct purpose, even if that purpose is solely to stunt on the group ride. We included our favorite waterproof and insulated models, but for the ones we haven’t tested, we based our selections on user reviews from around the web. Then we surveyed the market for the coolest cotton hats around, and added a couple customizable varieties for the most creative cyclists among us.

Castelli’s A/C cycling cap is designed for hot summer slogs. The open-cell mesh fabric wicks moisture and facilitates ventilation. Paired with an airy helmet, the A/C Cap provides sun protection without sacrificing comfort or cooling.

We gave Gore Wear’s C7 Shakedry jacket our coveted Gear of the Year award for its ability to keep the elements out and effectively ventilate sweat. That same packable material is now available in a cycling cap, an ideal companion for rides when rain is a certainty. And despite its blacked-out appearance, a reflective brim logo increases visibility at night.

The Giro Peloton is made from a 50/50 split of polyester and Nanobon, a fabric that uses fibers made from bamboo charcoal. Nanobon is even said to have natural deodorizing qualities, though some people report the hat soaking through quickly on sweaty or rainy rides.

This cap from Assos combines breathability with rain, wind, and sun protection. The center of the cap uses a polyester-cotton blend fabric that shelters you from the elements, while the sides are a breathable mesh that keeps your head cool.

This POC lid uses a poly-cotton construction to blend performance with comfort. A reflective brim logo helps drivers see you in the dark, and an elastic band on the back provides a snug fit. The more generic fit makes this less ideal for wearing under a snug helmet, though.

Pearl Izumi took a big step toward sustainable design when it debuted this all-merino wool cycling cap in September. The lid is exceptionally thin and utilizes recycled Repreve XS Polyester technical fibers (made from old plastic water bottles) to keep it just as light as it is warm.

We’ve all forgotten to reapply sunscreen when out on the road in perfect weather. But no one wants to look like a lobster on two wheels when a bluebird ride comes to an end, so Giro designed a cap with a UPF-30 rating (meaning it blocks your face from harmful UVA and UVB rays). Plus, it’s made with antimicrobial mesh, so it can handle a few sweaty rides and still stay fresh between washes.

Want a hat with a logo of a kangaroo eating pizza or a sassy Anthony Bourdain quote on it? Well, here’s your chance to have it made. Headsweats offers customizable hats with whatever design you can dream up. Or if you desire a really simple, classic cycling cap without frills or kangaroos, the company (based in Boulder, Colorado, and launched by former pro Alan Romick in 1998) still offers a $20 version of the original that started it all.

Machines for Freedom is a company founded by women who are designing kits and accessories with women in mind. That’s why it offers two sizes in its unisex cycling cap, covering all head sizes, though we love the lower volume of the smaller size for women’s heads.

These wildly patterned fabrics have plenty of stretch and elasticity and are sure to catch the eyes of drivers and other riders. Aside from having plenty of cartoons to choose from, (Big Bird? Grinch, anyone?) these caps are technical and lightweight, with moisture-wicking and breathable bodies and light, flexible brims that fit well under most helmets.

This bright, splashy cycling cap is made of 100 percent polyester, but has a slightly denser weave and tougher finish than some others on this list. You’ll pay a very minor weight penalty, but the more rugged surface means it can be rubbed and abraded without pilling. This is a great town look as well, so you won’t feel too ~sporty~ wearing it to happy hour after your ride.